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Episode 4 · 2026-06-28

The $3 Trillion Opportunity Most People Are Ignoring

with Leon Leibovich

Leon went from arriving in America with $200 and no English to building 15 businesses and advising owners on how to sell companies worth millions. He breaks down the $10 trillion wealth transfer happening over the next decade and why buying a business might beat starting one for people just getting

business acquisitionentrepreneurship through acquisitionsuccession & exit planning

show notes

  • came to US at 26 from former Soviet Union. $200 in pocket, daughter in his arms, didn't speak english
  • master's in applied math (St Petersburg) + second master's from Northwestern
  • never worked in math. says business is just optimization, stats, probability. applied the brain to deals instead
  • ran ~15 businesses of his own. started in insurance/financial services
  • 6 yrs running insurance agency then started a PRO SOCCER CLUB?? played pro himself. turned the club into a league bc no money in it
  • distribution business next, traded w eastern europe when it opened late 80s/early 90s. blew up. sold to his partner
  • soccer transfer agency. US company operating in europe. moved 24 players into premier league, bundesliga etc. made real money
  • joined a firm w 120 partners, mostly ex fortune 500 CFOs/CEOs. called himself the "black sheep." learned the M&A game there
  • what he does now: ownership transition advisory. helps owners sell / plan succession / exit
  • NOT advisory for PE. they ORIGINATE businesses for PE. structure deals for the seller's benefit
  • deals he does: $3-5M to $50M+ revenue. only profitable businesses. no startups, no VC

big idea:

  • next 10 yrs ~$10 TRILLION in private businesses change hands. baby boomers aging out, have to sell
  • most owners don't even know their business is sellable. don't know WHEN to sell (not at the bottom, sell when it's up) or HOW
  • structure is everything when selling: proper value + tax advantage + keep employees + protect the legacy/culture
  • can sell to: individual / financial buyer / strategic buyer / institutional (PE). that's why you need an advisor

on young people:

  • thinks buying a business is one of the best paths. esp trades. plumber/electrician can work for a company then BUY it. don't need a degree for that
  • low on money? get a partner, family help, or SBA loan. ways to acquire
  • BUT $10-30M businesses not realistic for someone my age early on. later, sure
  • contradiction to push on: said skip-college-and-buy could work, then said college IS necessary in his opinion. didn't fully reconcile it
  • his actual line: get some experience first, then look for something for yourself

quotes/moments:

  • "it was like an ocean for me. didn't know where to go what to do"
  • went WITH the flow, not against the system. took opportunities as they came
  • loyal family man, 8 grandkids, brings it up unprompted
  • whole vibe = no safety net, had to do something, so he did

follow ups i didn't ask:

  • pin him on college contradiction
  • HOW do you actually find a business to buy at 17-20
  • what's a realistic first deal size for someone broke