What Led You into Apparel with Mountain Khakis?

My guest today is Mac Lackey, an entrepreneur who has founded and sold six companies, each with 7-and 8-figure exits - including two back-to-back internet businesses during the dot-com boom.

In this episode, Mac breaks down the exact mindset and playbook that helped him turn businesses into life-changing exits. He shares the story of advising one company who was struggling to sell for $25 million… and guiding them to restructure and close for $42 million in cash just months later.

Sponsors:
This episode is sponsored by CapitalPad, the marketplace that connects acquisition entrepreneurs with investors who want exposure to small-business deals. Operators list live deals in one place; investors get standardized terms, governance, and distributions. If you are raising for a deal, or you want to back great operators, visit https://capitalpad.com/

Our sponsor Spacebar Studios builds and runs your newsletter end to end, so you stay top of mind with founders, brokers, LPs, talent and your customers without adding to your workload. Strategy, writing, design, sending, and list growth are handled. HoldCo Builders listeners also get a two-week free trial. Start with a free intro call at https://www.spacebarstudios.co/inquire

We discussed:
0:00 Who is Mac Lackey + Spanish football club owner
0:34 Early life: football-first, scholarship, brief pro career
1:28 First company
3:06 Early internet wave (1998 eight-figure exit in mid-20s)
5:24 Post-exit: acquirer IPOs (’99); starts a football media company
9:08 Building the largest non-televised football content shop:14-month sale (2000) during dot-com crash
12:20 The “strategic value vs financials” lesson and buyer’s lens
14:50 Sponsor: CapitalPad
20:14 Engineering a bidding war in London; fast LOI from competitors
27:53 Sponsor: Spacebar Studios
29:02 Third company: interim CEO, roll-ups, misaligned risk appetites and sells stake (which later becomes a nine-figure outcome)
33:23 Life design shift: optimizing for freedom of time after first child
48:08 Exit DNA: optionality, 10–100x ROI examples; common fixes (founder dependency, buyer math, estate/tax prep “two years + 1 day”)
1:02:52 Bet on people

Support our Sponsors:
CapitalPad: https://capitalpad.com/
SpaceBar Studios: https://www.spacebarstudios.co/inquire

Reach out to Mac: https://maclackey.com/mikk/

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This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions.