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My First MillionFrom Design Agency To $419 Million Holding Company In 8 Years
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WHAT IT’S REALLY ABOUT
Jeremy Giffon Shares Tiny's Acquisition Playbook, Negotiation Tactics, and Best and Worst Deals
- Tiny began when Metalab's free cash flow, in the low millions a year, was redeployed into buying businesses, starting with Dribbble, which Andrew, Chris and Jeremy knew as users and fans.
- Giffon argues that heavy financial modeling is mostly a comfort blanket and that the real edge comes from getting a no-brainer price and offering the seller trust, speed and certainty.
- He describes negotiation tactics learned from Chris: make a low offer then stay quiet, reframe the negotiation as both sides solving a shared problem, and ask what would need to be true for the deal to work.
- Giffon says cold emailing is a hugely asymmetric opportunity as long as you show up prepared and interesting.
- His deal stories include the Dribbble first deal, a worst deal where he ignored red flags about a dishonest seller, a 25X exit on Mealime, and a nearly free acquisition booked at a $36 cost basis.
IDEAS WORTH REMEMBERING
5 ideasStart with a concrete deal, not an abstract plan
Giffon says it is far better to begin with a specific target like Dribbble than to announce you're starting a fund or holding company in the abstract.
Detailed financial models are largely a comfort blanket
Giffon says he eventually made up the assumptions in Andrew's discounted cash flow spreadsheets, and cites the Barclays Facebook IPO report as an example of modeling that missed by an order of magnitude.
Win deals on more than price
Giffon says Tiny was rarely the highest bidder but often won because it offered honesty, speed and the ability to close, while higher offers often turned out not to be real.
After making an offer, stop talking
Chris taught Giffon that people start negotiating against themselves if you float an offer and stay silent, and Giffon says negotiation can come down to who tolerates discomfort longer.
Frame negotiation as both sides facing the problem together
Giffon prefers sitting on the same side of the table and treating the gap in price as the problem, which helps uncover what the seller actually cares about.
WORDS WORTH SAVING
5 quotesOne very cynical way of looking at negotiation is that it's just who can bear to be uncomfortable longer.
— Jeremy Giffon
In a traditional negotiation you're sitting across the table from one another, and the way that I really like to reframe it is you're both sitting on the same side, and what's on the other side of the table is the problem.
— Jeremy Giffon
My favorite question is what would need to be true? So it's like, okay, you wanna sell your business for $100 million. What would need to be true for me to pay $100 million for it?
— Jeremy Giffon
There's always a scarcity of talent. Like no matter who you are and how much money you're worth or whatever, there's a scarcity of really awesome people.
— Jeremy Giffon
It is funny how you just get the blinders on when something is so good, and I think we've all made that mistake.
— Jeremy Giffon
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SPEAKERS
Sam Parr
hostEntrepreneur and co-host of the My First Million podcast.
Jeremy Giffon
guestAcquisitions/operator executive associated with Tiny/MetaLab, discussing deal sourcing, evaluation, and negotiation.
Shaan Puri
hostEntrepreneur and co-host of the My First Million podcast.
High quality AI-generated summary created from speaker-labeled transcript.
