Jason Kirby: It sounds like what prevailed is good sound business. I think that's been a common theme across the last several years, even as tons of money were going into random startups in 2021 and similar situation music, everything was going into all these very similar categories that when the tide got pulled out and everyone's kind of left with their pants out, they're just like, the ones that actually had real businesses, real revenue are the ones that are still around today that were able to

Chris Gladwin: Absolutely. Yeah. Yeah. Yeah

Jason Kirby: to weather that storm and maybe down rounds or things of that sort. But speaking of which, given how many rounds you phrased, what would you say was the one where you came in with a certain expectation and then it was the complete opposite of what you actually expected, or if that ever happened?

Chris Gladwin: Well, you know, Music Now, the fundraising we did after the dot com crash confounded me. It was the first time I was in an irrationally conservative market. I had been in an irrationally exuberant funding market in the dot com bubble, you know, where it was just like, these are smart people. These are people with like, they go to the best schools. They're really smart. And yet they were

Jason Kirby: Well, you know, music now, the fun music you did after the dot com crash, confounds...

Chris Gladwin: they were investing at a level that did not make business sense. They were investing in businesses that didn't make sense. And, you know, so that was kind of hard to internalize: there's this level of irrationality by people who make investments for a living, and they were making bad investments. Then we flipped to the other side — after the dot‑com crash — there had been 56 well‑backed companies competing in this little market, and then we had a three‑and‑a‑half‑year period where there was one equity financing in all of those companies. That was MusicNow. We pulled one out. And then it switched to this irrationally conservative market. At the time, MusicNow was growing top‑line revenue 20% month over month. We were killing it. I remember pitching smart investors with great track records and fancy degrees: “I'm growing 20% MoM in a giant market we can own.” And they said, “Yeah, whatever.” That one confounded me for sure.

Chris Gladwin: The other thing that's interesting: if you look at vintage‑year venture returns, when everyone is investing you get the worst returns. When almost no one is investing, the few that get funded are amazing and valuations are low. Investors know this — they can articulate it — yet in years like the last couple, when it's one of those vintages to make money, there just isn't a lot of liquidity in the system from IPOs and M&A, so they can’t fund all the great deals. It’s confounding.

Jason Kirby: Some of the smartest investors I’ve met took chips off the table when things were frothy, then raised when others couldn’t — they’ll probably have the best vintages.

Chris Gladwin: Yeah, for sure they will. Metrics shift year to year — valuation divided by revenue multiples compress or expand. Investing at 5× revenue works out better than 50×. That’s exuberant years versus cautious years.

Jason Kirby: I coach a lot of founders who only lived one cycle and expect 2021 valuations. They see competitors raise $20M at 50× revenue and think they’re worth $100M at $1M ARR. From your experience through a boom and then a bust, how did you structure your funding rounds and think about ownership and terms?

Chris Gladwin: You want the best deal you can get, but I've always shied away from taking too much money at too high a valuation in exuberant years. If you take a $1B round at a $5B pre‑money with no revenue, at some point you must deliver on that number. If you lock in a crazy share price, a couple of years later when things normalize you’ll be raising at rational numbers — that forces a down round, anti‑dilution kicks in, common gets crushed, founders might get replaced. People also lock in too high a burn. They hire 500 people and start chewing through cash. The more you pour people and expense into a company, the less efficient it gets. Oversizing valuation or burn causes problems down the road. We focus on capital efficiency — get the same done with far less expense. That always helps.

Jason Kirby: Have you had to face down rounds?

Chris Gladwin: I've never done a down round — mainly because, when markets are frothy, I don’t lock in a crazy price. Even in 2021, I could have gone to second‑ or third‑tier investors for a higher valuation. Instead, I stayed in the high end of a good price with professional investors. It’s better to be fair than to get irrational. Eventually things rationalize and that hurts the founder and team if you’ve set the bar too high.

Jason Kirby: Any framework to find that good price range?

Chris Gladwin: Ask investors. VCs and underwriters have models for valuing companies: valuation-to-revenue, valuation-to-ARR, growth‑rate correlations by category. For enterprise software, there’s a well‑established model. Understand how early stage, growth stage, and IPO investors value, then run your business to those templates — expenses as a percent of revenue, target growth, margins. Hundreds of similar companies have come before; learn from them.

Jason Kirby: Do you lead on price first or wait for a term sheet? How did you get to 300 investor meetings and manage the process?

Chris Gladwin: I’ve even written my own term sheet to save time when I know the answer from the models. In early stage, with a high‑quality team, big market, and clear differentiation, the valuation range is knowable. Growth‑stage investors are usually a multiple of revenue or ARR. Underwriters tell you IPO frameworks. Don’t get too cute running an auction to push past the rational range. If you lock in too‑high a price or burn, it rarely ends well. Use the answer and save time.

Jason Kirby: I see founders optimizing for price instead of value. They get distracted from building and later accept mediocre exits. Win‑win terms with investors matter — they’re long‑term partners.

Chris Gladwin: You bet.

Chris Gladwin: Right.

Jason Kirby: Switching to exits: what’s the process of getting bought versus selling your company?

Chris Gladwin: It’s better to get bought than to sell. When you’re being bought, the buyer provides the motivation and pays more for strategic value. If you’re trying to sell, you’re pushing — price and terms are weaker. With Cruise Technologies and MusicNow, we sold the companies; with Cleversafe, IBM bought the company — much better outcome.

Jason Kirby: On the sell side — how did you attract buyers? Blast everyone or cherry pick?

Chris Gladwin: With MusicNow, we were growing 20% month to month, but the investment market had stopped. We had to sell — growth costs cash. In a rational time that business could’ve gone multi‑billion with investor support. We ran a process: contact potential buyers with a package. Circuit City was a candidate — at the time they were in Good to Great and on top of the world. We also powered Best Buy’s download store, and our launch was on the cover of Best Buy’s Sunday circular to ~50M homes. One of those homes was Circuit City’s CEO. He’d seen our buy package that week, then saw the circular powered by MusicNow. Monday he called and said, “Buy that company.” Fortunate timing, but also the result of executing and PR.

Jason Kirby: I love that — you turned a need‑to‑sell into getting bought by showing up where the decision‑maker already pays attention. PR can reframe the narrative so acquirers feel like they “found” you.

Jason Kirby: As we wrap, what advice would you give founders navigating capital strategy and trying to get hundreds of investor meetings?

Chris Gladwin: Figure out how to last long enough to succeed. The number‑one reason companies fail is they don’t last long enough. They’re usually right about the value and competitive position, but wrong about how long it takes. You might think three years — it’s four. If you run out of money, it’s over. Plan to last significantly longer than you think.

Jason Kirby: Incredibly well said. Founders say “we’ll raise next month” or “we’ll hit $10M ARR in six months.” Usually, no. It takes time.

Chris Gladwin: Yeah, it’s gonna take 18 months.

Jason Kirby: Chris, it’s been a pleasure. Steady, level‑headed execution — that’s how you’ve gotten deals done. Where can people learn more?

Chris Gladwin: Simply go to OCNT.com — O‑C‑I‑E‑N‑T dot com. If you need to analyze extraordinarily large amounts of data in a really cost‑efficient way, that’s what we do.

Jason Kirby: Lots of teams are doing that now with AI; data’s the name of the game. You’re in a hot space. Appreciate your time today.

Chris Gladwin: Thanks a lot, Jason. It was a real pleasure.

Jason Kirby: Awesome. All right, go ahead and stop the recording here.