Dec 17, 2022 · 1h 40m · my-first-million
BREAKING: Shaan Sells the Milk Road - A Conversation With the Buyers
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Shaan Puri announces the acquisition of his crypto newsletter, The Milk Road, sitting down with buyers Mike Wittmeyer and Kendall Saville to unpack the mechanics of the deal and explore their bootstrapped journeys from early SEO affiliate pioneers to nine-figure e-commerce and media exits.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. The hosts hold 42.4% of the talking time here. How this is scored →
The hosts as informed peer 5.1 Guest teaching 4.2 Guest disagreement 1.0 The hosts pushing back 1.9
speaking balance: gold is the hosts, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 11:58 Grading the negotiation and flagging undisclosed gambling revenue
Mike Wittmeyer directly challenges the smoothness of the deal by bringing up undisclosed gambling sponsor revenues that almost broke the acquisition during diligence.
Hardest push from the hosts ▶ 10:55 Putting the buyers on the spot regarding negotiation leverageShaan refuses to let the buyers off easy, explicitly demanding an honest grade on how well the Milk Road team negotiated the sale.
Biggest teaching moment ▶ 39:00 Kendall explaining New Jersey regulated affiliate market powerKendall educates Shaan on how cornering a single newly regulated market gave them pricing leverage of $1,000 per lead, resulting in a $50M dual buyout.
The host holds their own ▶ 1:30:20 Shaan breaking down the outlier strategy for selling companies during bear marketsShaan demonstrates deep expertise in M&A psychology, articulating why conventional advice fails when engineering outlier deals during a market downturn.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | The hosts as informed peer | Guest teaching | Guest disagreement | The hosts pushing back | Why |
|---|---|---|---|---|---|---|
| Welcome, Staying Low Key, and Fan Encounters in SF | 4 | 1 | 1 | 2 | Shaan sets up the episode with an intro framing and asks Kendall and Mike why they keep a low profile despite their wealth. The guests are relaxed, humorous, and completely collaborative. | |
| How the Acquisition Deal Came Together | 6 | 2 | 1 | 2 | Shaan and the guests recount how the acquisition began from an ad deal outreach and turned into a buyout. Shaan demonstrates domain knowledge of business exits and M&A psychology. | |
| Grading the Negotiation Process and Hidden Hurdles | 5 | 5 | 2 | 3 | Shaan puts the buyers on the spot asking for a letter grade on his deal negotiation. Mike and Kendall point out diligence oversights regarding gambling sponsor revenue that almost derailed the deal. | |
| Founder Personalities and Mike's Uphill Skiing Mentality | 6 | 3 | 1 | 2 | Shaan articulates his self-awareness as a starter rather than an optimizer, contrasting himself with Mike's relentless grind mentality. The exchange is deeply mutually respectful and insightful. | |
| Kendall's Hacks: Tesla Roadsters and Rideshare Credits | 4 | 6 | 1 | 2 | Kendall walks Shaan through his inventive SEO hack that ranked for Tesla referral codes to earn free Roadsters and lifetime rideshare credits. Shaan mostly listens and reacts with amusement. | |
| SEO Origins and Misspelling Paradise Poker | 5 | 6 | 1 | 2 | Kendall details his early affiliate days exploiting Google's lack of autocorrect by deliberately misspelling Paradise Poker. Shaan connects the tactic to current trends like the Kia rebrand search confusion. | |
| Mike's Poker Affiliates and the $3,200 First Sale | 4 | 4 | 1 | 2 | Mike explains his initial poker affiliate website sale for $3,200 as a teenager and his brief stint with physical odd jobs. Shaan prompts him to share early entrepreneurial milestones. | |
| Kendall's Early Retirement Party at Lazy Bear | 4 | 3 | 1 | 2 | Kendall shares the story of throwing an early retirement party at Lazy Bear at age 33 following his first major sale. The group engages in lighthearted banter about keeping wealth under wraps. | |
| Pivoting to Regulated New Jersey Gaming to Build Catena Media Asset | 6 | 6 | 1 | 2 | Kendall breaks down the pivot to regulated New Jersey online gaming affiliate marketing, partnering with a competitor to form a monopoly, and selling to Catena Media for $50M. Shaan adds commentary on affiliate pricing power. | |
