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My First MillionBREAKING: Shaan Sells the Milk Road - A Conversation With the Buyers
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WHAT IT’S REALLY ABOUT
Milk Road sold: buyers explain SEO playbook, deal, and philosophy
- Shaan announced The Milk Road’s acquisition and explained he sold despite strong growth because he’s better at starting businesses than optimizing them for years, while keeping a minority stake to retain upside.
- Kendall and Michael explained they pursued the deal after reading the newsletter and believing Milk Road’s brand strength and audience search demand would improve their SEO-based strategy and broaden distribution.
- The negotiation process nearly fell apart multiple times; the buyers said a major late-stage issue was realizing more gambling sponsor revenue existed than expected given one buyer’s gambling non-compete.
- Both buyers traced their business origins to poker-era affiliate marketing and SEO tactics, sharing stories of ranking for misspellings, capturing referral-program arbitrage (Uber/Lyft/Tesla), and learning through early failures.
- They contrasted their self-funded, control-oriented approach with VC-style scaling, arguing it enables fast decisions and long-term thinking but may limit the probability of the very largest outcomes.
IDEAS WORTH REMEMBERING
5 ideasShaan sold largely because the buyers fit his strengths-and-weaknesses and he still keeps upside.
Shaan said The Milk Road was growing quickly and profitable, but he’s more energized by starting something than by years of incremental optimization; he also wanted to stay involved via a minority stake while handing day-to-day compounding to operators he believes will grow it.
The buyers saw The Milk Road as a brand-and-distribution accelerant for their SEO-driven strategy.
Michael said their thesis was that having a real brand people search for (like Milk Road) helps Google reward the site, and Kendall added the newsletter and website together create multiple distribution channels; they also liked that the business was growing and profitable during a crypto downturn with diversified advertisers.
Deal friction came from late-arriving diligence issues, especially around gambling-related revenue.
Michael rated the seller-side negotiation highly overall, but said one breakdown came when they discovered more gambling sponsor revenue than expected because he has a gambling non-compete; he suggested surfacing that earlier would have enabled better planning and fewer surprises in diligence.
Their early edge came from exploiting distribution quirks: search intent + low competition + referral economics.
Kendall described learning affiliate marketing via poker sign-up incentives and then building sites to attract strangers, including ranking for misspellings before Google autocorrect; he also described hacking referral programs (Uber/Lyft and Tesla) by ranking pages for “referral code” searches and capturing large volumes of signups.
Their story includes big swings, big mistakes, and learning operational reality the hard way.
Michael described repeated early failures, including buying a viral “icing” site for $25k and receiving a cease-and-desist the next day, and later getting hit by large-scale fraud/chargebacks in the early days of JM Bullion; he framed these as painful but formative operational lessons.
WORDS WORTH SAVING
5 quotesI’m good at starting things. I’m good at finding the, the, the something from nothing. But taking the something and just fine-tuning it day after day, making it better, which is where most of the value is created in business, is, uh, not something that I just get super excited about.
— Shaan Puri
I feel like you’re gonna be right a couple times in your life. And if you think you’re gonna be right, swing big.
— Shaan Puri
I can’t work for someone else. Like, this is just not me. Uh, you know, I wanna work for myself, I wanna set my own hours, and I wanna make a lot of money.
— Michael Wittmeyer
I just took a really honest look in the mirror, and I said, "There’s no reason anyone would ever buy from us."
— Michael Wittmeyer
We need to get some help. Like, we need experts.
— Kendall Saville
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SPEAKERS
Shaan Puri
hostCo-host of My First Million and entrepreneur who sold The Milk Road newsletter.
Kendall Saville
guestEntrepreneur and one of the buyers of The Milk Road, focused on growth/distribution and deal rationale.
Michael Wittmeyer
guestOperator/SEO-focused entrepreneur (with background including building JM Bullion) and one of the buyers of The Milk Road.
High quality AI-generated summary created from speaker-labeled transcript.
