Why I Stepped Away for Seven Years, and Why I'm Back

In 2018 I left LinkedIn and stepped out of public view. I didn't stop working. I kept helping founders for free, for equity, and with my own money. I'm back now because the number of people building companies has exploded, and the support around them hasn't kept up.

This is the longer version of that story: what I walked away from, what the quiet years taught me, and why I decided to stop working in the background.

Where I was in 2018

At the time, I thought I had reached the top. I had climbed the corporate ladder, led M&A for a billion-dollar company, and helped scale a bootstrapped business to the top of the Inc. 5000 list.

I'd been at it a long time. I started my first business at twelve. By 2018 that was twenty years of the grind, and most of it had been measured the way careers usually are: titles, deals, growth numbers.

So I stepped away to start a family, travel, and see what else life had to offer. You can read the fuller background on My Story.

What the quiet years looked like

Stepping away from the public part of work is not the same as stepping away from work. During those years I kept working with founders.

• I helped for free when someone needed an answer more than they needed money.
• I helped for equity when I believed in the company enough to tie my outcome to theirs.
• I invested my own money when capital was the real constraint.

Along the way I learned cap tables, venture capital, and private equity from the inside out. Not from a course, but from sitting next to founders while they made the decisions that shape a company.

Doing it without a public profile had one big advantage. Nobody was performing. The conversations were about the business, not about how anything looked.

Why working alone stopped working

The quiet model worked for a handful of founders at a time. The better it went, the more people asked for help, and I started turning people away. Not because they weren't worth it, but because there was no structure to support more of them.

That's the ceiling of doing this as one person. Your judgment doesn't scale, your calendar doesn't scale, and the founders who need help most are often the ones you never get to.

That problem is the reason Outperform Ventures exists. It's going from a silent investment vehicle to an active part of the discussion, and I'm thankful to have a partner like Rob Peabody and a great team alongside me.

10x more founders need 10x more support

There are more solopreneurs today than ever before. Having 10x more entrepreneurs is great. But we need 10x more support systems to match.

Capital is scaling fast, but real support is lagging behind. Tier 1 VCs are fighting over the same slice of AI companies, while thousands of incredible founders outside that bubble are figuring out the hardest parts alone.

Most of those founders don't need a check from me. They need the answer to one hard question, fast, from someone with no agenda. What is my company worth? Should I raise or bootstrap? What's capping my growth?

What founders outside Silicon Valley face

The founders I worked with in the quiet years rarely looked like the ones on magazine covers. Many were bootstrapped. Many were building in industries venture capital doesn't chase. Most were smart, hardworking, and stuck on a handful of decisions that would shape everything after.

• Money. Whether to raise, how much, and from whom, without a trusted person to pressure-test the answer.
• Value. What the company is really worth, and what they'd actually take home if they sold.
• Growth. What is capping the business right now, and what to fix first.
• People. Who to hire next, and when the founder needs to step out of the way.

None of those questions require a famous investor. They require experience, honesty, and time. That combination is exactly what's in short supply, and it's the gap I want to help close.

It's also why the support has to come in different forms. Some founders need a deep partner. Many just need a clear answer at the right moment, and then they're off and building.

Why I'm back in public

I see the next generation of passionate founders, and it's too exciting not to be a part of.

Being public is how the help scales past my calendar. Every article on this site is an answer I used to give one founder at a time. The free tools are the same idea: the questions I get asked most, turned into something anyone can use without a meeting.

• Articles share what I've learned, so the same lesson reaches more than one person.
• Tools answer the common questions in minutes, with no sign-up.
• Outperform Ventures goes deep with the founders where capital, time, and judgment make the biggest difference.

There's also a simpler reason. For years, the lessons I learned stayed in private conversations. Writing them down means they outlast any single meeting. A founder I'll never meet can read an article years from now and avoid a mistake I watched someone else make. That's the kind of legacy I care about: not a title, but help that keeps working after the conversation ends.

Coming back in public also holds me to a higher standard. When you share what you think, people can test it, push back, and tell you where you're wrong. That makes the thinking better, and it makes the help more useful.

What hasn't changed

The work is the same as it was in the quiet years. I grow people and businesses. What's changed is that there's now a structure and a team behind it, and a public place where anyone can take what's useful.

If you want to start reading, try the real costs of raising versus bootstrapping or Leadership & Legacy.

If you are building something ambitious, let's connect.