Three weeks of writing every day. Three weeks of being as active as I’ve ever been. And this morning, sitting with a podcast in my ears, I had to admit something: nothing’s changed.

I was listening to Blake Mykowski’s interview with Gabor Maté on No Magic Pill. I put it on because I’m trying to figure out what I’m actually doing in the world. Who I am. What I’m building toward. I left my old life and told everyone, including myself, that it was to find something more meaningful. Looking at it straight this morning, that wasn’t quite true. I was just pointing the same status and the same ego in a new direction. It felt different. It wasn’t different.

Maté spends a lot of the conversation on how much weight rides on parents being emotionally present for their kids, and how most of our trauma, capital T and lowercase t, traces back to an early wound.

Then he turned it on Blake. Pushed him on what he’s actually doing with his Enough movement, all the mental health content, the mission of it. And it landed on me because it sounded exactly like what Maté described doing with another guest earlier, someone chasing “enough” by making the big splash, the big impact. I’m not certain I have that name right, so take it loosely, but the pattern was unmistakable. Making a big impact to prove you’re enough is still ego. It’s just ego wearing a nicer outfit.

Sitting here this morning, I saw the same thing in myself. My mind is still on success. Still on work. Still on finding the path, instead of putting all of that down and just living the life I actually have. Which is: raise my boys. Be a husband. Be an Orthodox follower of God. That’s it. No more.

There’s real freedom in saying that out loud, even if I’m not entirely sure what it means practically. Ultimately, I still need income, but I can craft a story around what that income should look like. The reality is, fulfilling a family’s needs requires very little. It doesn’t have to come from my own business or follow an entrepreneurial route that others admire.

It can be simple, off LinkedIn, off Substack—something that just pays the bills so I can focus on the work only I can do: loving my boys, my wife, and loving God. That’s enough. The key today might be to ask whether the income source you pursue needs to be impressive or just effective.

I’ve been writing these posts daily for three weeks now, and honestly, it’s been fun to write again. But I noticed something else this morning. This is another version of the same move. Another way to prove to people I’m enough. That I’m worthy. That I’m doing something productive I can point to.

So I’m slowing down. Instead of daily, expect something from me maybe once a week, longer and more considered.

What I’m reading. What I’m thinking about. It will be less about what I’m building, but more about who I am becoming.

Appreciate you all. Thanks for riding along.

Foley

You don’t need reps who write better emails. You need to hit the number.

That’s the whole test as a VP of Sales.

It's not just about whether “the deck looked sharper,” or “the rep sounded smarter on the call,” or if “we shipped more content.” If it doesn’t show up in metrics like close rate, ASP, cycle time, or bookings, it isn’t really making a difference. Many sales leaders who are currently using AI are focusing on the wrong areas of this test. They’re using Claude to write follow-up emails and summarize call notes, which is okay. But, honestly, that’s just scratching the surface of what the tool can do.

It’s the way you listen to a discovery call and know, in the first four minutes, that the rep skipped the agenda and is about to lose control of the deal. It’s the way you look at a forecast category and know which “commit” deals are actually a coin flip. It’s the way you run a 1:1 so the rep leaves with one thing to fix, not five.

That judgment is why you have the title. It’s also completely trapped in your head, available to exactly one person, for exactly as many hours as you’re awake.

Claude Skills is the mechanism to get it out of your head and into your org, without writing a line of code.

What a Skill actually is

A Skill is a folder with instructions, at least one file: SKILL.md. This file has two parts: a short frontmatter with name and description (max 200 characters) that explains what the skill does and when to use it, and plain markdown with detailed instructions. For complex skills, you can add reference files, examples, or scripts. Most of this work is writing clear, concise instructions, not software.

You turn Skills on in Customize > Skills (this requires code execution to be enabled on your plan). From there you can either upload a skill you built as a folder, or use the built-in skill-creator, which interviews you and drafts the SKILL.md for you. Once a skill exists and is toggled on, Claude decides when to use it. You don’t have to remember a command.

You ask for the thing, and if your description is good, Claude reaches for your skill instead of guessing from scratch.

The part that matters most: a skill built this way works the same whether you’re in a normal Claude chat, in Cowork, in Claude Code, or via the API.

Build it once, over the weekend, and it’s available everywhere you work from that point forward.

Step 1: Map the job before you touch a keyboard

Before you build anything, write down every discrete thing you actually do. Not “sales leadership.” The actual tasks. Use Wispr Flow or just talk into your phone and get it into a doc, then dump the whole thing into a Claude project and ask it to turn the ramble into a clean, numbered list. You’ll end up with something like this:

• Reviewing overall pipeline

• Reviewing a specific deal against your methodology (MEDDPICC, Command of the Message, whatever you run)

• Running a 1:1

• Coaching a rep after a call, based on what actually happened on the call

• Auditing and improving sales assets (decks, one-pagers, email sequences)

• Interviewing a sales candidate

• Running an enablement session

• Building an enablement deck

• Forecasting: pipeline movement week over week, stage integrity, forecast category discipline, rep-by-rep behavior patterns

• Rolling that into a spreadsheet and mapping close rates by stage and by time in stage

• Applying your judgment to the raw number, then loading your call into whatever forecasting tool your org uses

• Running the forecast call itself: which deals get pressure-tested, which ones you take on faith

• Sizing the biggest deals in the funnel to put a plus-or-minus on your number

• Rolling your team’s forecast call up into your own leadership forecast call

• Tracking pipe generated, by rep, by week

• Analyzing where pipeline is actually coming from, so you know what to double down on

• Drafting follow-up emails on stuck deals

• Helping a rep get unstuck: bringing in an exec, reframing the story, finding a new way into a stakeholder

That’s roughly seventeen distinct jobs. Each one is a candidate for a skill. Don’t try to build all seventeen Saturday morning. Pick the three or four that eat the most of your week, and start there.

Step 2: Build the skill by teaching, not by prompting

This is where most people get it wrong. They open a chat and type “write me a rubric for coaching sales calls.” That gets you a generic rubric. It doesn’t get you your rubric.

Here’s the actual process, using post-call coaching as the example since it’s the highest-leverage one for most sales leaders.

Open a new chat and ask Claude to use the skill-creator to help you build a skill for coaching reps after a call. It will ask you clarifying questions before it writes anything: what methodology you run, what a good call looks like to you, what “bad” actually sounds like. Answer honestly and specifically. Vague answers produce a vague skill.

Then go get a real call. Pull one from Gong, Granalo, or Fireflies. If your org has an MCP connector set up for either tool, pull it in that way. If not, just download the transcript and upload it directly to the chat; that works fine too.

Now do the part that actually builds the skill: coach the call yourself, out loud, in the chat. Not a summary. Your real reaction, sentence by sentence. “I’d flag this open, no agenda was set.” “This is the moment they should have asked a second-level question and didn’t, here’s the follow-up I’d have used.” “We never got a real next step, we got a maybe.” “This close is too soft, given where they are in MEDDPICC.”

Use Wispr Flow if talking is faster than typing. The point is volume of your actual judgment, not polish.

Ask for a V1. Now you have something concrete to react to: does this sound like the coaching you’d have given? Where’s it off? Too soft, too clinical, wrong tone, missing a step you always take? Correct it directly, the same way you’d redline a rep’s email.

Feed it more calls. Once V1 feels close, run it against ten or fifteen more transcripts and see where it breaks. A bigger sample surfaces the edge cases: the call that went well despite a shaky open, the rep who’s naturally quieter but still in control. Fold those corrections back in and you’re at V2, then V3.

You’re done when the output would pass as something you wrote. That’s the actual bar. Not “this is helpful.” “This is what I would have said.”

From here forward, any call becomes: drop the link or upload the transcript, ask for the coaching breakdown, and it comes back in your voice, using your framework, calibrated to your standards. You didn’t just save time on one call. You built a piece of infrastructure that outlives any single week.

Step 3: Put it on a schedule instead of running it by hand

Once a skill is solid, the next move is to stop triggering it manually. Claude Cowork has scheduled tasks: you describe a job once, set a cadence, and it runs on its own from there, with access to the same skills, connectors, and tools you’d have in a live session. So instead of remembering to pull each rep’s calls and run the coaching skill yourself, you set up a recurring task: pull yesterday’s calls, run the coaching skill against each one, and save the output somewhere your reps can get to it. Worth knowing going in: scheduled tasks on Desktop only fire while your machine is on and the app is open, so if you’re picturing something running silently overnight on a laptop that’s closed, check the current setup before you build around that assumption, since this is an area Anthropic has been actively shipping into.

The same pattern applies to a forecast rollup. Build a skill that takes your team’s raw pipeline export and produces the stage-integrity and coverage view you actually use in a forecast call. Schedule it weekly. You walk into your own forecast call with the analysis already done, and you spend your time on judgment, which deals are real, instead of building the spreadsheet that gets you there.

The skill stack: what a VP builds this weekend

Here’s the list from Step 1, reorganized into an actual build order. Start at the top.

