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When it comes to fundraising, the stakes are high. You're not just selling an idea; you're inviting investors to believe in your vision, your team, and your ability to deliver results. But as serial entrepreneur, investor, and advisor Aaron Schwartz shared on our newest episode of Unfinished Business, perhaps the secret to mastering the art of pitching lies in another equally tricky endeavor — dating.
Welcome to Unfinished Business, the podcast where we dig into the whys, hows, and WTFs of building and thriving in business — hosted by longtime founder friends Alex Schinasi and Lee Rotenberg. Every week, we’ll invite industry leaders and fellow entrepreneurs to candidly share their wins, truths, and lessons (and laugh while doing it).
If you look close enough, finding investors can feel oddly familiar to finding a life partner. There’s the thrill of the pitch, the nerves of a first meeting — the ever-so-delicate “will we or won’t we” dance of it all. You’re at once vetting each other, feeling out your competition, and trying to channel your most authentic self.
It’s exhausting and confusing — so consider this guide to pitch clarity. With real-world stories, humor, and a heavy dose of hindsight, we walk through Aaron’s top strategies for securing a successful round — from nailing the first impression to knowing when to walk away. Take notes, pay close attention, then go seal your next deal.
Strong relationships start with a strong first impression, that instant spark of confidence that you may be onto something together. In an initial pitch, you’re sharing the story of your business in order to illustrate its inevitability and undeniable value. But you can’t just talk sweet to investors and call it a day — Aaron stresses that investors want to hear your vision, but they need to know you can deliver on the details. A clear, deep, and clearly deep understanding of your business is critical to get across.
How do you practice? “You should be able to have an aside conversation that shows an absolute mastery of the material,” Aaron explains. Whether it's your product roadmap, market potential, or plans for scaling, being prepared to address any and all questions is critical.
In Aaron’s case, his early success in securing investment for Modify came from knowing his business inside out. He recalls how Steve Etter, a renowned finance professor, backed him because of his in-depth knowledge. Just like a good date, a successful pitch exudes confidence, clarity, and a strong sense of direction.
Time to start talking into your mirror.
Fundraising requires pacing and endurance — too many meetings packed into a short timeframe can hurt more than help. Just think: Would you really quadruple text after the first date? Though it feels counterintuitive, rushing through your raise without holding time to reflect, refine your pitch, and adjust based on feedback can lead to repeated rejections. The last thing you want to do is burn through your leads.
Aaron learned this lesson the hard way, through one of his NFX-backed advisees: “We didn't figure it out until literally business day eight of ten, past 50 meetings where people were saying no. And I was like, shit — we're telling the wrong story.”
We know this may differ from what you’ve heard. Founders often feel pressure to create false urgency in hopes of expediting decisions — but Aaron advises against fake deadlines. Much like in other relationships, forced intensity can scare people off. Instead, focus on showing tangible progress. Whether it’s securing a big client or making key hires, let your results do the talking.
It’s a delicate balance between showing interest and coming off too strong. Aaron’s advice? Be selective with follow-ups, and only reach out if you have something new and significant to share — like closing a major deal or securing another term sheet.
“If somebody's dark for a long time... they're probably not interested,” Aaron share candidly. Exceptions are possible, of course. Though rare, even Aaron’s had instances where a fund reconsidered after initially rejecting his pitch for influencer print-on-demand platform Modify. In fundraising, every case is different — and it’s up to your best judgment to discern when it’s okay to press and when to leave it alone.
And if someone’s not responding, even after following up, it’s probably time to move on. You don’t want to chase someone who’s uninterested anyway — focus on those who prioritize your time and energy.
Never forget that fundraising is a two way street. Investors may hold the purse strings, but you have the final say — and there are some red flags you should never ignore. After all, you’re about to enter into a long-term relationship.
Steer clear of investors who practice ethics that give you pause, try explaining your business to you, or dominate conversations without batting an eye. Aaron recalls a meeting where one investor spoke for 70% of the time — something female, BIPOC+, and queer founders know as our daily reality.
When in doubt, remember to lean on your network too. Founders talk, and in today’s climate, a toxic investor doesn’t have half the power they used to. Creating healthy and compatible founder-investor relationships are critical to your success and theirs. You have to win together.
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