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My First MillionBREAKING: Shaan Sells the Milk Road - A Conversation With the Buyers
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Milk Road acquisition announcement and why the buyers matter
Shaan opens with the news that The Milk Road has been acquired and frames the episode as a conversation with the two buyers. He explains he still owns a minority stake and wants listeners to understand both the deal and who these new owners are.
- •Shaan shares that The Milk Road was acquired and he can finally discuss it publicly
- •He emphasizes the buyers as the main reason he wanted to do the deal
- •He previews the dynamic between the two buyers: one detail-obsessed workhorse and one “shortcut” problem-solver
- •He sets expectations that the conversation shifts from deal talk into story-driven lessons
Why the buyers stayed under the radar (and the ‘did you plan this?’ fan encounters)
Shaan asks why Michael and Kendall aren’t public or promotional despite their track records. They talk about shyness, not feeling the need to be visible, and react to a day where multiple fans recognized Shaan in public.
- •Kendall says it’s mostly shyness and not thinking public presence was necessary
- •They describe multiple consecutive fan interactions in San Francisco and Kendall jokes Shaan staged it
- •They tell the odd “came from the hospital looking for Shaan” encounter
- •Shaan contrasts his own public persona with their low-key approach
How the deal began: a growth outreach that turned into ‘we gotta buy this’
The buyers explain how they discovered Milk Road, admired its writing style, and initially saw it as a benchmark for content. A growth conversation with Ben turns into a serious acquisition intent almost immediately.
- •Kendall says their finance teammate shared Milk Road internally and they became subscribers
- •They admired the mix of humor and information density and connected it to their own content goals
- •Ben reached out with an ad/growth pitch, and the buyers took the meeting mainly to meet the team
- •Michael says within minutes they were messaging privately that they needed to buy Milk Road
Shaan’s impulse to sell, plus credibility checks and early deal turbulence
Shaan recounts how—on the same day as the first serious contact—he impulsively asked Ben what they’d sell for. He describes realizing the buyers were far from “a kid with a website,” and shares how the deal nearly fell apart multiple times.
- •Shaan tells the story of asking Ben, out of nowhere, what price he’d sell for—and deciding to test the market
- •Shaan realizes the buyers’ background includes large business outcomes and treats them as serious acquirers
- •They reference the “rule of five” idea that deals fall apart multiple times before closing
- •Shaan sets up a direct question about how well Milk Road negotiated
Deal negotiation grades: what went well and what surprised the buyers
Shaan asks for a blunt assessment of how Milk Road negotiated. Michael and Kendall give different grades and explain the moments that caused friction, including a diligence surprise around gambling-related revenue and how it intersected with a non-compete.
- •Michael gives an A-minus while Kendall says closer to a B and notes everyone had walk-away moments
- •They describe multiple points where one side thought the deal wouldn’t work
- •Michael says a diligence surprise was the amount of gambling sponsor revenue relative to their expectations
- •They agree that surfacing certain issues earlier could have reduced late-stage renegotiation stress
Why buy Milk Road: brand-powered SEO, content distribution, and bear-market resilience
The buyers explain the acquisition logic: the Milk Road brand strengthens their SEO strategy, and the newsletter complements their website ambitions. They also highlight that Milk Road grew through a crypto downturn and had diversified advertisers.
- •Michael describes their core strength as ranking high-intent search terms via SEO and content sites
- •He argues Google rewards brands people search for directly, and Milk Road already has that signal
- •Kendall says the newsletter and website channels complement each other for reaching different user behaviors
- •They point out Milk Road’s growth and profitability during the crypto winter and its diversified advertisers
Why Shaan sold: knowing his strengths—and betting on the buyers’ operating style
Shaan explains selling wasn’t about the business failing; it was about fit, energy, and long-term ownership. He contrasts his preference for starting things with the buyers’ willingness to grind, optimize, and execute over years—important because he kept equity.
- •Shaan says he’s strong at creating something from nothing but less energized by long optimization cycles
- •He describes Michael’s intense attention to detail and day-to-day operational consistency
- •Shaan frames Kendall as the complement: a clever shortcut-finder who solves puzzles differently
- •Shaan links the decision to his retained minority stake and desire to see the business’s potential fully realized
Kendall’s shortcut playbook: Uber/Lyft credits and the Tesla referral ‘Roadster’ hack
Kendall tells stories that show how he uses SEO and referral programs to create outsized outcomes. He explains building pages that ranked for referral searches and converting that traffic into credits and high-value rewards.
- •Kendall explains monetizing a Lyft-vs-Uber comparison site with referral links to earn credits for years
- •He describes ranking for “Tesla referral code” and sending large volumes of referrals
- •He explains the top prize mechanics and says he earned roughly 1.75 Roadsters’ worth of rewards
- •He shares distributing the strategy across family members’ codes to multiply potential outcomes
How they learned the SEO affiliate game: poker-era discovery and ‘misspelling’ arbitrage
Both Kendall and Michael explain how poker referral programs taught them affiliate economics. Kendall shares an early tactic: exploiting misspellings before Google autocorrect, while Michael describes learning from affiliate forums and selling his first site.