Pipeline and forecast

1. Weekly pipeline movement and stage-integrity report, built from a raw CRM export

2. Coverage and velocity analysis by segment or territory

3. Close-rate-by-stage-and-time model, for calibrating your forecast number

4. Forecast call prep: flags the largest and riskiest deals for pressure-testing

Deal and rep judgment 5. Post-call coaching, in your voice, against your methodology 6. Deal review against your qualification framework, done before a deal hits forecast 7. Stuck-deal unblocking: drafts an exec outreach angle or a new stakeholder path

People and enablement 8. Candidate interview scorecard and follow-up questions, built from your actual bar 9. 1:1 prep, pulling the rep’s pipeline, activity, and recent call trends into one page 10. Sales asset critique: reviews a deck or one-pager against what actually converts 11. Enablement deck builder, seeded with your talk track and objection handling

Pipeline generation 12. Pipeline source analysis: where bookings are actually coming from, by channel and rep 13. Follow-up email drafts on stalled deals, in your tone, referencing deal-specific context

Thirteen skills is a real weekend’s work, not six hours. Build two or three well before you build thirteen badly. A sharp coaching skill and a sharp forecast-integrity skill will do more for your number than eleven mediocre ones.

If you actually want to do this in one sitting

Block six hours. Here’s roughly how to spend them.

Hour 1: Map the job. Dump every task from Step 1 into a doc, however messy. Don’t edit yet, just get the full list out of your head.

Hour 2: Pick your first skill and build it with skill-creator. Answer its questions specifically. This is the hour that determines whether the whole exercise works, so don’t rush it to get to the “fun” part.

Hours 3-4: Teach it on real deals. Pull two or three real calls or two or three real forecast exports. Coach them, correct them, react to the V1, get to something that sounds like you. This is the slow, unglamorous part, and it’s also the part nobody skips if they want a skill that’s actually worth using Monday morning.

Hour 5: Stress-test it. Run the skill against five to ten more examples you didn’t use while building it. Watch for where it breaks, where it’s too generic, where it misses something you’d have caught. Fix the instructions, not just the output.

Hour 6: Build your second skill, faster this time. The first one always takes longest because you’re learning the process along with building the thing. The second one goes quicker because you already know what “specific enough” looks like.

You won’t leave the weekend with thirteen skills. You’ll leave it with two or three that actually work, which is worth more than thirteen that don’t.

The part that’s easy to miss

None of this replaces your reps’ job, which is selling, or your job, which is judgment at scale. It’s the opposite of replacing it. A skill built the way described above is worthless without your judgment in it first. The AI isn’t the asset. The instructions are the asset, and the instructions are just your expertise, written down once so it can run without you standing there every time.

That’s the actual shift. Most sales orgs using AI right now are using it to make individual people faster at individual tasks. That’s a productivity tweak. Turning your judgment into a stack of skills that runs on a schedule, coaches every call, flags every risky deal, and preps every forecast before you open the spreadsheet- that’s not a tweak. That’s the org running on your standard, not your bandwidth.

Six hours over a long weekend. Two or three skills, built properly, fed real deals and real calls until they sound like you. That’s the whole exercise. Print this out, block the time, and go build it.

Some mornings I open the crate, look at everything in it, and feel nothing pull.

That’s the honest version of where I am right now. There are three real things in there. A software product I could build. A fractional practice I could scale. A consulting firm I keep sketching out on the biggest possible canvas. Any one of them could work. And I don’t have a strong conviction about any of them.

Nobody tells you that the hard part of starting over isn’t the work. It’s the not-knowing. I can outwork most people. What I can’t do yet is point at one thing and say, that one, I’m all in, everything else goes back on the shelf. So I keep them all half-alive instead. Three things at forty percent. None at a hundred.

It’s a specific kind of stress. Not the sharp kind you get before a big number closes. A low, constant hum. The feeling of standing at a fork with three roads and no map, and knowing that standing still is also a choice, and it’s the worst one.

And here’s the part I don’t say out loud much. Some nights the old path calls.

I know how to run a sales org. I took one from zero to $xxM ARR in under eight quarters. I could email three people this week and probably have a VP or SVP seat by next month. Real comp. A team. A playbook I already know cold. The version of me that’s tired looks at that and thinks, why am I making this so hard?

Because the seat isn’t mine. That’s the whole reason I left. But conviction and exhaustion don’t always keep the same hours, and at 11pm the exhaustion is usually winning.

I don’t have a clean lesson to hand you today. I’m not going to pretend the fog is actually clarity in disguise. What I’ve got is this: I’d rather sit in the honest discomfort of not knowing than take a seat I already know doesn’t fit, just to make the humming stop.

Ask me again next week. The answer might be different. That’s kind of the point.

Foley

I counted my calendar so far this week. Seven conversations that had nothing to do with an existing client, a signed deal, or anything I could point to and call “the plan.”

• A coffee with a state government contact who’s been introduced around town as someone reinvesting his time in local builders.

• A call with a VC and a well-known author about something they’re working on together.

• An intro call with a founder building a talent platform. Another with a founder in the insights space.

• A breakfast with two guys building something in the local game space.

• A standing catch-up with a friend who’s building his own thing.

None of them were on my calendar because I had a plan for them. They were on my calendar because someone asked, and I said yes.

This is the part of “finding the idea” that doesn’t photograph well. It’s not a whiteboard session. It’s not a framework I ran once and got clarity from. It’s thirty-minute conversations, back to back, most weeks, most of which go nowhere specific. I don’t have a filter for who gets a yes right now. If someone wants to talk about what they’re building, I take the call.

I used to think that was inefficient. I still catch myself thinking it. There’s no dashboard that tells me which of these seven calls this week matters. Most of them probably don’t turn into anything I can point to in six months. But I’ve stopped needing each individual call to justify itself, because that’s not the unit that’s working.

The volume is the unit. Somewhere in the stack of unrelated conversations, patterns start to repeat: the same problem described three different ways by three different people, the same gap nobody’s filled, and the same question I keep getting asked that I don’t have a canned answer for. You don’t see that pattern in one good conversation. You see it in enough conversations that the noise starts to sound like signal.

Here’s the tactic, if you’re in the stage I’m in: stop waiting for the idea to arrive as a single clean insight. Book the calls. All of them, even the ones that seem unrelated to whatever you think you’re building. Say yes to the coffee with someone you don’t know yet doing something you don’t fully understand yet. The idea doesn’t show up in the room where you’re alone thinking hard. It shows up as an accumulation, and you don’t get to pick in advance which conversation has the piece you need.

The honest cost of this is that it’s exhausting in a way that’s hard to explain to someone who hasn’t tried it.

Every call is a small performance. Introduce yourself, explain what you’re doing, listen for the thread, decide in real time whether to pull on it. Seven times in a week. I don’t have a clean answer yet for how long I can sustain that pace, or when the volume tips from generative into just busy.

I just know that right now, it’s the only method I’ve found that’s actually working, and sitting alone with a notebook wasn’t.

Foley

Today felt like the kind of day I left for. Not easy exactly. but alive.

Breakfast at 8:30 with someone running entrepreneurship initiatives at the Indiana Department of Commerce. We had an interesting conversation about how they could use AI tooling more effectively to drive stronger citizen engagement.

Fun one.

Then I had a speaker discovery call teed up by a VC as I continue to pursue the Milkcrate concept.

The original hypothesis was pretty simple: experts need an all-in-one tool to run their business. I think that hypothesis has mostly been disproven.

After enough conversations with speakers, coaches, consultants, and experts, I don’t think the core pain is “too many tools.” The pain is growth. The pain is pipeline. The pain is turning expertise into a durable business.

So I still believe there is a platform play for non-physical SMB companies. I just think it probably starts somewhere more obvious.

Websites. The website is the front door of the business. It is where positioning lives, where the offer shows up, where trust is built or lost, and where many of these businesses still feel way behind.

So, back to the drawing board. But not off the board.

I also had a follow-on call for another fractional opportunity and I’m starting to get the sales process down a little better.

The thing I’m building for this work is what I’m calling a “pipeline catalyst.” Basically, it ingests a bunch of pipeline and customer data, applies my interpretation of the gaps, and spits out a 4–5 recommendation proposal.

I’m building it as a Claude skill, which I didn’t even know existed until a couple of weeks ago. But it has basically become a way to create my own little internal products for recurring tasks and analysis.

The best part is that I can train it to analyze data more like I would. Not perfectly, but close enough that I can keep going back and forth with it until the output gets to a place I actually like.

I ship my first one to a client this week.

Then I went onsite for a consulting proposal I’m working on, which is tied to the same work above. I find it fascinating to dig deep into GTM data and try to understand which levers could actually drive growth.

Right now, I’m doing a lot of it for free. Probably 10+ hours for this one client. And the strange part is, I genuinely enjoy it.

I enjoy finding the story inside the data. I enjoy looking at the pipeline and trying to figure out what is real, what is fake, what is stuck, what is underpriced, what is under-resourced, and what one or two moves could change the trajectory.

I’m trying to learn to trust that.

I ended the day going back and forth with Claude on the pipeline catalyst skill.

It was frustrating. The outputs are not magic. There is still a lot of shaping, pushing, and correcting.But they are pretty good. And it saves me a ton of time.So it feels worth it.

Days like today energize me because of the variety. Seven meetings across state government, AI consulting, speaker businesses, SaaS GTM, and fractional work.

That is fun for me. It also fries my brain. So I’m trying to stay in the discomfort and not jump too quickly to anything. There is a version of me that wants to turn every interesting conversation into a job offer, but I’m doing my best to not give in.

I think the job right now is to keep paying attention.

What gives me energy? What are people actually willing to pay for? Where do I have a real edge? Where am I forcing a thesis because I want the story to be clean?

No big lesson today.

Just a full day, a fried brain, and a few more breadcrumbs.

-Foley

I spent all week bracing for the weekend.

My wife was traveling, the two boys were mine, and I had already written the story in my head. High stress. Low joy. Survival mode until she got back.

The opposite happened. I enjoyed it.

