Gaming the System: An M&A Banker's Playbook for Engineering the Perfect Exit | Mike Bank

September 2, 2025

23mile

What does it really takes to build a business that’s ready to be acquired ?

Mike Bank’s career has been a masterclass in understanding and "gaming" the systems of finance and startups. He began by hustling his way into a role at Citibank he was admittedly underqualified for, a story that sets the stage for a journey defined by strategic thinking and a refusal to follow a conventional path. After four years in M&A, he famously quit with the answer, "I have no idea," plunging into the world of startups as both an investor and a founder.

This episode is a candid, unfiltered look at the realities of the venture world from someone who has sat on every side of the table. Mike shares the hard lessons from his two venture-backed startups: Pocket Social, which fell victim to the "Series A crunch" after VCs who had been his friends stopped returning his calls ; and Soho Labs, a co-working space that went head-to-head with the behemoth WeWork.

Drawing from his deep experience as an M&A banker and his current role leading small-cap acquisitions, Mike provides a clear playbook for founders on how to engineer a successful exit. He debunks common myths, explaining why you shouldn't be distracted by the exit early on and why a competitive market can be your biggest asset. He also shares the powerful mission behind his social enterprise, Underdog X, which helps non-traditional founders build sustainable businesses, often without venture capital.

This is an essential listen for any founder who wants to understand the unwritten rules of startups, venture capital, and what it really takes to build a business that’s ready to be acquired..

Agenda:

  • Gaming the System: An Unconventional Career Path

    • How he "gamed the system" to land an M&A role at Citibank despite being technically ineligible and underqualified.

    • His core philosophy of understanding the "game" being played—whether in job applications or startups—and optimizing to win.

    • Why he quit his lucrative banking career after just four years with the epic response, "I have no idea," driven by a desire for the freedom and impact of entrepreneurship.

  • An Insider's View on Venture Capital

    • The harsh reality of fundraising: his experience with Pocket Social and the "Series A crunch" that led to the company shutting down.

    • The painful lesson that VCs who are your friends when you have money will often ghost you when you need to raise a follow-on round.

    • His belief that true VC is for deep, innovative R&D (like "a rocket ship to Mars"), not just for market grabs and bribing customers with referral codes.

    • The story of his investors refusing to take their remaining capital back, which led to the pivot into his second startup, Soho Labs.

  • The M&A Playbook: How to Get Acquired

    • The most important rule for an exit: don't get distracted by it early on. Focus on building something people want first.

    • How to "hack the system" for an optimal exit: create a competitive process where multiple entities want your asset enough to outbid each other.

    • His take on the "companies are bought, not sold" adage, and why he's bearish on M&A as the primary outcome for most venture-backed startups.

    • A real-world story of a friend who successfully engineered a bidding war by playing two reliant corporate customers against each other17.

  • The Underdog's Champion: A New Model for Founders

    • The mission behind his social enterprise, Underdog X, which removes barriers to entry for non-traditional founders.

    • His "show up, do the work" model that replaces traditional screening with a chance for anyone to prove their grit.

    • Why he believes building a profitable, sustainable £50 million company can be a better personal financial outcome for a founder than a VC-backed unicorn.


      Memorable Quotes

    • On his career strategy: "What I have built my career around doing, which is gaming the system... if you understand the game that's being played, you can optimize to win that game."

    • On the reality of VC relationships: "If you've got money, everyone wants to be your friend. And as soon as you don't have money and you're asking, it's awful."

    • On what his acquisition targets need to prove: "Show me what you've done. Don't tell me what is possible in the future. That's the risk that I'm taking on.

    • On exit strategy: "Don't get distracted by the exit. I think the exit is a function of you doing everything else right.

    • On supporting founders: "Giving people a hand up, not giving them a handout... teaching people how to fish, not giving them fish.”

      Links & Resources Mentioned

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