Jan 31, 2023 · 1h 15m · founders-journal
Exclusive: Selling My Company & Making Life-Changing Money
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The Crazy Ones, co-host Jesse Pujji joins Alex Lieberman to break down the complete 13-year journey of building, scaling, and selling performance marketing agency Ampush to Tinuiti in a life-changing private equity exit.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Alex holds 19.3% of the talking time here. How this is scored →
Alex as informed peer 3.9 Guest teaching 4.2 Guest disagreement 0.4 Alex pushing back 1.4
speaking balance: gold is Alex, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:08:15 Rejecting the Entitlement / Hunger Premise
Jesse directly rejects Alex's question premise about instilling hunger through hardship, arguing instead for motivation driven by love and curiosity rather than fear.
Hardest push from Alex ▶ 48:30 Pressing on Why Jesse Didn't Contact the Buyer DirectlyAlex refuses to let Jesse gloss over his discomfort during negotiations and pointedly asks why Jesse didn't step around internal politics to directly call the buyer CEO.
Biggest teaching moment ▶ 6:23 Demystifying PE Multiple ArbitrageJesse clearly breaks down how private equity firms buy smaller earnings streams at low multiples and blend them into larger platforms trading at much higher multiples.
Alex holds their own ▶ 35:35 Alex Sharing His Banker Experience at Morning BrewAlex demonstrates his deep familiarity with M&A processes by explaining how boutique advisors who know the exact industry buyer universe create transaction leverage.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Alex as informed peer | Guest teaching | Guest disagreement | Alex pushing back | Why |
|---|---|---|---|---|---|---|
| Sale Announcement and Ampush Name Origins | 3 | 2 | 1 | 2 | Alex opens with playful banter about the acquisition announcement and immediately presses Jesse on the sale price. Jesse deflects gracefully, sharing the college origin story of Ampush's name. | |
| The Buyer Profile and Private Equity Multiples | 5 | 6 | 0 | 1 | Alex demonstrates an understanding of private equity roll-up strategies in middle markets. Jesse builds upon this by educating the audience and Alex on multiple arbitrage and equity roll-over mechanics. | |
| Early Bootstrapping, GLG Hacks, and Initial Hustles | 3 | 5 | 0 | 1 | Jesse shares the founding story, including how he leveraged Goldman Sachs's GLG subscription and created paid research decks. Alex acts primarily as an enthusiastic interviewer validating the bootstrapping hustle. | |
| Pivoting to Facebook Ads and Rapid Growth | 4 | 5 | 0 | 1 | Jesse details Ampush's transition into Facebook's self-serve advertising ecosystem and massive early scaling. Alex interjects with sharp founder insights on copying competitor funnels to bootstrap growth. | |
| Valuation Misalignment and the Red Ventures Deal | 4 | 4 | 1 | 2 | Jesse opens up about his 30-year-old ego chasing a nine-figure valuation and the structured option deal with Red Ventures. Alex probes whether Jesse regretted not taking a full buyout earlier. | |
| Stepping Down as CEO and COVID-19 Disruption | 4 | 4 | 0 | 1 | Jesse explains stepping down as CEO right before COVID-19 hit and moving into a chairman capacity. Alex contextualizes the massive operational challenge of managing a transition right before a global shutdown. | |
| Preparing Ampush for Sale and Hiring Bankers | 5 | 5 | 0 | 1 | Jesse walks through preparing the business for sale and engaging investment bankers. Alex compares notes with his own experience hiring a boutique media M&A banker during the Morning Brew exit. | |
| Selecting Tinuiti and Navigating the M&A Process | 5 | 5 | 1 | 2 | Alex asks about price anchoring and timeline expectations in M&A processes. Jesse firmly explains why they never gave pricing guidance and notes how quickly Tinuiti moved compared to standard deal cycles. | |
| Deal Economics and Non-CEO Negotiation Dynamics | 4 | 5 | 1 | 3 | Jesse discusses navigating deal terms as a non-CEO chairman without direct rapport with the buyer's executive team. Alex pushes Jesse to explain why he didn't assertively build that relationship earlier. | |
| The Emotional Spectrum of Closing a Company Sale | 4 | 5 | 0 | 1 | Jesse details the emotional rollercoaster, from date pushbacks causing intense fear to feeling sidelined as an owner rather than the operating CEO. Alex helps unpack the human psychology behind catastrophic thinking. | |
| Closing Day Reflections and Family Celebrations | 3 | 3 | 0 | 1 | Jesse describes the surreal experience of waiting for the wire transfer, celebrating with his co-founder Nick, and arriving home to his family. Alex listens and probes the emotional weight of finality. | |
| The Essential Role of Spousal Support in Startups | 4 | 3 | 0 | 1 | Alex highlights Jesse's public gratitude toward his spouse, prompting Jesse to reflect on the immense sacrifices required of an entrepreneur's partner during early venture building. | |
| Rapid Fire: Wealth, Success, and Parenting Values | 3 | 4 | 2 | 1 | In a rapid-fire sequence, Jesse rejects the premise that his children need hardship-driven motivation, explaining that he hopes to foster love- and curiosity-based drive instead. | |
| Future Ventures and the Value of Enduring Relationships | 3 | 3 | 0 | 1 | Jesse outlines his plans for Gateway X and Kahani while concluding that relationships with employees, clients, and partners are the only truly enduring legacy of building companies. |
Statements from this episode (27)
Pujji: The first rule of selling your company is losing control
“Lesson number one of selling your company. It ain't your company anymore.”