Not in the grit-your-teeth, cherish-every-second way you are supposed to say you do. I had a genuinely good time. Solo parenting was supposed to be harder. It turned out easier.

This was not because my wife does less. She is an incredible mother who carries more of this family than I do.

So why was it easier with her gone?

I have been turning that over all morning. Here is my first honest pass.

1/ The first thing is that I had no options. None.

The culture tells you to protect optionality at all costs. Take the job that opens the most doors. Keep your hobbies. Stay curious, stay open, keep every lane available. I am the worst offender, at least where work and ambition are concerned. It runs as a constant background process. What could I be doing right now? What should I be reading? Which podcast am I behind on? Should I take up pickleball? Should I start running again? Am I having enough fun? Is the money going to run out?

The psychologist Barry Schwartz called this the paradox of choice. More options do not make us freer. They make us anxious, because every path we did not take becomes a small loss we carry around.

This weekend the options vanished. I was the only thing standing between two small boys and total chaos. There was no productivity shame, because there was nothing else I was allowed to be doing. The book, the business, the side quests, all of it was off the table.

And I felt something I almost never feel. Peace.

The Stoics had a name for the move I stumbled into.

Epictetus divided the world into what is up to us and what is not, and said that freedom lies in letting go of the second.

My options did not actually disappear this weekend. I just stopped being responsible for them. The pressure I had been carrying turned out to be self-issued. Chains I forged and locked myself into, holding the key the entire time.

2/ The second thing is harder to admit. I am constantly performing for an invisible audience.

I care far too much about how I am seen. My life has been one long audition for love. Sports, school, business, and now marriage and fatherhood. From the outside it reads as drive. Underneath, the fuel is approval, and approval burns dirty. It leaves you tired no matter how well you perform.

More than a century ago, a sociologist named Charles Cooley described what he called the looking-glass self. We build our sense of who we are out of what we imagine other people see when they look at us. I live there. As a husband and father, I am always running the scan. Am I doing enough? Is she watching us play? Does she think I am a good dad? I keep hoping she will tell me that I am.

To be clear, my wife does not do this to me. The wiring is mine.

It shows up everywhere.

At work, I wanted to be the first to answer Slack, the first to comment on the doc, not because the answer was burning to get out, but because I wanted to be seen as the hardest worker and the smartest person in the room.

With hobbies, I will not even start something if I cannot be good at it, and when I do play, half my attention goes to reading the room for approval.

This weekend there was no room to read. No audience. For two days I could just be with my boys without scanning their faces, or anyone else’s, for a grade.

I spent zero minutes on work, hobbies, or entertainment. It was one of the best weekends I have had in a long time.

So here is the work now, the real work, done day by day. To believe that who I am is already enough. There is no audience. You do not need to produce anything more than you already are. Full stop. Nothing past that.

It is 8 am. I am writing this at the kitchen counter, and I can already feel the old machine spinning back up, asking whether sitting here is wrong, whether my wife is quietly starting to resent me, whether the boys will grow up remembering a dad who was never really there. But here I stay. Typing. Hitting send while the fear is still in the room.

With gratitude,

Foley

As I’m having breakfast with a few local VCs today, it clicks somewhere in the conversation. I could build that.

An AI-native GTM agency.

Take everything I’ve used to build high-growth sales teams and turn it into something a company can just buy, with a high-end service component on top. De-risk their growth. Stop making them throw headcount and internal resources at it. Same outputs, less weight.

[If you haven’t heard of AI native service companies, or what the cool kids are calling AINS, check out more here.]

So I started pulling everything I’ve ever built into one Claude project. Emails. Docs. Decks. Call recordings. Models. Eight years of go-to-market in one place, so I could frame out what this could even look like, because I’ve never built anything quite like it.

VCs like a16z and Emergence are backing firms built this way from the ground up (see here, here and here). The part I can’t stop thinking about is where these companies stand. McKinsey at one end. Stripe at the other.

That’s the question I keep noodling on. How do you build a best-in-class services business and a best-in-class product business at the same time?

I don’t have the answer yet. But the pull is real. The market already pays for software wrapped in services. Now you can run services that scale like software, and the customer gets a better product as a result.

Here’s the actual move, if you want to steal it. Put everything you’ve ever built into one project and tell the model exactly who it’s supposed to be. Mine looked like this:

“You are a third-year associate at an elite VC firm. Stanford and McKinsey before that. Build me an investment thesis for my investment committee: problem, hypothesis, product, founder. Then pressure-test it as any investor would. Why wouldn’t someone else do this? How does it break? What is the appropriate initial wedge? What is a reasonable TAM? SAM? Give me the anti-arguments against you. Ask me any questions you have before executing.”

The default setting on these tools is flattery. You have to make them argue against you.

The two questions I run every idea through now:

1/ is the work being outsourced today as high-volume, high-importance, low-judgment?

2/ is it already being outsourced through a SaaS product?

When both are yes, it’s worth exploring, but only if you have domain experience. These businesses depend on the founder’s specific knowledge and skills, making them especially intriguing for those who have been in the game for a while.

All of this makes me realize there’s a fourth variable I’m adding to my list of what I want next. It used to be three. Creative, building, local. Now I’m adding owning. I want the direction to be mine. I want to point at the thing and know I built it.

-Foley

Why?

They all started with a single problem that was also the tip of the spear for an entire workflow.

Offer letters. Rippling started with an offer letter generator. Why? The offer letter is the first thing an employee signs when they join a company. Nail that one document and you have a foot in the door to the entire HR stack. Onboarding, payroll, benefits, devices, all of it. Start at the signature and you earn the right to everything that comes after it.

One order off a PDF. DoorDash’s first version was a landing page with a few PDF menus and a phone number that rang their personal cells. Their first order (Thai if you are interested) came a few hours later. One of the founders picked up and dropped it off himself. That single order off a single PDF was the entry point to every kind of online delivery. The one workflow taught them everything. The restaurant side, the driver side, the customer side. They earned all of it by running the smallest possible version first.

One bank connection. Plaid set out to build a consumer budgeting app and kept hitting the same wall. They could not connect to anyone’s bank. So they realized the connection was the actual product. You cannot send, spend, borrow, or invest in any app until your account is linked. That one step is the front door to all of fintech. Plaid built the front door and became the rails underneath Venmo, Robinhood, and Coinbase.

Cap tables. Carta ran the same play on equity, and it shows you how to generalize the move. Henry Ward started Carta, then called eShares, by digitizing a single paper stock certificate for twenty bucks a pop. Boring. But the cap table is the atom of who owns a company. Capture how shares get issued and you own the ownership record itself. From that one record Carta built 409A valuations, then fund administration, then a private stock market. Liquidity was always the goal. The cap table just had to come first.

All of these founders went to the simplest possible unit of the most critical entry workflow. Small enough to test in a short, cheap way. Upstream enough to hand them unprecedented access to every downstream workflow.

They went as far upstream as they could, to the very first step, built there, and grew from there.

So if you are thinking about starting something new, ask yourself: what is the very first action {x person} takes when doing {y thing}? Find the record that gets created the moment the thing is born. Own how it gets made. Build the rest on top.

Here are a few “atoms” that I could think of off the top of my head.

School applications. Every single student has to fill out an application to enroll in a K-12 district. The student record is also the atom of the Student Information System. Build a better tool for enrolling students and you can potentially build a compound product to take down PowerSchool.

Patient intake. The first thing that happens in healthcare is not a diagnosis. It is a clipboard. Every patient fills out an intake form before they are ever seen. That intake is the atom of the medical record, and the medical record is the thing every other system in the building bends around. Own how a patient gets entered and you have a wedge at the one place the entire EHR is built on. That is the soft underbelly of a company like Epic.

Email address. At the core of capitalism is selling a product to a customer. In our digital landscape the first opt-in a customer makes with you is an email signup. Almost every interaction from there on out starts with the email. So if you want to build the next gen marketing automation platform, think from first principles about how you capture that email in the first place. The website. I think this is what Bryant Chou is doing at Ploy, and it’s why I am so bullish on it.

Please comment or reply back with any other atomic examples you have!

-Ben

Today was a good day. I had a one-on-one with a former peer, caught up with a college friend, and reconnected with a close colleague. All three are high-slope professionals aiming to leave the tech rat race and establish or buy a meaningful local business to run long-term.

An idea that stuck with me from my own dialogue: I want to build something that my boys can take over. I want to build something they can point to and say, "That's where my dad works."

I know this sounds ridiculous in our world of remote work and AI, but I want that, and I’m not even sure why.

I want the physicality of work, the physicality of human experience. I want to see and feel the people I work with interact in the real world, watch them grow and flourish, and build a community.

That's what we were made to do here: build community and build a life. Work was how we supported that life. For me, at least, I've gotten that upside down and tried to fit my life into the work.

As I continue on this path of building, creating, and doing it locally, I'm leaning toward businesses I can run without venture capital, businesses I can run locally, businesses I can build and that impact the community, and businesses my boys can take over.

The crazy thing is, I hear the same desire from almost everyone I know who has a high-powered job at a VC-backed tech company. We're all looking for something, and not everybody can put their finger on it, but it looks a lot more like tribe and a lot less like chatbots, Slack, travel, and async.

I'm long on sync, long on face-to-face interaction, and long on 3D.

brick by brick,

Foley

Seven years ago, I started a blog called Fully Rich Life. It was about mindfulness and how you could use it to reduce anxiety. I built it to a 10,000-person email list and launched a product that made about 15k in a weekend. Then I dropped it all to get back on the career path. The status-seeking path.

