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Jesse Middleton

32 statements across 16 episodes · 13 bullish · 10 bearish · 5 people on the record · first statement Jul 31, 2024 by Jesse Middleton · across every show →

On the record as a speaker too: Jesse Middleton's record, appearances and statements → this page counts the times other people say the name.

Everything said about Jesse Middleton, oldest first

Jul 31, 2024 positive
Disclosure
Middleton wrote first $100k check into Squire after VCs passed
“Squire was the first angel deal I did, and they went and pitched, like, every venture investor, everybody passed, and I wound up writing their first hundred grand into the company”
Jesse Middleton Jul 31, 2024 ▶ 8:07 The Pitch Season 12 Official Trailer: Let's Tear Down the System
Jul 31, 2024 positive
Assertion Not checkable as stated
Middleton: Squire angel investment is at 160x on paper
“They're, that, that's one of my best performing on paper investments. It's at a 160 X my cost basis, but yeah, that's a good one.”
Jesse Middleton Jul 31, 2024 ▶ 9:00 The Pitch Season 12 Official Trailer: Let's Tear Down the System
Aug 14, 2024 bullish
Opinion
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…”
Jesse Middleton Aug 14, 2024 ▶ 24:32 The Secret to Building Wealth for Your Children
Aug 14, 2024 bullish
Opinion
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.”
Jesse Middleton Aug 14, 2024 ▶ 17:28 The Secret to Building Wealth for Your Children
Aug 14, 2024 positive
Insight
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.”
Jesse Middleton Aug 14, 2024 ▶ 21:04 The Secret to Building Wealth for Your Children
Sep 18, 2024 bearish
Opinion
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.”
Jesse Middleton Sep 18, 2024 ▶ 20:50 Bridgei's $1.5M Deal: Transforming Emergency Communication?
Sep 25, 2024 negative
Disclosure
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.”
Jesse Middleton Sep 25, 2024 ▶ 23:01 Can Generative AI Transform Education? Immersion Ed's Bold Pitch
Oct 9, 2024 bearish
Opinion
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…”
Jesse Middleton Oct 9, 2024 ▶ 15:26 $1M Pitch: Can This Beer Startup Transform the Brewing Industry?
Oct 23, 2024 positive
Assertion Supported
Julia Dixon secures $75K in funding from Jesse Middleton and Charles Hudson
“Julia walked out of the pitch room with a 50,000 dollar commitment from Jesse, a 25,000 dollar commitment from Charles”
Josh Muccio Oct 23, 2024 ▶ 25:05 AI in Education Startups: Will This Platform Secure $1 Million Funding?
Nov 13, 2024 positive
Opinion
Middleton: Generative AI observability startups typically hope for only $9K ACV
“Most people in this space are hoping to get 9000.”
Jesse Middleton Nov 13, 2024 ▶ 7:58 AI Needs Feedback Intelligence. Will Chinar’s Pitch Seal the Deal?
Nov 20, 2024 bullish
Disclosure
Jesse Middleton Commits $50,000 to Oma Health
“I would also take a bet on you being able to do this. And so I would be in on this as well. Awesome. Thank you. For how much? So the 50 K.”
Jesse Middleton Nov 20, 2024 ▶ 17:32 Oma Health Shocks Investors—$175K Raised in One Pitch!
Dec 12, 2024 positive
Assertion Not checkable as stated
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.”
Niamh Itza Calvin Dec 12, 2024 ▶ 52:26 Season 12 Finale: What Happened After The Pitch?
Dec 12, 2024 bullish
Opinion
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.”
Jesse Middleton Dec 12, 2024 ▶ 15:56 Season 12 Finale: What Happened After The Pitch?
Mar 5, 2025
Disclosure
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.”
Mike Burton Mar 5, 2025 ▶ 16:06 Bike Theft is a $1B Crisis—Watch This Founder’s $1.5M VC Pitch
Mar 5, 2025
Disclosure