Pujji: Private equity roll-ups profit through valuation multiple arbitrage
“One thing that just happens in businesses as your business gets bigger, investors pay a higher multiple. It's more stable. It's demonstrated more sort of staying power. And so what a lot of these private equity firms do, and we were sort of a part of this arbi…”
Pujji: Ampush management and CEO rolled over significant equity in Tinuiti sale
“Especially our management team and our CEO got a lot of equity. We got a little bit which was by design, but so we're riding a little bit with them in terms of what's, what's going to happen.”
Pujji: Ampush co-founders seeded the business with $33,000 each
“The three of us each decided to put 33,000 dollars in, which we had made kind of working on our Wall Street jobs. We were 25, 26.”
Pujji: Co-founder contributed two-thirds of his Carlyle salary to fund Ampush
“Chris had a Commitment to Carlisle. He was a private equity and he had nine more months left on his contract and he didn't want to burn the bridge and leave early. But we all agreed that basically we would treat ourselves as one entity and he would give up two…”
Pujji: Ampush revenue jumped from $100k to $2M monthly within 14 months
“In June of 2010, the business did a hundred grand in gross revenue. By August of the following year of 20 11, it was doing two million a month in gross revenue.”
Pujji: Ampush spent $50M-$100M annually managing Uber driver acquisition
“And like, next thing you know, we scaled them to 600 cities globally. We were spending 50 to a hundred million dollars a year with them on driver acquisition, getting drivers to sign up to be on the platform.”
Pujji: 80% of tech unicorns were Ampush clients at some point
“We had a stat that eight out of 10 unicorns have been ambush clients at some point.”
Rocket Fuel and Marin Software valuations dropped 80-90% by 2015-2016
“There was like companies like rocket fuel and Marin software that were trading. We were billion dollar market caps in 20, 12 and 13 by 20, 15, 16, they had gone down 80, 90%.”
Ampush sold minority stake to Red Ventures with nine-figure buyout option
“We ended up selling a minority stake to this really cool company called red venture. Add punctuation. And we actually gave them an option to buy the rest of the business for, you guessed it, nine figures.”
Lieberman: Red Ventures is roughly valued at $12 billion
“Red Ventures is like the biggest company you've never heard of. I think last I saw, you know, rough valuation on the business is like twelve billion dollars. It's a massive company.”
Jesse Pujji: Founder readiness matters more than timing valuation when selling
“I think most founders undervalue how important it is that they, it's a personal, it's such a personal choice.
So in the case of John, I mean, John was like, Hey guys, you know, we're going to sell this business or I might, you know, I need to change the scene…”
Pujji: Ampush traded pricing for multi-year client deals before selling
“We spent a lot of time in the beginning of 22, as an example, getting all of our most important customers into really long-term agreements.
Right.
So I'm like, these are going to be ironclad multi-year agreements.
And we may even gave up on price and certai…”
Pujji: Skipping an investment banker for Red Ventures talks was a mistake
“When we ran the Red Ventures process, we didn't use a banker. And I actually think it was a mistake.”
Pujji took a 15% payout discount to let his CEO pick buyers
“I think I said, 15%. I'll accept a 15% discount on mine in exchange for you choosing the right partner for you.”
Pujji: Ampush never provided pricing guidance to prospective M&A buyers
“We never gave pricing guidance because why would you do it? I mean, you know, if someone comes in, like, why would you signal?”
Pujji: M&A leverage flips once you hold written offers from serious bidders
“Once you have a real written offer in your hand from a serious party or a few, right. Then you, the leverage flips very quickly. First you're like getting, get around to fall in love with me. Oh, a few people falling in love with me. Okay. Now I get to pick an…”
Pujji: Highest bidder on Ampush EDU divestiture retraded deal in 2013
“I made that mistake when we divested the EDU business. I took the highest bidder and they're, and I'll say it publicly, they were scumbags. They retraded the deal. They kept adding time to the deal. You know, they had, they knew they had leverage. I was buildi…”
Lieberman: Buyers and sellers rarely act in good faith during M&A
“Most people do not act in good faith when they're buying or selling companies.”
Pujji Prioritized Cash at Close Over Earn-Outs in Ampush Sale
“The number one thing for me was cash at close for me and my family. You know, I wasn't running the business anymore. I don't control a lot of what's going to happen if there's an earn out or anything else like that.”
Pujji: M&A Advisors Deferred Decisions to Owners Over Non-Owner CEO
“The lawyers and accountants kept coming to me and Nick for every decision. And actually they left it with one of their jokes and we were doing like superlatives at the end of the deal. And one of our jokes was John was the most left off person of emails. And i…”
Pujji: High-stakes negotiations should be reframed to increase trust, not erode it
“Typically when you go through like a salary negotiation with someone or a challenging situation, like Everyone basically prices in that you're going to hurt your trust with that person a little bit. I'm going to piss them off a little bit, but we'll get to a p…”
Former Ampush employees also received payouts after the company's acquisition
“Two days after the deal, we announced it to the employees and former employees. Cause they were all getting paid.”
Pujji: Spousal Support Is the Most Unseen Factor in Startup Success
“I think it's one of the most unseen roles in any kind of success like this and I'm, even now, we're still unpacking sort of, you know, my appreciation, gratitude, the things I didn't even know I was feeling or know that I needed, that I was getting from that”
Pujji: Completing a company exit fundamentally changes how the world treats you
“Getting it across the finish line matters to the world, like people, the way you're treated, the way kind of that, that success”
Pujji: Children will not receive unearned money or inheritances without work
“I'm not, there's not going to be a lot of free money given between me and them. And I don't just mean when they, you know, when I die, which is also probably not going to happen, but you know, like they'll, if they get allowances, they'll do chores for them. I…”