Jeremy Giffon

Become an audience co-founder: build the business, give the creator equity

Jeremy Giffon's second-favorite opportunity: find a creator with a trusted audience, build or buy the perfect product for them, run it as CEO, and split equity. Audiences are still wildly underpriced relative to ad reads.

“And so I think there's a big opportunity to basically build a business around someone with an audience and come to them and say, look, like I will be the CEO of this thing. I think like, you know, um, this is the perfect product for you guys to like really organically use and like and talk about for a long time and I will run it and, you know, we'll split the equity or something like that. You know, Joe Rogan did this with Onnit and sold that company for a lot of money.”

Steal thisPick a creator you love, design the one product their audience would organically use, and pitch yourself as the operating CEO in exchange for split equity.

Most of a YC batch could find a podcaster and give them 30% as audience co-founder

Giffon argues the audience co-founder model is so underpriced that most YC founders could pair with a podcaster, hand them ~30% equity, and build a product the creator sells organically.

“but I think most people in a YC batch could find a podcaster and just say, okay, you're going to be the audience co-founder for this thing and we're going to give you 30% or something and we're going to work with you and it's going to be a product that you can sell very organically.”

A Wirecutter for 'won't kill you' products

Giffon wants a Wirecutter-style review business that vets every household item (clothing, bedding, cleaning products, food) for toxins and harmful chemicals. The problem runs the entire gamut of the home, and he says he'd use it every day.

“I would love to have a Wirecutter kind of thing, which is a great business for just like, this is the version of this thing that is not gonna kill you.”

Steal thisBuild a health-based Wirecutter that ranks the non-toxic version of every product in the house and monetize like the original.

Cheap but mission-critical: the golden criteria for compliance software

Giffon's favorite category is regulatory-compliance software (KYC, AML, banking rules, tenant vetting). The ideal target is relatively cheap but mission-critical, never gets ripped out, and is AI-resilient because the downside (fines, prison) is too high to trust to automation.

“And it's, you know, it hits that golden criteria, which is it's relatively cheap, but mission critical. That's like a really great one. And there's a bunch of these, there's all these, you know, for buying a house for, for vetting tenants, for KYC and AML.”

Steal thisHunt for software that's cheap relative to its budget but mission-critical, so it's sticky and never gets cut.

Front-run new regulation to be the only software provider for years

Giffon's tip for founders: watch what laws are about to pass or just passed, then be the first compliance provider for that rule. In niche areas you can be the only option for a couple of years, a huge head start.

“The other big opportunity for someone who's wanting to start a business is like you can front run these things, right? You can see what's going to pass, you can see what's just passed, and you can be the first provider for that and have a huge leg up, especially if it's a fairly niche thing. But you could very well be the only option for a couple of years, which is a huge advantage, right?”

Steal thisMonitor pending legislation and ship the compliance tool the day a niche rule passes to own the category before anyone else shows up.

The Boy vs the Guy: apprentice to a powerful principal for 2-3 years

Giffon's 'boy/guy' archetype: instead of joining a company for generic experience, become the protege or chief of staff to a billionaire principal who backs you and opens doors. Works best with a ~20-year age gap. Examples: Altman to Paul Graham, Blake Masters to Thiel.

“I generally think like if you want to start a company, you should just start a company. Don't go like work somewhere to get experience or whatever.. But I think this might be the sole exception, which it can really open doors of either investment or vouching or connections or whatever.”

Steal thisIf you're young and ambitious, spend 2-3 years as the apprentice to one powerful operator who will vouch for you, then launch.

A holdco is half portfolio, half giant operating company

Giffon warns investory founders that a holding company isn't just holdings: the other half is a large operating business (Tiny runs 1,200+ employees across its portfolio). Great investing skill is often the opposite of running a 1,200-person company.

“The other is that I think when the more investory type start them, they really don't appreciate a holding company is part of it is your holdings. The other half is a company. Like you just run a big operating business. You know, Tiny has, I can't remember, it's like north of 1,200 employees across the portfolio. Like that's a big business that you're running.”

