Flybridge's General Partner Jesse Middleton on the Keys to Early-Stage Fundraising: Speed, Conviction & Storytelling
And more insights on how to secure a lead investor
We recently held our first Startup Fundraising Summit as a way to offer the collective wisdom of venture investors directly to founders raising their pre-seed or seed stage funding rounds. Our headliner was Jesse Middleton, General Partner at Flybridge Capital, because his advice never misses. He shared killer insight after insight. We’ve included some highlights below - check out the post as well as some clips from the talk.
Flybridge has a strong legacy of investing in what’s next. The firm manages about $1 billion and focuses on writing first checks between $500,000 and $3 million, leading seed rounds to help early stage startups get off the ground. They’re also a prolific participant in pre-seed startups through its vehicles like Next Wave NYC, XFactor Ventures & The Graduate Syndicate. The investment thesis is primarily focused on technical teams working on AI, enterprise software, and developer infrastructure.
Here are some key insight’s from Jesse’s talk - check it out below.
Move Fast and Don’t Wait for the Perfect Lead Investor
For founders raising pre-seed rounds, Jesse’s advice was simple: move fast. It’s crucial to prioritize closing deals quickly and getting believers on board, rather than waiting for the “perfect” lead investor. "Time is your enemy in most startups,” he said, urging founders to focus on getting their product out and proving their thesis. With AI companies like OpenAI and Anthropic launching something new almost weekly, the race is on, and timing can be everything.
He advised that the #1 most important thing to optimize for is speed - closing fast and getting back to building as quickly as possible.
Lay the Groundwork for Future Support
At the seed stage, Jesse had a different #1 priority: finding a lead investor who is in it for the long haul. He recommended that founders ensure that their lead is a fund that continues to support their portfolio companies at subsequent rounds. That demonstrates their conviction and will help pave the way for raising the next round.
Conviction Over Signal
While having a high-profile investor can help your startup’s credibility, Jesse explained that what matters more is finding investors with conviction—those who truly understand your market and are willing to go all in. “Signal does matter, but conviction matters more,” he said, adding that even party rounds, where no one takes the lead but many contribute smaller checks, can work if the investors strongly believe in the founder and their vision.
Every Deal is Different
There’s no standard deal story. Jesse shared two recent deals that illustrate how every investment process is unique. One of the deals took an impressive 18 months to close, as the founder was still employed at another company and wanted to take his time to launch his startup. Flybridge stayed patient, and when the timing was right, they led a $1.275 million round. The key takeaway? There’s no one-size-fits-all approach to raising capital, and founders should be ready for a process that might look different from the stories they hear in the media.
Storytelling and Excitement are Key
One of Jesse’s biggest pieces of advice for founders pitching is to make sure the investor leaves the room excited. “It’s your job to tell me what to get excited about,” he said, emphasizing the importance of storytelling. Founders should make sure they communicate what makes their business special and why an investor should believe in them. Jesse even recommended taking an improv class to sharpen this skill—being able to read the room and build on what resonates with investors can make all the difference.
In the end, Jesse’s advice boiled down to this: move fast, find investors who believe in you, and tell a compelling story that leaves them excited about what you’re building. For early-stage founders, these tips can make the difference between a good pitch and a great one.
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This write-up was a summary of a talk at the Startup Fundraising Summit, which Lynx Collective held for early stage startup founders in New York City. If you learned something new from this post and would like to read more or attend our events, please subscribe to stay in the know.
A few upcoming NYC Founder/Investor Events
B2B Founders Fundraising Dinner
Join fellow B2B founders currently in the fundraising process for an intimate, casual dinner hosted by investors from Bowery Capital, Forum Ventures & Next Wave NYC. This is a relaxed, agenda-free evening designed to foster open conversation, share insights, and connect with peers who are navigating similar challenges. Whether you're looking to swap fundraising strategies or simply unwind with others in the trenches, this dinner offers a supportive space to collaborate and commiserate.
Inside: South Park Commons
South Park Commons is a community of builders & technologists that specializes in helping founders build conviction in an idea - or as they put it "moving from -1 to 0." They believe that good ideas rarely emerge in isolation. As an "anti-incubator," South Park Commons provides a safe space that encourages judgment-free exploration and the development of new ideas. Join us to learn all about it from the NY leadership.
NYC AI Hack Showcase Night
Join us for an "open mic" night where 15-20 founders, engineers, and PMs will showcase their latest AI-driven hacks. Each participant gets 3-5 minutes to demo their project—whether built for work, fun, or as a side hustle—followed by a brief audience Q&A. You can "apply" to share your AI driven hack when you RSVP for the event.
Please only request an invite if you’re certain you can attend, as our events are typically oversubscribed by 2-3x. This helps us ensure more people have the chance to participate. If you are interested in volunteering to help run our events - you can fill out this form.