That path ultimately led me from an AE selling signatures to VP of Sales at an $8B tech company, where I led a team of 60. The team was doing well. I had great people under me. The opportunity in front of me was massive, and the demands weren’t too high. And I felt completely empty. No creativity. I wasn’t building anything. I was working fully remote, in an office by myself again, and I knew I needed to change something.

So about two months ago, I started writing again.

I still had around 3,000 Fully Rich Life subscribers I hadn’t talked to in a couple of years. I ported them into Substack. I have no idea why I chose Substack, but I did. I sent one email telling people to unsubscribe if they didn’t know who I was or didn’t want to follow along. That dropped the list to 2,500. Then I started writing.

At first, I had no idea what to write about. What would anybody want to hear from me? But I knew a lot about sales, high growth, hiring, RevOps, and go-to-market for high-growth, venture-backed companies. So I started writing long-form essays about that.

At the same time, I was interviewing. I was interviewing eight to ten incredible venture-backed companies, Series A to Series C, with $15-70M in ARR, ~$500k OTE, 1% equity. These were companies I couldn’t have imagined getting a shot at eight years ago, when I started this journey. And almost every one of them required me to move. Deep down, I didn’t want to move forward and felt unable to continue those processes. Perhaps I burned a few bridges by quitting, but I kept writing regardless.

I also wanted to build something. The first idea was ClearDate. From my time at Flock, I’d seen how broken the system is for getting people back on their feet after prison. One in eight people is in prison because they didn’t show up for a court date. If you’ve ever had to pay a parking ticket or deal with your local municipality, you know how horrible that process is.

The second idea was a Duolingo for sales. Enablement is a huge bottleneck in most go-to-market motions, and it’s almost always a classroom setting. From my time at Edia, I’d learned the best way to teach is one-to-one, dynamic, and micro. So I went on LinkedIn, found ten to fifteen engineers at Duolingo, and cold-outbound them.

One responded, Andrew, a high-slope engineer, earlier in his career. We went back and forth on the product, talked to some VCs, and got a few people using it. But sales training is so expert-dependent. Everybody has their author, their methodology, their guy. Building a third party that wasn’t aligned with one of those would be really hard, and monetizing at the rep level would be even harder. Most salespeople don’t want to do enablement anyway. You never want to sell a product where you have to tell people to do the thing it’s supposed to do. So I put it on the shelf.

Then, six weeks ago, I officially left my job.

I told a few people I wanted 30 meetings in 30 days with people in the Indy building who are creating and running companies. I ended up with 82 meetings in 6 weeks. Maybe compulsive. But I learned a ton about the ecosystem, and more about myself. I love being in person. I love the meetings, getting people on the hook, driving toward the next one, asking a ton of questions. I found multiple jobs that way. I didn’t want any of them.

During that stretch, a buddy from college who’d been reading some of my articles reached out for coffee. He’d built a really successful consulting business locally and was struggling to figure out how to grow it. In that first meeting, we broke down the business, how he was selling, and who he was selling to, and I suggested he go all in on a single vertical. It worked. We had three or four more meetings, no charge, and he found a lot of value. He became my first paying consulting gig.

I kept iterating with Andrew. One of the projects was Milk Crate, an agentic platform for experts. I was building my own fractional go-to-market and content practice at the time, and I noticed how many different tools these people use to go from zero to one, and from one to ten. I thought there might be a huge opportunity to build one all-in-one product. I went deep, talked to a bunch of VCs, got some real interest, and Andrew and I started building. I had more than ten calls with speakers, coaches, and consultants. I found them online and reached out directly, asking for ten or fifteen minutes to learn how they run their business. Eight of those calls went deep. I took detailed notes. And what I realized is that their pain wasn’t having too many tools. Their pain was building durable businesses and building outbound pipeline. So, back to the drawing board.

The whole time, I was also wrestling with the blog itself. What should the title be? How often should I post? Does anybody even care? How often on LinkedIn? Should I build an Instagram or an X account? What about Beehiiv, ConvertKit? How do I build products? I was trying to find a job, start a startup, build a blog, and build a fractional business all at once.

Then, two weeks ago, it came to a breaking point. All of these incredible jobs required me to move, and I didn’t want to move. So I opted out of the last CRO opportunity I was offered and decided to dedicate the next six months to building something I owned, or to being a very important part of someone else's ownership of it.

Given the Milkcrate idea, I wanted a blog tied to that brand. That’s where Raw Milk came from. And when I dropped out of that last interview process, I felt a deep fear about what I was doing and the life I was giving up. I needed a mechanism to hold myself accountable. So Raw Milk became a daily post: going from no job and no interview process to something.

Now that you have the context, here are the key learnings from the last 6 weeks.

5 things starting over has taught me so far:

1. the thing i was most scared of was the cheapest asset i had.

i was terrified to tell people i’d quit, so i did the opposite of hiding. i told a few people i wanted 30 meetings in 30 days with founders and operators in indy.

i had 82 in six weeks.

i didn’t find a plan in those rooms. i found out what i actually like. you don’t think your way into that. you talk your way into it.

2. “free” was the best sales motion i ran all month.

A buddy from college read some of my writing and asked for coffee. I broke down his business, told him to go all in on one vertical, and gave him three or four more sessions. No charge, no pitch.

He became my first paying client.

i didn’t sell him. i was just useful in public until paying me was the obvious next step.

3. My thesis was wrong, and eight people told me so.

I was sure experts were drowning in too many tools. that was the whole idea. so i found speakers, coaches and consultants online, cold-reached out, and got 8 of them deep on the phone.

The pain wasn’t too many tools. The pain was building a durable business and a pipeline.

8 real conversations saved me from building the wrong thing for 8,000 people.

4. never sell a product that requires people to do the thing you’re selling.

I tried building a “Duolingo for sales.” Then it hit me: most salespeople don’t want to do enablement in the first place. and every expert is loyal to their own methodology.

I was selling a behavior nobody wanted, to a buyer who already had a guy.

I shelved it. that sentence is now a filter i run every idea through.

5. Status and ownership pull in opposite directions.

The jobs were real. series a to series c, $15-70M arr, the kind of roles i couldn’t have imagined eight years ago. Almost all of them required me to move.

Something in me wouldn’t do it.

i can’t fully tell if walking away is conviction or ego. i’m choosing to find out.

i have friends and family texting to ask if i’m okay. it stings. i have no idea what i’m doing.

But I’m writing this down every day so i can’t quietly back out. and so far, i’m grateful. I hope it’s helpful for you.

Foley

Friday was a good day. Landed three net new meetings for fractional. Had my first couple thousand dollars hit the bank account and ultimately ended the week on a solid trajectory.

However, over the weekend, I spent far too much time going back and forth with my buddy Claude on “wedge ideas.” For some reason, I still have a belief that one day I’ll prompt him (her? It?) in just the right way that he gives me certainty of future success and glory. So far, no dice.

So as I sit here on a Sunday night, rain coming down, in the screened porch, candle going, the withdrawals of not having status or a job or a clear path forward hit hard, or like the kids say, ‘it slaps.’

I expected anxiety on the journey, but this is the type of anxiety that makes you rethink your identity and realize that you may not have an identity outside of the job and career you left behind.

I know many people have gone through this on the path but man, being at the beginning of it, I can't wait for the end of it to come.

Grateful I have people in my corner that aren't telling me to turn back because that road might be easier.

I hope I continue to have the strength to move forward.

What I’m starting to realize is that even success pursuing something I’m passionate about won’t heal the wounds of insecurity. Those can only be healed from within.

Maybe that's part of the journey, maybe that's part of the learning, maybe that's the whole point of this.

Thanks for following along.

-Foley

Last night at 8:36, I emailed myself a subject line: “pivoting milkcrate.”

New idea —> kill the platform play and build the marketplace that replaces the middleman. Automate what they do, and you’re sitting in the middle of the transaction.

It felt good for about twenty-five minutes. Then I emailed myself again: “Damn. Really small TAM if we go after this slice. I’m thinking too small. I want to build a meaningful company, not a niche one. May need to go back to the drawing board.”

one hour. one idea. one self-rejection. that’s what ideation looks like at 8pm, six weeks in, with nothing locked.

but here’s what i couldn’t see last night and can see this morning: the market has been voting this whole time. i just kept arguing with the result.

By the end of today, I’m pivoting again.

the no’s

9:01pm I tested the bureau idea with two speakers I’m already working with. Same answer from both. The model could work once you prove it, but a monthly subscription is a hard no because they’ve already paid for promises that didn’t deliver. One offered me a 20% commission on a booking, not a dollar until she saw results. The other forwarded a screenshot of a platform she already pays for. Zero leads. Her words: “There are a ton of options out there that promise a lot for an upfront fee and never deliver.”

I forwarded both replies to an investor at 6:33 this morning. useful data. uncomfortable data.

The yes’

Then look at what came in the other door.

• 6:42am — a seed-stage founder in public safety ai replied to the fractional cro pitch i sent this week. “definitely interested.” best reply i’ve gotten on the fractional side in two weeks.

• 11:34am — A VC contact introduced me to another public safety AI founder. Replied in three minutes, locked a call for Friday. Overlaps the sled vertical I’ve been building around.

• 11:34am — An edtech founder I advise came back asking for another hour of my time. Inbound. I didn’t chase it. Coffee Friday.

And the line from my own notes at 11:07 I can’t unsee: fractional cro is “the only place I’ve made money so far.” $xk/month from a fractional engagement. Milkcrate has made zero.

