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My First MillionThis Entrepreneur Makes $100M+ With A Portfolio Of 10 Businesses
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Meet Michael Girdley and his 10-business holdco portfolio
Shaan and Sam introduce Michael Girdley and the wide-ranging set of businesses inside his holding company, from fireworks to software to coffee. They set the stage for a conversation about how a multi-business portfolio actually works in practice.
- •Shaan outlines several businesses in the portfolio, including Alamo Fireworks, Dura Software, a drive-through coffee chain, and the hiring service Near
- •Sam summarizes the portfolio scale as over $100M in revenue and 750+ employees
- •Michael confirms the broad portfolio structure and that Shaan has used Near to hire successfully
“How rich are you?”: Revenue vs ownership, cash flow vs compounding
The hosts push on what “$100M+ in revenue” really implies for personal wealth and liquidity. Michael explains that he owns varying percentages across holdings and intentionally balances long-term compounders with cash-flowing businesses.
- •Shaan challenges the common confusion between revenue, profit, and personal take-home money
- •Michael describes structuring the holdco for flexibility across different opportunity types
- •He explains that some holdings are designed to compound rather than pay out cash
- •Michael notes he often owns minority stakes (e.g., 30–60%) rather than 100% of operating companies
Portfolio math and reinvestment decisions (margins, debt, and where cash goes)
Sam and Michael get more concrete about typical profitability, margin expectations, and what happens to earnings across small-business holdings. Michael emphasizes reinvestment and acquisition-focused capital allocation when he doesn’t see better alternatives.
- •Sam asks how much profit the portfolio generates and how distributions work with partial ownership
- •Michael cites typical small-business EBITDA margins in the 15–20% range
- •He describes evaluating free cash flow after items like debt service
- •Michael says most businesses reinvest earnings into assets and new acquisitions rather than paying out
The fireworks business reality check: high stress, seasonal cash flow, and operational complexity
The conversation turns to Alamo Fireworks, which Sam and Shaan initially assume might be a simple cash cow. Michael explains why fireworks is difficult: long lead times, upfront cash needs, and profits concentrated into a tiny window.
- •Michael calls fireworks one of the hardest businesses to run and describes heavy upfront preparation
- •He explains the need to forecast demand 6–12 months ahead and fund inventory and operations early
- •The company runs about 200 locations across Texas and sells mainly around July 4th and New Year’s
- •Michael says they don’t break even until late on July 4th and customers buy at the last minute
How the fireworks business got better: systems, people, and Michael stepping back
Shaan asks about “operating hacks” to make the fireworks business less painful. Michael explains that the biggest improvement came from realizing he wasn’t the right operator and putting the right people and basic systems in place.
- •Michael says he’s not an optimization-focused operator and finds that work boring
- •He credits growth in recent years to getting the right people running the business
- •He mentions upgrading to digital point-of-sale from handwritten systems
- •Michael frames improvements as a team effort rather than personal operational genius
Best cash cow: the coding bootcamp (low capex services + meaningful impact)
After fireworks, Shaan asks which holding is the most attractive from a cash-flow standpoint. Michael names the coding bootcamp, emphasizing low capital expenditure, service economics, and the personal satisfaction of helping people change careers.
- •Michael identifies the coding bootcamp as the best cash-flowing business in the portfolio
- •He highlights services economics and low capex as key advantages
- •Michael says the business is meaningful because it helps people transform their lives
- •He describes it as low eight figures with margins consistent with the 15–20% range discussed earlier
Off-the-beaten-path curiosity: China factory trips, boxes, and “stumbling” into opportunities
Shaan digs into Michael’s habit of exploring non-obvious parts of industries and places to learn how things work. Michael tells stories from China and elsewhere that show how curiosity feeds deal flow and new business ideas.
- •Michael describes traveling to China to train teams to buy fireworks in a regional manufacturing hub
- •He explains how repetitive factory visits led him to detour into a box factory to learn more
- •Michael shares observations about production constraints (like wastewater rules affecting operations)
- •He tells a story about watching drive-through coffee demand near Walmart HQ and deciding to start a coffee business
Berkshire Hathaway meeting: pilgrimage, people-watching, and “anti-advice” lifestyles
Michael reacts to Shaan’s question about whether the Berkshire Hathaway annual meeting is worth attending. He describes it as a must-do experience for capitalists and the hosts riff on how Buffett and Munger’s habits contrast with modern hustle culture.
- •Michael says the Berkshire meeting is worth attending at least once and praises the people-watching
- •He describes the atmosphere as a mix of investing devotion and spectacle
- •Michael notes the age and on-stage presence of Warren and Charlie during the event
- •Shaan contrasts their lifestyle with common social-media “success” routines and information overload
Near and the “apex of automation”: building companies through associates and partnerships
Sam asks which other portfolio company feels like “easy mode,” and Michael points to Near (hirewithnear.com). Michael explains how it fits his ideal: delegated execution, strong market pull for overseas hiring, and an “entrepreneur-in-training” pipeline for founders.
- •Michael describes Near as requiring little day-to-day work from him while keeping a substantial stake
- •He explains the demand driver: executives struggling to hire and turning to overseas talent
- •Michael shares that he personally employs overseas team members he’s never met in person
- •He explains his associates program: salaried mentoring leading to starting companies together
Hiring great CEOs and why holdcos are harder than they look
The conversation shifts to how Michael incentivizes leaders and why operators choose to partner with him. He also explains common misconceptions about holding companies and why the holdco role requires resisting the operator impulse to jump in and fix everything.
- •Michael says CEO/leader comp varies widely by seniority and business stage, from salary-only roles to highly paid executives
- •He says equity grants can range broadly depending on the situation and commitment
- •Michael explains why partners give him equity: early idea work, significant capital, guarantees, and strategic/connection value
- •He argues many people underestimate holdco difficulty and that the job is the opposite of operating a single company
Unpopular opinions and “dope” business philosophy: brands, fun budgets, and mental real estate
The hosts riff on building businesses (and personal brands) that prioritize “dope” outcomes, not just monetization. They share examples of intentionally doing funny or creative things, then land on how recurring “signature” preferences (like Chili’s) can create memorable identity.
- •Shaan and Sam discuss doing things because they’re fun and distinctive, even without direct short-term payoff
- •Shaan describes setting aside a “do cool shit” budget and why it keeps teams engaged and signals confidence
- •Sam shares examples from The Hustle of sending unconventional emails for humor and brand energy
- •Michael shares the PopSockets growth story and Shaan explains the value of owning a quirky “signature” like Chili’s that people associate with you
