Last month we had Jesse Middleton (Partner at Flybridge Capital) keynote our semi-annual Startup Fundraising Summit. In his talk, he gave Founders candid advice on how to approach investors, structure rounds and navigate the human side of fundraising. Here are the insights from his talk.
1. Pitch investors who already believe in what you’re building
Fundraising is hard enough without starting from misalignment. Focus on investors who already like your space, stage, and check size. If you’re raising a $2 million pre-seed round, don’t waste time pitching late-stage funds. Use Signal NFX or Crunchbase to build a list of relevant firms. When reaching out, clearly state your round size and why you fit their thesis. Spend time where a “yes” is possible. This might seem like obvious advice, but so many founders spend their energy trying to convince the wrong investors to be interested in their startup.
2. Fundraising is a numbers game, but details matter
You’ll need to reach out to many investors, but quality still matters. Firms share CRMs, so avoid sending the same generic note to every partner. Pick one partner per firm, personalize your outreach, and work in small batches so you can test what resonates. Founders who treat fundraising like a structured process, not random cold emails, close faster.
3. Pay attention to behavior, not words
Judge investor interest by what they do, not what they say. Fast replies, partners joining the next call, and early introductions are good signs. Slow follow-ups and vague praise usually mean low interest (they’re just not that into you!). VCs are polite by nature, so focus on actions over adjectives.
4. Real offers have amount and price
“Interested” isn’t an offer until an investor names both dollars and valuation. Run a tight process so your conversations happen in a short window. When the first real offer lands, tell other firms you’re aiming to finalize within a week or two. Be transparent. Bluffing about investor interest never works because VCs talk.
5. At the earliest stages, only three terms matter
Early fundraising can get lost in unnecessary details. Jesse simplifies it:
check size
price
board composition.
You need a lead who can set terms and take about half the round. Create a founder-controlled board early, it builds habits around reporting, discipline, and equity hygiene. It’s easier to start clean than to fix later.
6. Use AI to personalize, but warm intros still win
AI-written outreach is fine if it’s specific and accurate. Use AI to summarize an investor’s posts and portfolio, then reference that in your message. A thoughtful note gets read; generic spam does not. Still, the strongest intros come from founders already in a VC’s portfolio. They carry trust and context that no AI can replicate.
7. Be cautious with intros from investors who passed
If an investor who fits your stage and category passes and then offers to introduce you to others, that can send a negative signal. Other investors may assume something’s off. Ask if you can share the reason they passed. Context reduces confusion. Prioritize introductions from portfolio founders who use your product or know you instead.
Bonus tip: Master the art of improv
Most investor meetings go off-script. Taking an improv class to get comfortable thinking on your feet. Founders who can handle interruptions, pivot smoothly and keep energy high stand out. Improv teaches you to stay collaborative instead of defensive and that human connection often closes the deal.
The takeaway
Jesse Middleton’s approach to fundraising blends structure and adaptability. Know your audience, run a disciplined process, and control your timeline. Build relationships with investors who already want to believe, and practice staying calm under pressure. Fundraising is equal parts process and performance. Treat it that way, and you’ll raise faster and build stronger partnerships.