Here's where I landed:

The product ideas keep getting a polite no from the people who’d have to pay. The fractional work keeps getting a yes — real money, real inbound, real calls on the calendar.

I’ve spent six weeks trying to talk myself into the harder story. Today I decided to stop. I’m doubling down on building a GTM services/fractional CRO business, and the gravity keeps pulling toward SLED because that’s where the recurring money is and where the new pipeline overlaps.

But if I’m being honest, it feels small. Like I’m doing it for “the lifestyle and to get away from the grind” (for real, a CEO I talked with said that to me…). I don’t know why that stings so much, but it does.

What you can steal from today

test your price on the people who’d have to pay it, before you build anything.

last night i pitched a brand-new business model to two real potential customers in one evening. Both said no to the subscription. Both said commission-only might work, but only after they see results. that’s not a maybe. that’s the market handing you the exact terms it will accept, for free, in under an hour.

i didn’t lose those conversations. i got the answer before spending six months building the wrong thing.

If you’re sitting on a pricing assumption that you haven’t tested, send two emails tonight. Ask the customer. Hear the hard answer now before you spend years building something no one will pay for.

signal of the day

The LinkedIn alerts keep coming. Today: VP of Sales at a cloud AI company, Head of Sales at an AI startup, and SVP at a software firm. All six figures. All landing in my inbox because I used to be the guy who got those jobs.

If I’m being honest, I’m tempted, but I didn’t engage. What I don’t know yet is whether the story I’m writing instead is better. But it’s mine.

foley

Nobody warns you about the silence.

For years, my phone was a problem I kept trying to solve. Slack notifications were my dopamine hits. Projects to tackle. Emails to answer. A calendar so dense it was proof that I mattered.

Then I left.

The next morning, everything had disappeared. No invites, no fires, no red bubbles on my Slack app to whisk away. The spaces I used to point to as who I was were now silent, empty.

And now, when people ask what I do, I hear myself fumble the answer, and I watch their face make that small, polite gesture it does when someone tells you they “left to figure out what’s next.”

I used to make that face at other people. Now it’s pointed at me.

I think a lot of people stay in jobs they’ve outgrown to avoid that exact feeling, and I understand why. It’s not pleasant to discover how much of you was tied to the pace. the demands. the status. the way it feels to be needed.

I don’t have a neat ending for this. I’ve been five weeks into the quiet. Some of it is easing, some remains. I wanted to write it down before I forget how it felt, because if this process succeeds, I might be tempted to skip this chapter, and that would be a lie.

Daily Log

8:01 AM. En route to an event. I’m sending myself notes about design partners, and a question falls out that I haven’t asked this way before. Thanks, Whispr Flow, for accommodating my compulsive need to move my ideas forward.

8:08 AM. Email back to the engineer I’ve been circling since May. He had a $5K proposal on the table for a version of this product that no longer exists. I tell him the truth: the product changed, there are VCs circling, and I’m not sure equity is the right path yet. Then I ask him to come build something more ambiguous, alongside design partners, before we know exactly what it is. I sent the deck so the word “ambiguous” has edges. No reply yet.

8:30 AM. A room of vertical SaaS people and investors. Same reason every Indy tech room earns the calendar slot: you bump into the people you’d otherwise have to engineer a way to meet.

2:00 PM. Screen-share with my first (potential) user, a keynote speaker and stress physiologist. We walk through her v2 launch funnel. Cleaner, simpler, her edits baked in. She shows up with the good kind of questions: two offers at once, or back-to-back? How do I keep the waitlist crowd off the generic push? Should there be something for the people who don’t buy? Her message after we hang up: “copy all ready....thank you!!!! LFG.”

3:00 PM. In person with a VC Firm. Two hours in a room with both investors, the whole company on the table. I walked in with one version of Milkcrate and walked out with a sharper one.

We killed the line I’ve been leaning on — “too many tools.” That’s the symptom. The real pain is that none of the tools drives sales.

However, this feels more like a side hustle than a real business. Need to go back to the drawing board. I want to build something I can get behind.

What you can steal

Take the expensive version of yourself off the table before the other person has to.

In today’s fractional pitch, I wrote, in plain words, that I don’t think it’s justified to pay me a full salary at this stage. That isn’t modesty. It’s a reframe. The question stops being “can we afford him?” and becomes “is this the fastest path to Series B?” Name the costly option, remove it yourself, and you usually get the next conversation. Works in a sales seat. Works in a pitch. Works anywhere you’re asking someone to trust you with something that matters.

Until tomorrow,

Foley

I gave notice five weeks ago, and I still can’t give a clean answer to the question that everyone asks.

Why would you leave that?

I had the title. I had the comp, which I won’t write down here, but it was the kind of number that quietly reorganizes your family’s life around it. I was good at the job. Nobody pushed me. There was no blowup, no betrayal, no story you could tell at a dinner party that would make the decision seem brave or obvious.

That’s the part that’s hard to sit with.

If something had gone wrong, leaving would feel like a reaction to a bad situation. Like I was objectively making the right call and one I could easily explain away to recruiters, family members, and former peers.

Instead, I left behind a role I was good at, a team I cherished, and enviable hours. And now, some mornings, that choice feels less like bravery and more like I’m trying to fix something that doesn’t need fixing.

The truest version I can give: I could see the next two years before they happened. And I just couldn’t do it anymore.

Same motion: run faster, chase bigger numbers, pour more of yourself into something that was someone else’s to keep.

And somewhere in the last year “I’m fine” turned into a thing I was saying instead of feeling that was true. I don’t have a more profound reason than that. I’m a little embarrassed it isn’t more profound. But I’m learning to accept that the desire to live authentically is a good enough reason, even if it’s not a banger LinkedIn headline.

The night before I decided to resign, I sat in the car in the driveway for longer than I want to admit, running the math one more time.

How many months of runway? What happens to that math if nothing works? Run the Monte Carlo analysis. Do the back-of-the-envelope math if everything falls apart.

Am I ruining my family's future? Will I lose out on a future of status and success?

Ultimately, I realized that regardless of the math or my account balance, it would never fully eliminate the anxiety of stepping off the train.

People keep telling me that I’ll figure it out, that I can always get another job, and that even if I fail, the experience will be marketable to a future employer.

And I want to believe it. Some days I do. Some days it sounds like the thing you tell yourself after you’ve already jumped, to make the jump feel less catastrophic.

I spent most of my career striving for growth, taking a company from something to something bigger. That’s the whole reason I think I can do this, and also the reason I know exactly how often “this is going to work” turns out to be wrong.

I’m going to write this down as it happens, before I know how it ends, because I don’t trust the version of this story I’d tell later if it works out. That version is always cleaner than the truth.

So this is the truth right now. I left, on purpose, for reasons I can only half-explain, and I’m not sure if this story will have a happy ending.

What today actually looked like

• 10:00 AM — Worked a cybersecurity booth at an event with a Fractional client. I wrote the post-event outreach for everyone who stopped by and asked about a free external attack-surface assessment, loaded it into an Apollo sequence, and set it to fire tomorrow at 10

• 12:00 PM — Lunch with my former Exec coach. Turned into a referral for a fractional opportunity with one of his former business partners.

• 2:00 PM — Accelerator discovery call. 25 minutes with Refinery Ventures’ X15 program.

• 4:00 PM - Co-created a workflow for Milkcrate with a $1m/year speaker. Could be a first paying customer, but the early work is pretty bad. More to do here.

The pipeline, in numbers

• Sent a fractional CRO pitch to a founder at a Series A company. My actual line: “I don’t believe it’s justified to pay me $xxxk annually, but I can provide significant value to help you reach Series B in one day a week.”

• Locked an intro call with the CRO at [Local Series B company] for Monday.

• A partnership thread at [xxx] moved forward — NDA signed, two more intros lined up.

• A new referral request landed for a Friday call; Sourced from lunch.

The idea I can’t stop circling

Buried in seven notes-to-self I fired off this morning was the one that matters: focus Milkcrate first on the work these businesses already pay outsiders to do and feel nothing about losing. Ad management, website building, content, lead gen. Attack the outsourced, unloved work first. That’s the wedge.

What you can steal from today

If you’re building too, name the objection before the buyer can.

My booth follow-up converts because it removes every reason to say no. The fractional pitch lands the same way: I put the $xxxk salary on the table myself, then took it off. You don’t need to pay me that yet; you need the system built.

Take the expensive thing off the table, and you get the meeting.

Signal of the day

Rawmilk.io is live. Custom domain confirmed. Blog block on the calendar. Topic list written this morning. The whole machine is built and pointed at the runway.

Which leaves exactly one variable: whether I show up and write the post every single day.

Starting now.

Foley

A few people have asked what I'm swinging for now that I’ve left the fast-paced VC CRO track fueled by gasoline and anxiety. Honestly, I’m not entirely sure, but it probably involves starting my own venture. Whether that’s a business, consulting practice, or something else.

Since quitting my job four weeks ago, I’ve explored several product ideas (here and here) and spent a lot of time researching how to leverage my experience building sales teams to start my own consulting or fractional business.

The latter are often called expert-led businesses. Identify your unique skills and find a niche where you can make a greater impact than others. Begin sharing your expertise tailored to that specific audience. Grow your own email list to maintain direct contact, regardless of platform changes. Engage your audience by asking about their main pain points or bottlenecks. Use their feedback to develop relevant content and future products. Etc. Etc.

