Sam and Shaan compare notes on their company sale negotiations — Sam sold to HubSpot, Shaan sold and was acquired by Twitch/Amazon — identifying the key mistakes each made: Sam anchored too early by stating a price range, Shaan let daily emotions swing his pitch from cocky confidence to desperate outreach. Both land on the same conclusion: the best negotiating position is genuine indifference to the outcome.
Speakers: Sam Parr (host, sold company to HubSpot), Shaan Puri (host, sold company, got acquired by Twitch/Amazon)
Negotiating Your Company Sale [00:00:00]
Sam: This one comes from Dylan. Dylan asks: how do you negotiate the value of a company you’re selling? How do you come up with the price?
I made a classic mistake: I said the number first. I said: “These companies typically sell for X to Y range — if you’re in the market, let me know.” And of course the first offer they came back with was the low end of that range.
Shaan: Was the final number the high end, at least?
Sam: Somewhere in the middle. Which cost me a lot of money. That one decision probably mattered more than two years of operating the business.
The other thing that compounds it: I sold to HubSpot for their stock. HubSpot was around $350 at the time of the deal. Within weeks it was $550, and a few months later it was $850. So whatever price we negotiated got dramatically revalued immediately after. I still think about that.
After the deal closed, once I was on the same team as the HubSpot person who’d negotiated against me, I did exactly what you should do: I asked her what I did wrong. She confirmed it immediately. You said the number, she said. She latched on like a shark. You get so few reps at selling a company that you should do the post-mortem every single time.
Shaan: I did not say the number first. But I made a different mistake: I let my daily emotions dictate how I ran the sale.
How Emotion Wrecks a Sales Process [00:04:00]
Shaan: I decided to sell in a 45-day window. I time-boxed it — that was good. But I went into it without a consistent approach.
First two days: super confident, almost cocky. My pitch was basically: “Everyone wants us. We’re moving fast. You need to get on the train now or miss it.” That was actually working.
Then someone didn’t reply for two days. Didn’t send the email they said they would. Doubt crept in. And instead of holding the posture, I made desperate outreach to other companies.
The worst example: I reached out to Facebook through a contact and used the word “acqui-hire.” That’s a critical mistake — acqui-hire signals “don’t value my company, just value my talent.” It means a specific, much smaller range of outcomes. I basically told them to low-ball me before they even started.
Luckily the deal chain at a big company is so long that by the time the intro made it to the actual decision-maker, I’d completely changed the narrative. The third person in the chain was asking about acqui-hire and I was like: I have no idea where you got that. And Facebook ended up coming in with the highest offer.
Sam: So you recovered?
Shaan: Recovered, but it could have been fatal. Eventually we got to the point where Amazon was also in the mix — I texted the CEO directly and said: “I’m going to take this other offer unless you can match.” He said, “Give me an hour.” I said I don’t have an hour. He said give me an hour. I gave him the hour. He came back slightly below a match, but they were going to take more of our team and there were other factors that made it the better deal.
Negotiating From Indifference [00:10:00]
Sam: I had a roommate — James — who embodied this. He was an engineer who’d been unemployed for ten months, running up his mom’s credit card. Vungle — Jack Smith’s company — made him an offer for $190,000. He called me and said: “I don’t know if it’s worth my time. I’m going to make them sweat a little.”
I was floored. I said: you have no money. You’ve been unemployed for ten months. You need to take this. He goes: yeah, let’s make them sweat.
Then I get a call from the recruiter at Vungle: “James is a hot engineer right now. We’re not sure we’re going to be able to land him — he’s bargaining so hard.” I covered the phone and told James: you better come to an agreement soon. Then I told the recruiter: just give him what he wants. They upped the offer and he took it.
He negotiated from a place of genuinely not caring — and it worked. The key is actually being willing to walk away, not just performing like you are.
Shaan: That’s exactly how I approached selling. I was totally okay if nobody bought the company. I was kind of excited about just ending it and doing something completely different. If I got zero dollars, I was genuinely excited about that path. So I was pretty free.
Sam: I felt that same thing — even though I had a real business with real revenue. I was burned out and done. I just needed out. That indifference gave me some of the same freedom, even though theoretically I had more at stake.
Shaan: The other note: if you’re at a sub-$50 million deal, you probably can’t afford an investment banker who specializes in this. You’re doing it yourself based on instinct and whatever fuzzy advice you can get from mentors. Nobody teaches you how to land the plane. You learn to take off, you learn to fly — and then suddenly you’re pointing down and hoping your instincts are right.
Sam: And the mistakes cost you millions. That one moment of saying the number first cost me more than most of what I did in the final years of running the company.