Read This Before You Leave Your Corporate Job To Launch A Startup
The Entrepreneur Exodus (the corporate executives leaving large companies to launch startups) is very real and very hard.
It’s real because over the past three years a record 80 million Americans have left their jobs and launched 18 million new businesses, an all time high. 5.5 million of these businesses are ‘high-propensity’ according to the Bureau of Labor Statistics, meaning they are well-funded and have more than two full-time employees. 39% of Unicorn startups (startups valued greater than $1billion) were founded by people who left leadership positions in the Fortune 500.
It’s hard because the conventional startup playbook was written for a 22 year old Stanford dropout, not a 45-year old with kids, a mortgage, a 401k, and deep understanding of a niche multi-billion-dollar problem.
For this article I spoke to three members of Punks & Pinstripes, a vetted membership community for Exodus Entrepreneurs. Where’s what they said.
Exodus Entrepreneurs at a Punks & Pinstripes Party in Brooklyn
I. There’s a Right Reason to Switch to Startups (and a Wrong Reason)
The right reason is that you know you can have a bigger impact starting from scratch than you could in a large, entrenched company. “At a certain point in my career I realized that impact was more important to me than positional status. I’d be lying if I said that was an easy realization, but I started to recognize companies that talk about transformation rarely have the enterprise-wide patience and investment thesis to make it happen. Sustaining the status quo in an industry ‘sea of sameness’ suppressed my value and drive - the fire that myself and my teams ignite in spades to achieve progress, transformative growth, and market success.”
Nyla Beth Gawel
Nyla Beth Gawel, former SVP of Corporate Strategy in the public sector tech industry and current CEO, NBG Consulting
Rama Penta
Most companies, especially companies in mature industries, are primarily focused on sustaining legacy businesses. They usually innovate on the periphery to keep pace, but rarely with the intention of transforming themselves or their industry. It’s the right move to join the Entrepreneur Exodus when you can (1) no longer settle for the innovation constraints of a huge company seeking to eek by and when you (2) have a clear vision of the broader impact you can have, and knowing you’d regret not trying.
“What would it take for me to really get excited to get out of bed each morning?” was what Rama Penta asked himself before leaving his job as director of technical innovation at Bayer. He knew he needed to launch a new venture and leave the stability of Bayer, and Big Pharma to feel that excitement again.
Don’t leave if you merely dislike your company, or your boss, or you think you can make more money elsewhere. If that’s the case, move to another corporate job in another company; don’t make the move to entrepreneurship. You won’t be able to persevere through startup adversity without a big, smoldering fire in the belly.
2. Be an Alumni Entrepreneur Not a Disgruntled Disruptor
Your best possible outcome is that whatever you do next, your former employer will be your first investor, your first customer, or both.
This is especially tricky if some entitled narcissist a$$hole screamed at you, stole credit for your work, sabotaged you, or gaslighted you for taking time off to attend your uncle’s funeral. This is especially true if you’re a woman or minority, and there is a thin haze of sexism, racism, or xenophobia that permeates every interaction.
For one member of Punks & Pinstripes, not burning a bridge was incredibly hard. She was nine months pregnant working as an SVP for a huge, publicly traded company, leading due diligence on a potential acquisition. When she identified a red flag in the potential target, her boss muted the phone and screamed at her to “SHUT THE F*** UP!” They acquired the company despite her reservations, and wrote the $90mn investment down to $1 three years later.
And she remained friends with the leadership team. They are one of her first phone calls when she’s looking for a potential acquirer, partner, or customer. If you can’t demonstrate that level of emotional composure, this might not be the right move.
3. 40 Meetings in 40 Days
A few things will happen to you during those meetings.
You will recalibrate from corporate to startup - The first thing I did when I left my job at Bloomberg was invest $2000 in SCRUM certification. Only to be told by a major VC that no one outside of huge companies with boring products cares. I should have met with the VC before I spent the $2000.
You will find support - people who’ve gone through what you’re going through generally want to help. They will open their network to you. They will share what worked for them. And they will shut up and listen when you talk about the hard conversation you’re having with your spouse about money, or with a potential co-founder about equity, or a potential investor who says you’re too old.
You will find a client - and it won’t be the client you thought you would land. My first client was Nickelodeon, the children’s television network. I’d spent the previous decade on Wall Street. It made no sense. And yet it worked out. It was a great engagement. We still love each other and go for dinner every few months.
You will see who not to date - I met with more 29 year old, adderall-addicted, tech bros and girls than I can count. It quickly became evident that I was too old for that $hit. I quickly realized that there are lots of subscribers to Hustle Culture and I was not one of them. That was important data to collect early.
4. Find Your Voice and Speak Your Truth
The night after I handed in my resignation I was asked to introduce myself at a VC conference in NYC. When it came time for me to say a few words I just said the truth, “I’m Greg Larkin, and today I quit my job as Director of Innovation at Bloomberg.”
That simple, clear, unpolished statement was a starting point for many great relationships. Well-connected, important people wanted to know why I left? What’s next? If they could introduce me to their network? Is Wall Street disruptable?
When you’re a corporate executive, your voice becomes increasingly stage-managed by compliance people, communications people, investor relations people, etc…. You forget how to be gutsy, authentic, honest, and constructively provocative. You need to reignite your inner flame, and share it with the world. People will trust you more than anyone else if you’re able to speak your truth. You project the strength of a survivor.
5. Recognize Your Unfair Competitive Advantage
The reason that the Entrepreneur Exodus is, statistically speaking - the most successful founder demographic, is that they see billion-dollar problems that can be solved faster, smarter, and cheaper. They’ve done everything they can to solve those problems from inside a huge company and eventually realized they could make more of an impact and make more money starting from scratch on the outside. No offense, but that is a much more advantageous starting place than someone with a generic interest in AI, or blockchain, or a dating app. This is why statistically speaking the most successful founders are 45, and the average age of the founders with the largest fundraising rounds of 2023 is 52. “Exodus Entrepreneurs have a clear understanding of what it takes to scale. They’ve seen the risks, manage through them, and have navigational skills for enterprise success” says Nyla Beth Gawel.
The Entrepreneur Exodus tends to be incredibly supportive and generous to people who are leaving corporate leadership. If you’re driven to be impactful, are prepared to share your truth, and willing to invest in your community it can be an amazing second chapter of your life.
Y’all are my heroes,
Greg Larkin
Founder, CEO, Punks & Pinstripes
If you like this article, please:
Subscribe and share it.
The next opportunity to become a member of Punks & Pinstripes is Sept. 8 - 22. We only accept 25 new members during a 2-week application period every quarter, and membership is capped at 200.