This is a cool tool to help you figure out your “expertise” and niche. And this is a good post about growing an audience on LinkedIn. Both were helpful tools, but neither ultimately helped me figure out what to do and when to take certain actions that could actually translate into income.

In addition, I have conducted outbound outreach to understand what resonates with my future customers (experts and CEOs). See two examples below.

Fractional VP Outbound

Hey [Name ] — As VP of Sales at Flock, I built the mid-market business from the ground up, scaling it from $0 to $45M in ARR in under eight quarters (>100% attainment for eight consecutive quarters).

Then I took the playbook to Edia (Series A Felicis backed), hired 7 reps, 2 managers, and ramped up one into the VP role while growing revenue from $xm to $ym in 2 quarters and driving operational rigor that created predictability for the CEO

Do you have 15 minutes tomorrow or Wednesday to see what a 90-day engagement could look like?

Best,

Ben

benjaminjfoley.com

Product Validation Outbound

To date, using the outbound approach, I’ve had 10+ product validation calls on my product ideas and landed a few consulting gigs. However, I’ve been distracted by interviewing for several jobs simultaneously. I plan to be fully focused on building my own income to support my family.

The clearest, shortest path is through fractional/consulting work, so that is where I am initially focused. This is the first time I’ve done this, so I am going to share all the lessons, pitfalls, and wins with you so that you can do the same.

Ultimately, I only have three requirements for what I do next:

1/ I need to build

2/ I need to be creative

3/ It must be local

Outside of that, I am pursuing any “green light” that comes my way, as Matthew McConaughey would say, hoping to find a path to sustaining my life without needing a full-time job.

PS: If you're also considering doing your “own thing,” what is the biggest obstacle keeping you from trying?

-Ben

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Team - it’s been a few weeks since my last post.

Since I started writing again, I’ve changed this blog’s name three times and reconsidered what I should write about more than a dozen times.

to be frank. i was terrified to share the journey. i was worried i’d lose out on opportunities. i was afraid to let go truly. I had no idea what decision to make or what direction to choose.

i still don’t.

But for the first time in my professional life, two things are true: 1/ I’m unemployed, and 2/ I'm not in any interview processes.

The anxiety spikes just writing that.

what will they think? will they think i lost my mind? lost my edge? worse?

I’ve worked at 9 companies and had 14 different roles in 11 years since graduating. I’ve received well over 30 job offers. Getting jobs was my way of propping myself up and lowering my anxiety because if I had something on deck, I could fail/leave/screw up and have a backup plan.

For the first time, I have no backup plan. And in reality, I don’t even have a primary plan. And if you know me, you know what that is likely doing to me (cough, cough).

When I left my job as SVP of Sales at a high-growth startup based in the Bay Area on April 28th, I was already in 5 interview cycles. I ended up getting 4 of the jobs. I turned them all down.

None felt right, and for the first time, I listened to myself.

But it was so freaking hard. Still is.

My anxiety is higher than it has been in a long time. My brain is searching for an answer, and most moments I try to find one, but I’m getting slightly better at not doing that.

I feel like a significant part of me is dying and is desperately screaming for help.

Since leaving my job, I have had 83 meetings with execs and founders in Indianapolis and on the coasts. My goal was 30. To say I’m compulsive would be an understatement.

I thought that by having a ton of conversations, I’d learn what my passion was, but that hasn’t been the case.

Don’t get me wrong, I’ve learned a lot and a lot of really interesting pathways have appeared, but I kept running back to the status of a job to soothe my anxiety about truly, once and for all, swinging for the f**king fences.

My whole life, I’ve been bunting. Little hits here and there to get on base. It’s kept the game alive, but deep down, I’ve always known I’d never feel authentic without stepping up to the plate and ripping it.

While I have had to pull myself, feet dragging, to the base. I’m here.

Will I swing the bat? I’m not sure, but I plan to document the journey.

1 post a day. Raw. Unfiltered musings on going from a high-status VP of Sales role at one of the top companies in the world to a 34 (soon to be 35) year old, fumbling my way to a more authentic way of living.

If that’s not for you, I get it. Feel free to unsubscribe. No hard feelings at all.

But if you are someone who may also feel that there is something deeper inside you that you’re not sure how to access, I’d love for you to join me.

Share

Not at the end, when I brag about getting through, but from the beginning.

And if you think anyone else might be curious about the journey from high status to something more authentic, please share this with them below.

As I always used to tell my sales teams, you build something great brick by brick.

I’ve never had to lay the first brick. Here goes nothing.

with gratitude,

foley

Wars are not won by evacuations.” — George Marshall, 1940

Exclaimed General George Marshall to Winston Churchill at the lowest moment of the Allied war effort, just after Dunkirk had happened.

330,000 British troops were pulled off the beaches of France, and they were celebrated at home as a miracle, but Marshall saw it for what it meant strategically, a retreat dressed up as a victory.

Marshall understood something Churchill kept resisting: you do not win wars by surviving them. You win wars by concentrating overwhelming force on the one front that ends them.

He would spend the next four years fighting for that principle in every Allied strategy session, and the argument he won is the reason you’re reading this in English.

Who was George Marshall?

If the name doesn’t stop you the way Eisenhower or Patton does, that’s by design.

George Catlett Marshall was the U.S. Army Chief of Staff from 1939 to 1945. He was the architect of the largest military force ever assembled. He built it from 189,000 soldiers to over eight million. He selected the generals who led it, designed the strategy that guided it, and held the Allied coalition together when it threatened to fracture.

Winston Churchill called him “the greatest man he had ever met.”

After the war, Marshall served as Secretary of State and designed the Marshall Plan. He is the only professional soldier in history to receive the Nobel Peace Prize.

He is not a household name to many. He spent his entire career making sure the credit went to someone else.That, too, was part of the principle.

In his essential biography George Marshall: Defender of the Republic, David Roll traces the through-line of Marshall’s life and leadership. He is a man whose defining conviction was that the greatest danger to any fighting force isn’t the enemy in front of you. It’s the dispersion of your own energy across too many fronts.

The greatest danger to any fighting force isn’t the enemy in front of you. It’s the dispersion of your own energy across too many fronts.

The argument he kept losing

From 1941 through 1944, Marshall fought the same strategic battle on repeat, to no avail. Churchill wanted flexibility.

North Africa. Italy. The Aegean. Anywhere the Allies could probe and pressure without committing fully.

Churchill’s instinct was to keep forces moving, maintain flexibility, and avoid the danger of a single decisive battle that could lose the war. However, the issue with this approach, whether in war or business, is that without strategic focus and commitment, you might not lose, but you're unlikely to win.

For Marshall, the objective was to win the war, not to extend the struggle.

“Marshall and most military strategists at the time regarded as an essential condition of success in war — concentration of effort on the decisive front.”

He lost the argument more than once. North Africa happened. Italy happened. Each time, the decisive front got delayed. And each time it got delayed, the war lasted longer.

When the Allies fully and decisively committed to Operation Overlord in June 1944, the European war concluded within a year. Although the principle was eventually secured, it took three years of Marshall's persistent refusal to abandon it before it was achieved.

What he learned from Pershing

The conviction didn’t come from nowhere.

Marshall had served under General Pershing in WWI and absorbed a lesson that shaped everything that followed. Pershing had fought the same political battle against allied commanders who wanted American troops parceled out across French and British units rather than concentrated as an independent force.

Pershing resisted. Marshall watched. And what Marshall took from it wasn’t just tactical, it was philosophical.

“From Pershing, Marshall also learned that in an allied coalition one should strive to minimize the dispersion of forces to other fronts and instead concentrate overwhelming power against the enemy.”

Minimize dispersion. Concentrate overwhelming power.

He carried that sentence into every room he entered for the rest of his career.

The cost of being right

The hardest part of Marshall’s story isn’t that he fought for concentration. It’s what it cost him personally.

He had advocated for the Normandy invasion for nearly two years. He believed in it completely. Pershing had recommended him for a star after WWI. He had spent thirty-seven years preparing for exactly this kind of command.

And when Roosevelt asked him whether he wanted to lead Operation Overlord — the invasion he had designed, argued for, and refused to abandon — Marshall declined to express a preference.

He told the president to make whatever decision was best for the country, and not to consider his feelings.

The command went to Eisenhower.

“It required extraordinary moral discipline — strength of character — for Marshall to refrain from asking FDR for the command when he knew it would be granted.”

He never complained. Never made his feelings known. The principle mattered more than the recognition.

That, too, is part of what concentration requires. You don’t get to fight on every front.

How does this essay relate to growing durable businesses?

I’ve spent the better part of ten years inside GTM orgs at every stage of growth.

The recurring issue I observe isn’t related to poor reps, weak pipelines, or incorrect CRM choices. Instead, it's dispersion: pursuing three ICPs simultaneously, juggling five incomplete initiatives, and distributing energy across numerous urgent opportunities. This scatter prevents any one effort from gaining the momentum necessary to close successfully.

Marshall would recognize it immediately.

The founders and CEOs I collaborate with aren’t failing due to a lack of effort. Their setbacks stem from not choosing the right front to focus on.

That’s what this newsletter is for.

Join 2,100 founders and operators who read the Decisive Front every Saturday. One short essay on concentrating overwhelming force on the one front that can drive durable growth, in business and life.

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This is The Decisive Front.

Welcome.

— Ben

Roy Williams was struck afterward by how little it took. One conversation with Jordan, and no one would ever outwork him again.

Early in his career at UNC, Jordan was seen as too casual and abrasive. His effort didn’t match his goals. He wanted to be the best, but his actions showed his immaturity.

