Want To Build A Unicorn? Be Like Bobbie.

Before Bobbie Shrivastav co-founded Docsmore and Benekiva , two of the fastest-growing enterprise tech #startups in the United States, her department’s director stood in the doorway of her North Carolina office and glared at her. “Why is your office door always locked?” he demanded to know.

Her office door was locked because she was pumping for her 3-month old daughter. She had cut her maternity leave short by a month because she was determined to complete a massive, and mission critical digital transformation project ahead of schedule. Her company was so dominated by old, white men that they had no way of categorizing her maternity correctly. So, she was marked “absent for a life event.” This was the category normally reserved for death - not birth. 

At that moment, with her boss blocking the exit she decided that she was done. Even if she was scared of what her career might be on the other side. She wasn’t simply done with her company. She was done working for any huge company. 

She was sick of her motherhood being treated like a disease by men who reminisced about their secretaries typing their memos for them while they golfed together.

She was sick of working 80-hour weeks and being treated like she was a slacker. Because she worked from home so she could balance her maternal and professional responsibilities. 

She was sick of her work being diminished because it was digital and unrecognizable to a digitally-ignorant leadership team. She was converting 48 years of a paper-based company into a modern, cutting edge user experience, and enterprise management system for a company whose margins were contracting because they were slow, inefficient, and complacent.

At that moment, with her director blocking the exit, she realized that the risks of leaving were outweighed by the risk of staying. She hustled her ass off. She sacrificed the things that were most important to her. And even though she was on track to complete a massive digital transformation project ahead of schedule and under budget she was being accused of being lazy and opportunistic by a man who confused breastfeeding for playing solitaire.

“If I don’t create a path for myself I would have been stuck in their box. And I couldn’t allow that.” is how Bobbie described her realization to me. 

Bobbie left that job and joined the Entrepreneur Exodus - the corporate executives who are leaving corporate leadership to launch new ventures later in their careers. This is increasingly the largest, and most successful founder cohort in America. By almost every metric: the size of their funding rounds, their speed to unicorn status, their ability to retain their value during a downturn, these are the most successful startup founders of our time. The founders leaving the corporate boardroom are a much better bet than the founders leaving the college dorm room. They solve multi-billion-dollar, unsexy problems that are only visible to people who spent 20 years hitting the digital and cultural limitations of legacy companies and industries. 

But despite the success of the Entrepreneur Exodus, when they decide to leave, they’re made to feel reckless, indulgent, and stupid. Because the image of a successful founder is a 25 year-old who fully subscribes to Hustle culture. Not a 40-year old Mom like Bobbie pumping for her newborn while building a startup that’s doubling in size every 12 months. The average age of the founders with the most successful funding rounds of 2023 is 53 years old. The average age of the startup founders on the cover of Fast Company is 31. 

Put differently, if you’re a corporate executive like Bobbie, it’s economically rational, sensible, and smart to tell your boss “You know what? I quit. I’m launching a startup.” when they humiliate you for pumping for your newborn daughter. The data increasingly indicates that you’d be happier and make more money if you left.  

If you’re reading this, and you’re part of the Entrepreneur Exodus, here’s what i want for you:

1. Find Your Tribe - Don’t try to shoe-horn yourself into a founder community that was designed for a 26 year old. (FWIW I was once a 25-year-old founder with a robust community). The advice that makes sense for a 25-year old entrepreneur doesn’t make sense for you. You should not work 90-hour weeks if you have kids and a spouse. You shouldn’t empty your 401k and your savings into your startup if you’re over 40. But, make sure you find a community which is some combination of group therapy, mentorship, and tactical advice. I built Punks & Pinstripes specifically for the Entrepreneur Exodus founders, and Entrepreneurs in corporate executive leadership. We’d love to hear from you if you’re one of us.
2. Fix What’s Broken - Someone who spends the first 18 years of their career trading derivatives at a broker dealer, or managing workflows for a large cap insurer will see billion-dollar inefficiencies that aren’t visible to anyone else. Equally, you’ll see cultural and political dysfunction in your legacy industry that makes people sacrifice essential progress for self promotion and self preservation. That is the unfair competitive advantage of the entrepreneur exodus. Capitalize on that unfair advantage. 
3. Be a Bada$$ - not an A$$hole - The entrepreneur exodus tends to come from industries like investment banking, construction, and insurance where the incumbents are over 100 years old. Many of these industries have never seen a new entrant. Your highest probability for success is selling a solution back to the industry you left that makes them more efficient. Leave gracefully, and with love. 

Bottom line: be more like Bobbie. 

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