Don't buy the Ohio plumbing company, start it

Giffon mocks the Harvard-Goldman-HBS resume that ends in buying an Ohio plumbing business. He argues a brilliant young person who simply moved to Ohio at 18 and started a plumbing company would dominate the state's incumbents.

“But I always think like, imagine if you had, you know, you're this brilliant young person. If you had just moved to Ohio when you were 18 and started a plumbing company, you'd probably control all the plumbing in the state. You know what I mean? Like you just wipe the floor with them. And it's always weird that people want to go through all these loops.”

Pre-fall vs post-fall: has life truly humbled this person?

Giffon's pseudo-biblical 'fall' model: a moment that truly brings you to your knees (death, bankruptcy, health scare) permanently changes you. Post-fall people are unshakeable; partnering with someone successful but pre-fall is a liability because their eventual blowup can be spectacular.

“after someone's post-fall, you can just kind of see it in their eyes that they've been through worse. And so they're not going to— it's just not going to shake them that much versus somebody who's pre-fall. And by the way, you can become very successful, you can be late in life, but nothing bad has ever really happened to you. And I view that as kind of a liability in some sense of if you're going to partner or work with them”

Special situations: buy great companies with broken cap tables

Giffon's top opportunity: venture-backed companies doing $10M revenue growing 30% but that raised $40-50M, so the pref stack means neither founder nor VC will make money. The business is fine; the cap table is broken. Restructure it so the founder owns 30% and runs it profitably, and everyone wins.

“So like say the founder owns 10% and, you know, the pref stack is $50 million, turn it into a business where they own 30% and they can run it profitably and it can be like a great business. Like a question that I always ask founders is, What would you do if you just bootstrapped this thing or if you owned the whole thing?”

Steal thisSource venture-backed companies with healthy revenue but unworkable pref stacks, restructure the cap table so the founder is re-incentivized, and buy the fixed business cheap.

Auto-archive your inbox every 24 hours to force fast replies

Giffon notes the most successful people respond instantly, while their VPs take a week. He wrote a Gmail script that archives his email every 24 hours so he's forced to respond or it disappears, nudging him to fire off quick replies.

“And I really try and force myself to respond fast. I wrote this little script for Gmail that it archives my email every 24 hours. So I like have to respond or it just disappears. And I feel like it's a really good nudge of like, just send the simpler text messages like response.”

Steal thisAuto-archive your inbox daily so unanswered email vanishes, forcing you to reply immediately like the billionaires do.

Silicon Valley founders secretly envy liquid New York hedge fund cash

Giffon argues cash flow beats net worth: behind closed doors, Silicon Valley founders envy New York hedge fund guys who may be less rich on paper but make so much liquid cash it's a different game. A fixed lump-sum net worth feels finite, while recurring income feels free.

“A very funny thing is like all the Silicon Valley guys are really, when like behind closed doors, are really envious of the New York hedge fund guys because they're so liquid. Like they might not actually be as rich per se, but they're so, they make so much cash that it's like it may as well be a whole different thing.”

Net worth is a state of mind; cash flow is the real metric

Giffon's reframe: a finite lump-sum net worth psychologically feels like you're spending down a fixed pile, even if it's huge, whereas recurring monthly cash flow makes you feel free. He says it's more instructive to think about money as cash flow.

“Even if like psychologically, Sam, I know you're big on the money psychology stuff. The idea that you're living off a fixed or finite amount just really changes how you view things, even if it's a ton of money versus this idea of like, I make, you know, whatever, $100,000 a month or whatever. Just the idea that it just comes in.”

Net worth is a state of mind; cash flow is the real metric

Giffon's reframe: a finite lump-sum net worth psychologically feels like you're spending down a fixed pile, even if it's huge, whereas recurring monthly cash flow makes you feel free. He says it's more instructive to think about money as cash flow.

“Even if like psychologically, Sam, I know you're big on the money psychology stuff. The idea that you're living off a fixed or finite amount just really changes how you view things, even if it's a ton of money versus this idea of like, I make, you know, whatever, $100,000 a month or whatever. Just the idea that it just comes in.”