- •Kendall discovers poker sites pay for referred players and starts paying friends to deposit to capture spread
- •He says building websites became the path to scale from friends to strangers
- •Kendall’s breakout: ranking pages for misspellings of ‘Paradise Poker’ before autocorrect existed
- •Michael describes the poker affiliate community, starting a site with borrowed money, and selling an early site for $3,200
Kendall’s major gambling business: New Jersey focus, competitor partnership, and selling twice
Kendall explains a non-obvious pivot after online poker collapsed: focusing on New Jersey’s regulated market when others looked offshore. He details combining with a key competitor to dominate the market, gaining pricing power, and structuring a deal that led to a second payout as more states legalized.
- •Kendall describes choosing regulated New Jersey online casino/poker when regulators restricted promoting both regulated and offshore
- •He recounts partnering with a major competitor to effectively control the small market and improve leverage
- •He says affiliate payouts reached very high levels due to market power
- •He explains selling New Jersey first while retaining economics in future states, then renegotiating for a large second payout when expansion accelerated
Michael’s path to JM Bullion: failures, fraud shocks, and the ‘why would anyone buy from us?’ reset
Michael tells how he sold a gambling business young, struggled through failed experiments, and then found gold as a new arena. He shares early JM Bullion chaos—fraudulent orders and operational naivety—then explains the turning point: brutally comparing themselves to competitors and choosing a clear lever to win.
- •Michael says he sold a later gambling business for $565,000 at 19 due to uncertainty and dropped out of college
- •He shares a failed $25,000 purchase of a viral site that quickly received a cease-and-desist
- •He recounts early JM Bullion fraud that drove the business account negative and forced additional capital injection
- •He describes scoring competitors and concluding they were worse at everything, then deciding to undercut on price as the initial lever
Scaling pains and the first angel check: ‘affiliate speed’ trust and survival funding
As revenue grows, Michael explains the capital intensity of inventory and the difficulty of getting institutional money. Kendall describes investing quickly without heavy paperwork, and they reflect on how speed, trust, and leverage shaped that early deal-making style.
- •Michael explains why the business was capital-intensive: inventory needed to be on hand to ship quickly
- •He says outreach to many investors got no responses, forcing them to seek alternative funding
- •Kendall describes investing while staying non-operational, based on confidence in Michael’s ability to execute
- •They describe ‘affiliate speed’—fast handshake-style decisions and wiring money quickly
Hard-earned lessons: delivery disputes, domain squatting, and Kendall’s regulator scare
They swap memorable incidents that mix pain and learning. Michael tells a near-disastrous customer dispute that threatened trust and sales; he also shares domain typo plays around Facebook. Kendall recounts a regulator confrontation that caused intense stress and a health scare before resolving into a fact-finding meeting.
- •Michael describes a major delivery dispute that led to a damaging online complaint and a steep sales drop
- •He explains he nearly refunded $20K out of guilt before the customer’s story unraveled
- •Michael shares typo-domain strategies (Faceboom and facebookcom) and the legal limits of that approach
- •Kendall recounts being summoned by regulators, fearing arrest, and later learning it was largely informational once clarified
Lifestyle ‘hacks’: twin expert schedules, private chefs, and outsourcing for focus
Shaan asks about unusual lifestyle choices, and they answer with examples of paying for leverage at home. Kendall describes hiring a twin expert to impose a synchronized schedule, while Michael explains adopting a personal chef for healthier, decision-free eating and more focus on work.
- •Kendall describes hiring a twin expert for the first months to train parents and synchronize the twins’ routine
- •They emphasize the benefit of shared schedules (sleeping and eating in sync) to reduce chaos
- •Michael describes hiring a chef after hearing Kendall’s experience and realizing the efficiency gains
- •They discuss the mindset shift from ‘how do I fix this’ to ‘who can fix this for me’
Operating philosophy: bootstrapping vs VC, long-term conviction, and crypto’s case (and critiques)
They compare their self-funded style to Silicon Valley norms and discuss tradeoffs: control and speed vs potentially smaller ceiling. The conversation then shifts into crypto beliefs, including why they think digital money needs to improve, what they found shocking during industry blowups, and what the strongest criticisms are.
- •Michael says bootstrapping enables control, long-term thinking, and fast internal decisions without outside pressure
- •They acknowledge VC can enable larger outcomes but changes incentives and governance dynamics
- •They argue current money movement can be frustratingly slow or broken, using a wire-transfer story as an example
- •Michael steel-mans crypto criticism: scammers thrive due to fewer checks, even if the underlying tech isn’t the scam
Outlier outcomes and closing: doing the work, hiring, and where to find them
They reflect on learning from quiet industry “legends,” the value of thinking in 5–10 year increments, and Shaan’s framework for engineering outlier outcomes. They close with social handles, a light Twitter moment, and a note that Milk Road is hiring and seeking strong talent.
- •Michael explains a realization that top operators often don’t blog or seek attention—they focus on execution
- •He shares a mentor’s influence: zooming out to reduce emotional volatility and survive setbacks
- •Shaan frames the Milk Road sale as an ‘outlier’ move: finding the right buyers for a down market and long-term conviction
- •They share where to find them online, joke about first tweets, and announce Milk Road is hiring to scale quickly
Publisher timestamps
- 0:00Shaan's Intro
- 4:30Why Michael and Kendall are under the radarRead this chapter
- 13:30Stories of hacking SEO
- 16:00Why Shaan decided to sellRead this chapter from 16:01
- 43:00How Michael and Kendall got into the gold businessRead this chapter
- 56:30Why you should compare yourself to your competitors
- 1:01:30How Kendall's first business almost got him arrested
- 1:05:45Life hacks
- 1:12:30Business philosophies
- 1:30:00Creating outlier outcomes
