The most dangerous misinformation about #entrepreneurs is the myth of the dorm room startup. The reality is that the most successful entrepreneurs are over the age of 50, spent the first half of their career in executive leadership inside the Fortune 500, and launched a startup after they realized they were hungry for something bigger than the corporate life.

The average age of the founders with the biggest fundraising rounds of 2023 is 52 years old. If you remove OpenAI's Sam Altman (he's 38) the average age jumps to 55 years old. However, the average age of the entrepreneurs on the cover of Fast Company is 38, it's 35 on the cover of Entrepreneur Magazine, and drops again to 33 if you survey the guests of Sam Parr's podcast "My First Million."

A Boardroom Entrepreneur Has Different (unmet) Needs Than a Dorm Room Entrepreneur

I was 40 when I left my last corporate job to embark on the second entrepreneur chapter of my career. I met a lot of much younger entrepreneurs who had the bravado of someone who hadn't gotten their asses kicked yet. Founders who were perfectly nice, but had no kids, no mortgage, and had subscribed to the mythology of Hustle culture. I was once one of them, but was not that person anymore. As a boardroom founder I had a different hierarchy of needs than the dorm room founder.

The Boardroom entrepreneur's hierarchy of needs looks like this:

Belonging - "You are not alone." The boardroom entrepreneur needs to hear that a lot more. People think you're insane to walk away from the stability of executive leadership. You need a network of support which is equal parts group therapy and tactical support. It's important to have a community where you can reveal your most raw character defects and get a big hug, with zero judgment.

Impact - Over time it matters more to make a dent in the universe and solve important problems. The problems that seem worth solving evolve as you age. My time in corporate executive leadership revealed obscure $billion problems (like the inefficiency of investment banking due diligence, or the uselessness of management consultants) that I couldn't see when I was 25.

Success - How you make money and earn recognition is very different when you're over 40. When you have kids, a mortgage, and a 401k many VCs will make demands that aren't feasible (for example that you invest your savings and 401k into your startup). That's not an option at this stage in my life. And the recognition I seek out is more niche. You want to be seen as an expert in your field, rather than an influencer for everyone. Lots of KPIs seem like vanity metrics.

Practitioners > Pundits - After a while you become deeply skeptical of the advice from influencers, coaches and thought leaders. They offer advice without accountability and expertise without experience. Increasingly you find that you only trust people who’ve gone through what you're going through. You seek out survivors - not observers because their advice is rooted in deep empathy and is often fundamentally different than the conventional playbook.

This is why I created Punks & Pinstripes. It's the community I wish I had when I left corporate executive leadership for my second entrepreneur chapter. Our members are the corporate entrepreneur exodus: the boardroom startup founders who left corporate executive leadership. Everything we do is to foster the right hierarchy of needs: belonging first, then impact, then success. We’re unafraid to talk about how hard it is. We’ve experienced the anticlimactic crash that follows a big 'success' that doesn’t feed your soul. And, yes, we help each other make more money, get new jobs, and get unstuck. Our members are in the corporate C-suite, within striking distance, or left to build new ventures.

So, if you're reading this and it resonates, please find a community that gives you the belonging, impact, and success that's right for you. And if you think that community is Punks & Pinstripes, then we're waiting by the phone for your call.