Williams, then the assistant coach, challenged him on it. Jordan said he was trying as hard as everyone else. Williams told him that if he wanted to accomplish great things, trying as hard as everyone else wasn’t enough. He had to work that much harder than everyone else.

It’s advice we’ve all heard. What’s rare is what Jordan did with it.

Reflecting on it later, Jordan said: “My greatest skill was being teachable… I was like a sponge… even if I thought my coaches were wrong, I tried to listen.”

Most people believe Jordan’s drive was innate; something he was simply born with. The reality is that without a great coach in Williams, and without Jordan’s willingness to listen and adapt, he might have been successful, but nothing close to what he became.

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Recently, I came back to Roland Lazenby’s Michael Jordan: The Life. This book is arguably one of the best written about MJ, thanks to its personal insights into his upbringing. It shows how his father's fear imposed on the family fueled his relentless ambition and drive. Notably, one sentence stood out more than others, resonating so deeply that it has been identified as the core influence behind the famously competitive athlete.

From Lazenby:

The same teachability that made Jordan great is also what made the anger permanent. He was a sponge, but a sponge soaks up whatever it’s sitting in. He absorbed the coaching and the resentment, and he never wrung either one out.

I’ve been thinking about this a lot in my own life. Not only am I trying to be much more cautious with the words I use with my boys, but also working to uncover the beliefs or resentments that may be unconsciously driving my life.

What we absorb, absorbs us.

Jordan’s story ended with him as the greatest of all time; someone people around the world look to as an inspiration of dedication, perseverance, and craft. But what most people don’t see is isolation, the anger, and the negativity that still drive him today.

If you don’t believe me, watch his Hall of Fame speech and tell me that’s a happy man. I don’t know him. But to me, he looks like someone still trying to prove the world wrong, decades after he won.

So I have to ask myself the same question about my own ambition.

I have driven myself so hard to succeed in my professional life, but I have never stopped long enough to ask myself why I want to succeed in the first place.

When you look in the mirror, do you see someone with a genuine passion for your craft? Or do you see someone eager to show other people that you matter, that you are important, that you are worth their time?

For me, the answers are hard to face, but I am working on facing them, writing them down, exposing the flaws in my pyche that have been unconsciously ruling my mind for far too long.

I don’t want to wake up at 50 as a successful, angry, lonely man. Surrounded by everything I acquired, and none of what I actually wanted.

I won’t pretend I’m not ambitious. I am. I’m building something, and I want it to be excellent. The question isn’t whether to want greatness; it’s whether the work itself can be the reward rather than needing the outcome or approval of others.

I will never reach greatness the way Jordan did. I’ll never be widely known around the world. But my new north star is to be in the “Hall of Fame” in the minds of the people I care about the most. To have them be able to say that I lived my life, authentically, the way only I could.

It’s a high bar, but it’s worth chasing, don’t you think?

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Hey there!

If you’re reading this, you probably have a job you’re not psyched about and an idea rattling around in your head that you don’t know what to do with. I’ve been there.

I’m going to walk you through exactly how I built my own app, Chalk, in two weeks.

What worked, what was a massive waste of time, and the specific tools and templates I used. You can take all of it. This is what I wish someone had handed me before I started.

A little context on who I am and why I built this

I spent years in B2B sales. Eventually helped scale a company from $30M to $450M in ARR. I hired and onboarded 80+ reps. I ran enablement. I sat in on hundreds of calls. And the thing that kept bugging me was simple: sales training is broken.

We’d fly a team to a resort, run a two-day offsite, spend $500K on a methodology firm, get everyone hyped — and then watch reps go right back to doing exactly what they were doing before. Nothing stuck. Not because the content was bad. Because that’s just not how humans learn.

I knew what actually works. Short daily practice. Repetition. Feedback loops. Accountability. That’s it. Duolingo figured it out for language learning. Nobody had done it for sales. So I built Chalk.

Chalk is a gamified B2B sales training platform. Reps do 5-minute daily drills. AI analyzes their gaps and gives each person a personalized path. Managers get a leaderboard and real visibility into who actually knows their stuff.

The mistake I made. Don’t do this!

I had the idea. I thought it was good. I started building. I spent two weeks putting together the actual product — the logic, the UI, the drill flow, all of it. I was proud of it.

Then I showed it to people. Nobody would buy it.

Do not build anything until someone has told you they will pay for it. Not that they like it. Not that it’s a cool idea. That they will actually pay.

This is not a new lesson. Every startup book tells you this. Every founder podcast tells you this. I still did it wrong. You probably will too if you’re not careful. So let me be clear: your first job is not to build. Your first job is to find people who will pay.

Two things I should have done before touching any product tool:

1/ Build an audience of people who might care about the problem I was solving

2/ Talk to them and ask if they’d buy it — before building a single thing

Everything below is the order I wish I’d done it in.

Step 1: Build an audience before you build a product

This is the most boring advice and also the most important. You need to build an audience of people who share the problem you’re trying to solve. Not friends. Not family. Not people who will be nice to you. People who actually live in the problem every day.

For me that meant VPs of Sales, team leads, revenue leaders at Series A through C companies. Those are my people. I needed to find them and start talking before I built anything.

The tool: Substack

Substack is free. It takes 20 minutes to set up. And it is the single best way to start building an audience of people who care about what you’re thinking about. You don’t need to be a writer. You just need to be honest and useful.

Here’s what I’d do if I were starting today:

1. Pick one specific problem your audience deals with. Not “sales is hard.” Something specific — like why reps forget everything from training within 30 days.

2. Write a post about it. 400–600 words. Share what you actually know. Don’t try to sound smart. Just be direct and useful.

3. Post it. Share it in two or three places where your people hang out — LinkedIn, a Slack group, a community forum.

4. Do that every week. Not every day. Every week.

5. After 4–6 posts you will have a list of people who actually care about the problem. Those are your first conversations.

The real goal of the newsletter isn’t to become a content creator. It’s to build a list of warm contacts who already know you understand their problem. When you message them later and ask if they’d pay for a solution, it’s not cold outreach — it’s a conversation with someone who already trusts you a little.

Step 2: Do discovery outreach before you build anything

Once you have even a small list (20 will do), start talking to them. Not pitching. Not selling. Asking. This is called customer discovery, and most people skip it or do it badly.

The goal is not to validate your idea. The goal is to understand the problem deeply enough that your solution actually solves something real.

The outreach template

Adam Robinson from Retention.com talks about this framework in his content and it’s the cleanest outreach approach I’ve found. The structure is simple: be a real person, name the problem, ask for time. No pitch. No deck. No “I’d love to pick your brain.”

Here’s the message:

Hey [First Name],

I’ve been following your work at [Company] — congrats on [specific recent thing: a hire, a post, a funding round, a launch].

I’m working on something in the [sales enablement / sales training] space and I’m trying to talk to as many people as I can who actually run sales teams before I build anything.

Not looking to pitch you. Just trying to understand if the problem I’m seeing is real for teams like yours. Would you be open to a 20-minute call this week?

[Your name]

That’s it. It’s short. It’s honest. It doesn’t pretend. And it works because nobody is asking people to share their real problems — everyone else is pitching immediately.

What to ask on the call

You have 20 minutes. Ask these 5 questions. These come from Adam Robinson’s great YouTube channel on building a SaaS company in 2026.

• Do you understand the problem I am try to solve?

• Do you have the problem I am trying to solve?

• How are you solving this today?

• What else would this solution have to have in order for you to pay for it?

Near the end, ask one more question: “If I built something that solved exactly what you described, would you pay for it?”

This is THE key question. Not if they are interested. Not if they think it is cool. Not even if they want to use it.

No, will they pay you for it TODAY if you could get it to them.

Do this with 15–20 people before you write a single line of code or touch any design tool. The thing I built that nobody wanted? I talked to four people and heard mostly positive reactions. Four people is not a signal. Fifteen honest conversations is a signal.

Step 3: Now you can actually build — here’s how I did it fast

Okay. You’ve talked to enough people. You’ve heard the same pain point in enough different ways. You know what you’re building and you know someone will pay for it. Now you can build.

Here’s the stack I used. All of it is fast, cheap, and doesn’t require you to be a developer.

Polsia — [my referral link here] This is the main tool I used to actually build the product. It handles the app infrastructure, hosting, and the backend without you needing to write code from scratch. Genuinely the thing that made this possible on the timeline I had.

Claude Design — I used this to build all the design elements, generate copy, think through product logic, and move fast on things that would have normally taken me days. Claude design is so killer. It helps you build fonts, brand colors, even full UI wireframes. Try this out.

Substack — already set up in Step 1 It becomes your ongoing distribution channel as you build. Every time you ship something new, your audience is there to see it.

LinkedIn — free, already where your customers are. Post about what you’re building, what you’re learning, and what surprised you. People root for founders who are transparent about the journey.

The one rule I kept for what to build first

I did not try to build everything. I picked the one thing that would prove the concept and built only that.

For Chalk, that was the drill experience. If a rep couldn’t sit down, open the app, do a five-minute drill, and walk away feeling like they actually learned something — nothing else mattered. The gamification, the leaderboards, the manager dashboards — all real, all in the product — but they came after I knew the core experience worked.

Your MVP is working when a stranger can use it without you explaining anything and they come back on their own the next day. Not “it has all the features.” Not “it looks great.” They came back without being asked.