Jesse Middleton: Flybridge typically writes checks of $1M+
“We normally write million plus dollar checks. So I'm going to do the diligence on that check either way.”
Jesse Middleton Mar 5, 2025 ▶ 35:15 Bike Theft is a $1B Crisis—Watch This Founder’s $1.5M VC Pitch
Mar 5, 2025
Disclosure
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…”
Mike Burton Mar 5, 2025 ▶ 6:52 Bike Theft is a $1B Crisis—Watch This Founder’s $1.5M VC Pitch
Mar 5, 2025
Insight
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.”
Jesse Middleton Mar 5, 2025 ▶ 41:44 Bike Theft is a $1B Crisis—Watch This Founder’s $1.5M VC Pitch
Mar 5, 2025 neutral
Disclosure
Flybridge operates a microfund with 50 founder-investors
“We have this microfund strategy where we have a With 50 entrepreneurs and executives that invest on our behalf and with us, and they all have expertise in various areas called next wave.”
Jesse Middleton Mar 5, 2025 ▶ 33:41 Bike Theft is a $1B Crisis—Watch This Founder’s $1.5M VC Pitch
Mar 19, 2025 negative
Opinion
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.”
Jesse Middleton Mar 19, 2025 ▶ 16:05 Will VCs Bet $1.5M on This Luxury Grooming Company’s U.S. Expansion?
Mar 19, 2025 neutral
Disclosure
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.”
Michele Callegari Mar 19, 2025 ▶ 21:04 Will VCs Bet $1.5M on This Luxury Grooming Company’s U.S. Expansion?
Apr 9, 2025 negative
Disclosure
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.”
Jesse Middleton Apr 9, 2025 ▶ 22:09 Aura Finance: Chasing the Ghost of Mint
Apr 23, 2025 negative
Assertion Not checkable as stated
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.”
Josh Muccio Apr 23, 2025 ▶ 26:49 This Startup Solves a Billion-Dollar Problem in Restaurants with AI – Will It Get Funded?
Apr 23, 2025
Insight
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.”
Jesse Middleton Apr 23, 2025 ▶ 23:58 This Startup Solves a Billion-Dollar Problem in Restaurants with AI – Will It Get Funded?
May 7, 2025 positive
Disclosure
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.”
Jesse Middleton May 7, 2025 ▶ 23:52 VCs Offered $2M — Will This Profitable Startup Survive the Pitch?
May 7, 2025 bullish
Disclosure
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.”
Josh Muccio May 7, 2025 ▶ 43:19 VCs Offered $2M — Will This Profitable Startup Survive the Pitch?
May 14, 2025 positive
Disclosure
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.”
Jesse Middleton May 14, 2025 ▶ 30:53 This App Detects Strep from a Selfie…What?!
May 14, 2025 negative
Disclosure
Jesse Middleton passes on Curie DX's current raise structure
“And so I just think that if it changed, we may be interested, but in the current raise, it's probably not a fit for us.”
Jesse Middleton May 14, 2025 ▶ 23:44 This App Detects Strep from a Selfie…What?!
May 14, 2025 bearish
Prediction Not checkable as stated
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.”
Jesse Middleton May 14, 2025 ▶ 28:06 This App Detects Strep from a Selfie…What?!
May 14, 2025
Insight
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.”
Jesse Middleton May 14, 2025 ▶ 27:24 This App Detects Strep from a Selfie…What?!
Sep 17, 2025 negative
Assertion Not checkable as stated
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.”
Josh Muccio Sep 17, 2025 ▶ 28:13 $1.4M Ask: Can AI Fix Dirty Hotel Rooms?
Sep 17, 2025 neutral
Insight
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.”
Jesse Middleton Sep 17, 2025 ▶ 26:01 $1.4M Ask: Can AI Fix Dirty Hotel Rooms?
Sep 17, 2025 bearish
Opinion
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.”
Jesse Middleton Sep 17, 2025 ▶ 18:58 $1.4M Ask: Can AI Fix Dirty Hotel Rooms?
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