The real first step to building a holdco: own a cash-spewing business first

Giffon's answer to everyone asking how to build a Tiny-style holdco: you can't start with the acquisitions. First bootstrap a business throwing off millions in free cash flow, then the buying part is the easy part.

“And the first step is like, well, you know, bootstrap a business that makes millions of dollars of free cash flow and then like get back to me. The rest is like pretty easy. And that's the first start.”

Steal thisBefore chasing a holdco, build one boring cash-cow business whose free cash flow funds every acquisition.

Start with a concrete deal, not an abstract fund

Giffon argues it's far better to raise around one specific company you want to buy (for Tiny it was Dribbble) than to pitch an abstract holding company or fund. The concrete target becomes the jumping-off point.

“I think it's always so much better to have that than to kind of be like abstractly, oh, I'm going to start a fund, or I'm going to start a holding company, or whatever.”

Steal thisWhen raising, anchor the pitch to one real, nameable deal you want to do rather than an abstract mandate.

Tiny's accidental edge: not knowing an LOI was binding

At 19-20, Giffon downloaded LOIs off Legal Depot and fired them out, not realizing that in private equity an LOI is treated as a sturdy commitment. The naivety made Tiny faster and friendlier than seasoned buyers.

“And we didn't realize that, oh, in private equity, an LOI is like a pretty sturdy commitment or whatever. And you know, that was for better and for worse. On one hand, it let us move really fast. On the On the other hand, we learned quite quickly that, okay, you're not supposed to go back on like what you changed in an LOI and that kind of stuff.”

Discounted cash flow models are just comfort blankets

Giffon says Andrew made him build DCFs because investors were 'supposed to,' but he was inventing every assumption. The models exist to make a scary decision feel rigorous, not because they're real.

“And I think it was like so many of these things are just like comfort blankets or whatever. You just like, it makes you, it's a big scary thing that you're doing and it makes you feel better that you have it so you can look at it and be like, yeah, We've modeled this out, you know, but it's like, it's bullshit. You're just, you're just making it up.”

More quantitative analysis means more commoditized analysis

Giffon's point: anyone can learn DCFs in school, so modeling gives no edge against Two Sigma or Jane Street quants. The edge is in first-principles thinking (e.g. estimating Facebook's real growth) rather than spreadsheet precision.

“Also a lot of the quantum stuff is totally commodified, right? So people like know how to do this. You can learn how to do this in school and therefore maybe it's like a useful table stakes thing. But you're not going to get any edge that way because everyone can do it.”

More quantitative analysis means more commoditized analysis

Giffon's point: anyone can learn DCFs in school, so modeling gives no edge against Two Sigma or Jane Street quants. The edge is in first-principles thinking (e.g. estimating Facebook's real growth) rather than spreadsheet precision.

“Also a lot of the quantum stuff is totally commodified, right? So people like know how to do this. You can learn how to do this in school and therefore maybe it's like a useful table stakes thing. But you're not going to get any edge that way because everyone can do it.”

Win deals on terms, not price: be the no-brainer buyer

Tiny was rarely the highest bidder but won deals by offering certainty, honesty, speed and trust. When a seller left for a 25%-higher offer, that offer often proved fake, financed poorly, or slow, so Tiny still got the deal at a no-brainer price.

“And so it's more like, are you able to get a price that's really a no-brainer? At least that's how I look at it, versus I really think I'm smarter than everyone else, I can pay slightly more.”

Steal thisCompete on certainty-to-close, speed, and trust instead of outbidding; let inflated rival offers collapse on their own.

Give partners a 'release valve' for solo deals

In the Tiny partnership, Andrew and Chris shared the holdco but could also pursue investments and businesses on their own. Giffon calls this solo outlet a release valve that stops a partnership from becoming a prison when co-founders have different tastes.

“I think one thing that can really go wrong in partnerships is if it's like you're dedicating your whole life to this thing and everything you do is going to be through it, it can really turn into this prison if you don't share the same taste as your co-founder. And so having this like release valve And being aware of that is really nice.”

