5 things starting over has taught me

Day 7 of building in public, and the journey to here.

Photo by Daniel Sinoca on Unsplash

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