Jesse Middleton
General Partner, Flybridge Capital Partners. On 2 shows, 23 appearances. The Shows tab opens the full record on each.
investorfounderexecutiveoperator@srcasm ↗LinkedIn ↗flybridge.com ↗
Jesse Middleton is a General Partner at Flybridge Capital Partners, where he leads early-stage investments in AI applications, developer platforms, and future-of-work companies. Previously, he was an early executive at WeWork, where he co-founded WeWork Labs in 2011.
Everything Jesse Middleton said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Middleton projects CurieDx will make $500K annually, rejecting founder's $6M estimate
“The financial part, she needs to button up, because my math is she'll make 500,000 dollars a year in the next two years, not six million.”
Middleton: Never Accept an Advisor Who Could Be an Investor
“My rule of thumb is don't let anybody be an advisor who can otherwise be an investor.”
Middleton: Big Beer will demand exclusivity or engineer around ReCraft
“I think it's a hard business to imagine, A, it being a standalone business at scale, because he's not making the beer, the big beer company is big beer, would like, they would want this, right, or they're going to find a way to do it themselves, not infringing…”
Middleton: Latin American venture exits lose 20% to 30% to tax friction
“One of the challenges is this like tax and excite, like everything you do there is then effectively costs you 20 or 30% more when you get your money out. So whatever your like goal is, like a billion dollar company is really a seven hundred million dollar comp…”
Middleton: Hotel operators and executives are finicky and hard to sell to
“I worry what the process looks like in selling the operators of hotels. Like I've known many people who've owned and operated hotels. I've known people at the corporate side. They're all finicky.”
Middleton: Object detection on shaky mobile room video is technically difficult
“It's not easy to recognize in shaky video on a cell phone walking around a room if something is out of place.”
Middleton: Founders' biggest grant mistake is taking misaligned funding
“The biggest mistake we've seen founders do is Take grants that don't fit in their existing plan.”
Middleton invested in Vital Audio despite founder rejecting consumer product model
“I invested in Vital Audio because of the show, and I will tell you that he is dead set on going B to B, and I would love for him to offer a consumer version of this product, and he just really doesn't want to do it.”
Middleton: Flybridge commits $50K check to Jungle
“And that's a 50,000 dollar check we can commit into whatever the round is. And I'd like to start by saying, like, I'd like to commit to that.”
Middleton: Founders should never name the first number in negotiations
“I mean, if I'm advising anyone, like sales one-on-one, don't throw out the first number.”
Middleton: None of the four or five HR-selling startups he backed succeeded
“I have backed four or five companies that sell through HR and employee resource groups, and maybe this says more about me than them, but none of them have worked out.”
Middleton: Employers accept $350 annual pricing, but direct consumers will struggle
“I think the employer is comfortable with it, but the consumer probably struggles.”
Middleton: Men Lack Brand Affinity for Beauty Products
“I do have a worry that as men do want to take care of ourselves, like we don't have the same affinity to a beauty brand yet.”
Middleton: Future Money has the best onboarding flow among fintech products
“So your onboarding flow is better than any other fintech product I've ever signed up for.”
Middleton: Generative AI observability startups typically hope for only $9K ACV
“Most people in this space are hoping to get 9000.”
Middleton: Codecademy pivoted to consumers because selling to schools is hard
“Of all the ed tech stuff that we've invested in, you know, Codecademy was one of the larger ones and tried selling in education. It was mostly to consumer, but selling into educational systems is just so hard.”
Middleton: BridgeFi developer adoption is harder than just dropping an SDK
“The developer one seems harder than it would appear on the surface. That, that would be my takeaway on it. That's why I wasn't like an immediate yes, because I don't think it's as simple of a developer platform as like dropping the SDK and go.”
Middleton: Healthcare investments typically demand systemic behavior shifts
“A lot of healthcare investments require you to believe like a systemic change. Like they require a massive shift in behavior and how, what they pay for and infrastructure.”
Middleton: Vital Audio's patents will hold up legally
“I believe the patent will hold up. And so that's part of my, I mean, you have to believe that.”
Middleton: Phil Bearer is best positioned to win family wealth investing
“And so if there's somebody who's going to win in this space, I think it's you.”
Middleton: Founders with a 'reasonable win' return more prepared and driven
“So I think when you have that reasonable win and you're coming at it again, you come really prepared and you come with this feeling that like, I'm going to make a difference, an even bigger difference.”
Middleton: FutureMoney's onboarding is the best I've seen in fintech
“It is super impressive, the onboarding flow, that with only your phone number, it filled out the entire form with my current address and social security number, so your onboarding flow is better than any other fintech product I've ever signed up for, so I will…”
WeWork was conceived as a global entrepreneur network from its inception
“Adam Miguel's vision was always to build a company that was going to be this global professional network of entrepreneurs and small business owners”
The other half of the tape: Jesse Middleton's own voice is left out of every number here. Other people bring the name up 1 time in 1 episode across the shows. 8 statements on the record name them. every mention, with the transcript →
Who brings them up most Harry Stebbings 1
Statements about Jesse Middleton, by other people (8)
Muccio: Jesse Middleton ghosted Science On Call after the pitch
“After the show, two calls and a ghosting. Jessie's the ghost. Jessie, check your email.”
The Pitch Fund commits $100K to Jungle alongside Flybridge's $50K
“The pitch fund is in for a 100,000 alongside Jesse's 50,000 dollar check.”
Callegari: Italian Parent Company Owns 90% of US Entity
“No, it's a new entity owned 90% by the Italian company, 10% by strategic brand investment.”
Burton: Lockstop charges cities a one-time fee per device and provides monthly data
“So now we charge the cities, Because what we're able to do with the cities, Jesse, is they install these devices, and now they get access to those mobility insights that don't exist anywhere else. So we sell into the city, each individual device, we do a one-t…”
Middleton and Fielding pass on Levy during post-pitch diligence
“Jesse told Al he wouldn't be moving forward due to scar tissue from other companies in the hospitality space, and Jenny passed in diligence because she didn't see a repeatable go-to-market strategy.”
Lockstop: Initial contracts cover 25 devices across two cities
“Right now the two cities that we're working with and will be installing is a hundred K, a hundred, 125 K right around that park. And then the individual contracts right now are for the 25 devices with the expectation of scale once the data proofs out.”
Flybridge closes and wires $50,000 investment in Vital Audio
“After our due diligence call, in about a week or so, we were able to actually close.”
Every mention by year
tap a year for its mentions
20VC 1
One line per show, most statements first. The link opens Jesse's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
 THE PITCHLEDGER | General Partner, Flybridge Capital Partners | 22 | 30 | — | full record on the Pitch → |
| 20VCLEDGER | General Partner, Flybridge Capital Partners | 1 | 6 | — | full record on 20VC → |