Steal thisLet partners pursue some deals solo outside the shared vehicle so differing tastes don't trap anyone.

Float your offer, then go silent (or hit mute)

A negotiating trick Chris taught Giffon: after stating an offer, say nothing, because people start negotiating against themselves to fill the silence. On a call you can even hit mute so they only hear silence while you talk to yourself.

“Like, one great one is it's always best to just kind of, when you float an offer, to just not say anything else. People will immediately start negotiating against themselves.”

Steal thisAfter making an offer, stay silent and let the other side negotiate against themselves.

Negotiation is just who can bear discomfort longer

Giffon's cynical framing of negotiation: it comes down to who can tolerate the uncomfortable silence longer, a tactic you can even use in a retail setting.

“I mean, one, one very cynical way of looking at negotiation, um, is that it's just who can bear to be uncomfortable longer.”

Same side of the table: put the problem across from you both

Instead of sitting across from your counterpart, Giffon reframes negotiation so both parties sit on the same side and the problem (the price gap) sits on the other. This unearths what really matters beyond cash and works in deals and relationships alike.

“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. And the problem can be you want $50 million for the business, I want to pay $20, but it's still this like, okay, this is a problem. Let's work together to figure this out.”

Steal thisReframe any negotiation so you and the other party jointly attack the problem sitting across from both of you.

Ask 'What would need to be true?'

Giffon's favorite negotiating question: to a seller wanting $100M, ask what would need to be true for you to pay $100M, then lay it out. It surfaces hidden sticking points and turns a standoff into collaboration, and works in fundraising and even planning trips.

“My favorite question is what would need to be true? So it's like, okay, you want to sell your business for $100 million. What would need to be true for me to pay $100 million for it? And you can just lay it out, like, like, what would make this a no-brainer?”

Steal thisWhen stuck on a number, ask 'What would need to be true for me to pay that?' and map the answer together.

Cold email is the most asymmetric trade, if you have the goods

Giffon has sent hundreds of cold emails and never gotten a bad response, only no response. Because there's always a scarcity of interesting, talented people, the downside is zero and the upside is huge, especially for students who are switched on.

“I've never got a bad response. It's usually just no response. I don't even remember the non-responses, but the ones that I've got responses from have been amazing, you know. And so I think, I definitely think more people should do it, especially if you're young or you're a student.”

Steal thisCold email impressive people relentlessly, but only after you can deliver real value when they reply.

Flashy founders are almost always a bad sign

Giffon's worst deal came from ignoring red flags out of greed; he says flashiness and behavior like founders asking where to find drugs on night one are tells. When your own experts keep warning you about a seller, you've got deal blinders on.

“Like, someone who's really flashy is almost always a bad sign. All these little things. And, you know, even like in the case of this deal, I introduced the person to a bunch of different friends and, you know, experts, and they were all like, this guy is really something, you know, like, you, I don't really know why you're dealing with this person.”

Steal thisTreat seller flashiness and unanimous warnings from your own advisors as hard stop signals, not noise.

Tiny made 25x selling meal-planning app Mealime

Tiny bought Mealime, a meal-planning app with 4.5M users, in 2018, recouped its money in a couple of years, then sold it to a grocery retailer at a huge revenue multiple for more than 25x its money, its only sale to date.

“And then we sold it, we sold it for, you know, a huge revenue multiple, made a lot of money, you know, excess of 25 times of our money.”

Buying a $10M-revenue business for a $36 cost basis

When a Fortune 500 had to quickly divest an unwanted unit doing $10M of recurring revenue, Tiny bought it for so little they borrowed the whole price and repaid the loan in 3-4 months, plus got a domain worth $1-2M. KPMG listed the cost basis at $36.

“And so it was kind of this like fun little deal of like, can you actually do a business for— can you buy a company for no money down? And, you know, it won't be a business, it will not be a 20x and it's not going to grow for 10 years, but we'll make many multiples of our money on it. And it's fun, like in the actual fund statement that like KPMG does, they have to list the cost. And so the accountants listed as like a $36 cost basis”