| Mike's Hard Reset: Dropping Out and the BrosIcingBros Blunder | 4 | 5 | 1 | 2 | Mike recounts dropping out of college, buying BrosIcingBros.com for $25K, and immediately getting hit with a cease-and-desist from Smirnoff. Shaan jokes about viral college marketing tactics. | |
| Pivoting to Physical E-Commerce: Founding JM Bullion | 6 | 7 | 1 | 2 | Mike describes the origins of JM Bullion from an initial affiliate shutoff to building a physical precious metals ecommerce giant and bringing Kendall on as the first angel investor. Shaan praises Mike's brutal self-assessment framework. | |
| Sponsor Message: HubSpot CRM | 2 | 1 | 0 | 0 | Short sponsor integration featuring HubSpot CRM and transition banter. Low dynamics and scripted host/voiceover elements. | |
| Kendall's Faceboom Domain Squatting Play | 4 | 6 | 1 | 2 | Kendall shares wild domain squatting stories including Faceboom.com and a terrifying encounter with New Jersey gaming regulators that triggered physical eye spasms. Shaan listens and reacts to the absurdity. | |
| Lifestyle Hacks: Twin Trainers, Private Chefs, and Delegation | 5 | 4 | 1 | 2 | Kendall and Mike discuss hiring specialized twin sleep trainers and private chefs for maximum cognitive efficiency. Shaan shares his own identical perspective on prioritizing personal health delegation. | |
| Bootstrapping vs. The Silicon Valley Venture Capital Model | 6 | 5 | 1 | 2 | The conversation contrasts bootstrapping cash-flowing affiliate businesses with the Silicon Valley venture capital path. Shaan and Mike evaluate the trade-offs of autonomy versus shooting for $10B outcomes. | |
| High Conviction Bets: Buying Bitcoin in 2013 | 7 | 5 | 1 | 2 | Kendall explains his 2013 Bitcoin thesis inspired by his father's domain name foresight. Shaan shares his personal anecdote about bubble psychology when his aunt mentioned Ethereum at a wedding. | |
| The Crypto Thesis, Market Crashes, and Downside Protection | 7 | 5 | 1 | 2 | Shaan and the guests discuss the macro thesis for cryptocurrency, bank friction with traditional wires, and separating underlying blockchain technology from bad actors and fraudsters in the space. | |
| Learning Twitter and Prioritizing Real Work Over Hype | 6 | 3 | 1 | 2 | Shaan teases Mike for posting his very first tweet on the day of the acquisition announcement, discussing the contrast between public hype building and Heads-down operational execution. | |
| Mentorship, 10-Year Horizons, and Outlier Deals | 7 | 6 | 1 | 2 | Mike shares the philosophy learned from an early mentor on viewing business in 5-to-10-year horizons. Shaan expounds on why outlier outcomes require acting counter to conventional market wisdom during downturns. | |
| Wrap-Up, Twitter Handles, and Hiring for The Milk Road | 6 | 2 | 1 | 1 | Shaan summarizes why he chose Mike and Kendall as buyers over higher bidders due to their track record and shared upside. Kendall puts out a hiring call for Milk Road talent. | |
| The EO Fitness Bet and the Ski Mountain Wipeout | 4 | 3 | 1 | 2 | Mike recounts his intense EO body fat challenge and closes with a hilarious story of attempting to backcountry split-board straight up a steep ski mountain in sub-zero wind. The show wraps on high energy. |
Statements from this episode (25)
Puri Predicts His Retained Milk Road Equity Will Surge In Value
“And they're people that I thought if I give them, you know, this company and I own, I still own a minority stake in it, that minority stake in five years is going to be worth a lot because I believe in these guys and what they've done.”
Wittmeyer And Saville Acquired Shaan Puri's Milk Road Newsletter
“We got together because you guys just bought my company. You bought the milk road.”
Puri: Buyers Previously Generated Multi-Hundred Million Dollar Exits
“So you guys, you'd built that. That was a Couple hundred million dollar company. And then you had done the same thing in the sports betting side. Same thing, like roughly a hundred million dollars worth of exits.”
Puri: Successful Acquisitions Typically Fall Apart Five Times Before Closing
“Somebody said this the other day, they go, the rule of, they call it the rule of five. They go, in any deal, it's going to fall apart five times. If it's going to get, if it's going to get done, it's going to fall apart five times.”