Step 4: What I built and why it’s different

Every VP of Sales I talked to said some version of the same thing: we spend a lot of money on training and we can’t tell if it’s working. No visibility. They didn’t know which reps had actually internalized the methodology and which ones were faking it in pipeline reviews. They knew results — but by the time those numbers show up, it’s too late to fix anything.

Chalk works like this. Every day, a rep opens the app and does a 5-minute drill. It’s tied to the actual stage of the sales process they’re in — pre-call prep, discovery, champion building, demo delivery, post-demo follow through.

The AI analyzes their responses over time and figures out where their actual gaps are. Not where they think their gaps are. Where they actually break down. Then it builds them a personalized path. One rep is doing advanced discovery drills because they’re solid on the basics. Another rep is back to fundamentals because the AI caught that they don’t actually know how to find a real champion.

Managers log in and see a leaderboard — not of quota attainment, but of skill development. Who’s practicing. Who’s improving. Where the gaps are — before those gaps show up as lost deals.

The research behind it

There’s a 40-year-old study called Bloom’s 2 Sigma problem. Benjamin Bloom found that students who got one-on-one tutoring performed two standard deviations better than students in a regular classroom. Two standard deviations. The difference between an average student and a top 2% performer — just from the format of the learning, not the quality of the content.

You can’t give every sales rep a personal coach. It doesn’t scale. What you can do is use AI to deliver that kind of individualized, adaptive practice at scale. That’s what Chalk is.

Step 5: How I thought about pricing

I made the free tier permanent on purpose.

The best salespeople are always trying to get better on their own. They don’t wait for their company to buy them training. If I can get a rep using Chalk on their own and they love it, eventually their manager sees the leaderboard and wonders what it is. That’s how the team plan gets sold — not from me cold-calling VPs, but from a rep inside the company becoming a champion for the product.

That’s the flywheel.

Free: 1 drill per day, forever. No credit card. Unlimited drills, full AI gap analysis, personalized path.

What I’d do differently

• Talk to 20 people before building anything. Not 4. Not 8. 20.

• Start the Substack six weeks before I started building so I had a real audience when it launched.

• Nail the outreach message earlier. The template above would have saved me a lot of awkward intros.

• Build even less at first. The first version had too much. I should have launched with just the drill experience and gotten that right.

Okay. Go build something.

You don’t need to be a developer. You don’t need funding. You don’t need permission. You need a real problem, a list of 20 people who have that problem, and the willingness to have honest conversations before you touch any tools.

The tools are easy now. What used to take a team and six months takes one person and six weeks if you use the right stack. The hard part — the part that actually matters — is finding out what’s true before you build.

If you work in sales and want to try what I built, go here. Free. Always will be. No credit card.

[Link to Chalk]

Five minutes a day. Real skill development. Built for people who actually want to get better.

Over the past decade, I’ve received more than 30 job offers. I’m not especially proud of that, because if I’m being honest, some of it probably stems from a deep need for external validation, but I digress...

I’ve never applied through a job board. And until my most recent position, I’d never spoken with a recruiter. Every opportunity followed the same pattern, and I’ve never written it down until now.

Recently, I’ve been talking with many people who are genuinely struggling to find work. That has never been a challenge for me. Luck and privilege are real, and I’m grateful for both.

But I also believe there’s a process that actually works, and if you’re searching right now, I hope this helps increase your odds of finding the next thing.

Step 1: Start with accounts, not job boards

The first thing I do when I’m looking for a job is to build a list of companies I’d actually want to work for. Not a list of open roles. Not a LinkedIn search. A list of companies that fit my criteria for something I’d be excited to do next.

The best jobs are never posted. They get created for people who show up before there’s a job description.

The question isn’t “what’s open?” The question is “who would I want to work for?” Get that list. Then go do outbound.

Find people inside those companies, in the department you’d want to work in, and reach out to them. Not to ask for a job. To learn.

Come curious, with real questions. You’re doing discovery: what do they actually do, what does the company look like from the inside, what do they care about?

Here’s what most people miss about this: it’s not just a tactic to get in the door. Every one of these conversations compounds. That person now knows you. They’ve seen how you think. They can refer you, introduce you, and give you inside intel during the interview process. A decade from now, when you’re both somewhere different, that relationship is still there.

Currently, I’m holding 30 of these meetings while searching for my next opportunity. After just one week, my calendar is already packed with referrals from those initial meetings. Yours can be too, with the right messaging.

After these meetings, you’ll understand the landscape: who’s building, who’s coasting, and what kind of work you actually want to do.

You’ll leave some of those calls with more energy than you walked in with. Others you’ll leave thinking, “absolutely not.” That signal is gold.

Run it like a sales process.

Confirm the meeting the day before. Follow up within 24 hours with what you took away from the conversation.

And before you leave every call, ask: “Who are one or two other people you think I should know?”

Nine times out of ten, they’ll make the intro. Your network multiplies whether you get a job from that person or not.

Step 2: Stand out before the interview starts

Let’s say there’s an open role or a first meeting on the calendar. Your job is to prep like you mean it.

Find two or three people at the company on LinkedIn, not the hiring manager, just people who work there, and message them directly. Tell them you’re interviewing for the role and ask for 10 minutes to hear about their experience there.

Nobody does this.

I’ve been a VP of Sales for 3 years. I can count on one hand the number of candidates who reached out to me directly about an open role on my team. Every single time it happened, I gave them a first interview. Every time.

You can also reach out cold to the person doing the hiring. Keep it sharp and specific. Here are two examples from different career stages.

The first is from a place where the track record speaks for itself:

Hey [Name], at [Company] I built our mid-market business from the ground up, scaling it from $0 to $45M ARR in under eight quarters, hiring 60+ reps, and putting in place the culture and operating rigor that made it repeatable. I’m interested in joining the GTM leadership team at [your company] to help grow another rocket ship. Thanks for considering the outreach. Ben

The second is from earlier in my career, before I had numbers to lead with. Here I leaned on genuine curiosity and a specific reason I cared:

Dan, my name is Benjamin Foley. I came across your profile after doing research on Sigstr. I hope you don’t mind me reaching out cold. I’ve spent the last two years building and selling an e-commerce business I started at IU. Starting my own thing taught me a lot about attracting and retaining customers, but after two years working alone, I had a real desire to build something bigger with a team of talented people. My interest in Sigstr is specific: I’ve seen the value of a great email signature CTA firsthand growing a blog that just passed 7,000 subscribers. I believe Sigstr is poised to execute on a huge opportunity and I’d love to add value to your growth. If you’re willing to connect, I’d love to grab a coffee and learn more about your vision for the company. With gratitude, Benjamin Foley.

Different career stage, same idea. Do the work, be specific, make it about them.

Step 3: Nail the first call

Here’s the thing nobody tells you about first calls: your job is not to talk about yourself.

I know that sounds backward. But when I get on a first call, I have a list of questions I want to ask. I open like this:

“Hey [Name], I’m really excited to learn more. I have a bunch of questions I’d love to ask. I’m sure you have questions too, so we can start wherever you want.”

Nine times out of ten, they say, “What questions do you have?” Now I’m running the meeting.

They talk. They tell me what they actually care about, which is almost never what the job description says. They like me more because people like those who are curious and let them talk about themselves and their company. And I’m learning exactly what I need to know to decide if I want this job and how to get it.

Confirm pain. Build the champion. Close with the next step before you hang up.

One more thing: send an agenda email 24 hours before the call. Here’s an example of what that looks like:

[Name], I’m looking forward to connecting. I’ve spent some time digging into [company’s] mission and customer stories and it’s clear you’re not just solving a compliance problem, you’re redefining how scale and trust coexist in regulated markets. I also really enjoyed your conversation on [podcast] and your piece on [topic].

To make sure we cover what’s most useful to you, here’s a loose outline I can tailor based on your priorities:

• My background: building high-rigor, high-growth sales orgs in complex environments

• Your ideal future state and success metrics at 90, 180, and 365 days

• Enterprise traction, expansion opportunities, and current limiters

• How you think about GTM structure, methodology, and enablement

Looking forward to the conversation. With gratitude, Ben

Nobody does this either. It takes 15 minutes, and it always lands.

Step 4: The 24-hour follow-up

Within 24 hours of every conversation, send a follow-up. Not a transcript. Not “great chatting.” Something that shows you were actually listening and adds something back.

Here’s what that looks like in practice:

[Name], thanks for the time today. I came away more excited about the role. The territory setup, the way you think about running the business, the anchor account focus, the 90-day ramp bar, the pipeline metrics. That’s a structure I understand and know how to operate in. I know the concern around recent IC execution is real, and I don’t want to paper over it. What I’d say is this: I’ve spent the last two years coaching 60+ reps through exactly this motion. I know what good looks like, and I’m motivated to close that gap in the first 90 days. Looking forward to speaking with [next person]. Ben

Do the work

Then go further. Based on what you heard on the call, whether it was a problem they mentioned or a challenge they’re stuck on, build something.

A framework, a short plan, a model. Send it over with a note: “Probably way off base, but based on what I heard, I put together some quick thoughts on how I’d approach this.”

With Claude/ChatGPT and your call notes, this should take you all of 1 hour, but you will move yourself into the top 1% of candidates. Not because you’re the most qualified, but because you showed them what it’s like to work with you before they’ve hired you.

The meta-point

Run this whole thing like a sales process. Research before every meeting. Send the agenda the day before. Follow up within 24 hours. Always close with a next step. Ask for two introductions on every call before you leave. Build champions. Go out, learn, iterate, go out again.

Most people are too lazy to do this. That’s the opportunity.

The best jobs are never posted. They get created for people who show up as if they already work there.