Wittmeyer: Bitfo would have walked away if final Milk Road offer failed
“At the end, like when we made that final, you know, the last little chunk, we were, that was it for us. We had said, we're walking if this doesn't work.”
Milk Road Deal Briefly Stalled Over Unexpected Gambling Sponsor Revenue
“One of the times it fell apart was we got into the diligence after we'd already agreed on a number and there was a little more gambling, gambling sponsor revenue there than we thought.”
Puri: The Milk Road Grew and Was Profitable During Crypto Winter
“Our business was still growing and generating revenue and profit during the crypto winter”
Saville Earned Unlimited Uber And Lyft Rides By Exploiting Referral SEO
“So basically on that site, the way I monetize it was here's my referral code when you sign up for one or the other and literally had unlimited Uber and Lyft for years. Literal years.”
Saville Earned 1.75 Free Tesla Roadsters Through SEO Referral Arbitrage
“So I earned like 1.75. I had sent more referrals, but I think Tesla was like, all right, you know, we're going to give you 1.75.”
Saville Paid for Senior College Year via Misspelled Poker Domain SEO
“Literally my last year of college, it was like paid for. I was basically like parents, like I've got this, you know, I've got room board, you know, the education because I'm making Free money basically online.”
Saville's New Jersey Online Casino Affiliates Earned $1,000 Per Referred Player
“We Were able to get a thousand dollars per player that we sent through New Jersey online casinos.”
Saville Netted Roughly $50 Million From Catena Media Affiliate Buyout
“And so, you know, it was part stock and part cash. So in total is around fifty million.”
Wittmeyer Sold His Online Poker Affiliate Business For $565,000 At Nineteen
“I sold, I was further into it. I sold for 565,000 and I was, I think, 19 then.”
Wittmeyer: Paid $25,000 to acquire unmonetized viral site brosicingbros.com
“Ended up working on a deal to buy it, and I gave him 25,000 dollars for it. There was no monetization at all.”
Wittmeyer: JM Bullion Benefited From Confusion With Johnson Matthey
“We knew so little about this space when we started that we named it JM Bullion using our initials and We had no idea that, like, one of the largest refiners of gold and silver in the world is Johnson Matthey, and so we actually got a big boost early on because…”
Saville Netted $23 Million From His Early JM Bullion Angel Investment
“You got like twenty three million.”
Wittmeyer: Early Ripoff Report review cut JM Bullion sales by roughly 30%
“There's a site called ripoffreport.com, where anyone can go on there and file, like, hey, this company or person screwed me, and he did that, and we were so early that, like, there were no jamboy in reviews anywhere, so when people searched that, that was the …”
Puri Prioritizes Paying For A Private Chef Over Hiring Extra Employees
“Any money I could spend on a car, a nice, nice whatever I would way rather do this. I would rather have one less employee at work and do more myself than like sacrifice on this.”
Wittmeyer: Bootstrapping Makes Massive Multi-Billion-Dollar Outcomes Much Harder to Achieve
“I think one thing you probably lose though, is it's, in my opinion, it's harder to have like the really big outcome. If like the things we're doing or historically have done, it's hard to, It'd be like a ten billion dollar company from that stuff. And I think …”
Saville Invested Hundreds Of Thousands In Bitcoin At $80 In 2013
“I probably put a couple 100,000 dollars in at that point.
But I was like, you know, I'll just wait it out.
At that point, I think it was around 80 to 90 dollars per Bitcoin.”
Wittmeyer: I Have Capital Trapped on Genesis
“We have, I have money on Genesis that I don't know what's going to happen to it, but that one was pretty stunning too.”
Wittmeyer: Milk Road Hits Record Subscriber Growth During Market Crash
“What's been interesting for the milk road and our businesses, you know, this has actually been for growth, a good thing, right? We cover the news and there's certainly been a lot of news. So we're seeing, you know, record subs coming in that the reader scores …”
Wittmeyer: Mentor invested $1M in JM Bullion despite losing processor
“To his credit, he put a million into JM shortly after Kendall did his first angel investment. Like a week before it was going to close. We had done all the documents. It was ready to go. Our credit card processor throws us out. And that was like half of our re…”