Fundraising from Both Sides of the Table

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Fundraising from Both Sides of the Table

Real Advice from Founders Who’ve Been in the Pitch Room—and on the Other Side

Andrew Chang

Apr 23, 2025

Transcript

Vertical AI Summit - May 22 - more info here

At the Lynx Collective Startup Fundraising Summit, we hosted a candid panel with three people who’ve sat on both sides of the table:

Sanjiv Sanghavi – Co-Founder & CEO of Texture, Former Co-Founder of ClassPass, Former VC at Day One Ventures
Lindsay Kaplan - Co-Founder Chief, Investor at Next Wave NYC
Brett Martin – VC at Charge Ventures, Co-Founder of Kumospace, Former Co-Founder of Switch & Sonar, Adjunct Professor at Columbia

Between them, they’ve raised hundreds of millions as founders—and invested millions more as VCs. In this conversation, they opened up about what actually works when raising money, what founders get wrong, and what they now look for when writing checks themselves.

Below are 9 insights from the session every early-stage founder should take to heart:

1. Revenue Is Your Best Fundraising Strategy—But Optionality Is the Goal

“The best thing you can do is not have to raise.”

At ClassPass Sanjiv raised just $2M over its first four years, then $100M in the next year—after they had revenue. But now, his fundraising mindset has flipped: focus on building the business so the next round isn’t necessary. That freedom creates leverage.

2. Relationships Open Doors

“I’m pretty sure I met you at a bar once…”

Lindsay shared how both lead investors in Chief’s seed round were people she or her co-founder already knew. One connection came from a half-remembered night at a concert. The lesson? Go to events, meet people, and build weak ties that become strong ones—you never know which one becomes a check.

3. Create Urgency

“You have to create urgency. Make investors feel like the train is leaving the station.”

If you don’t have traction or connections, you need a forcing function. Brett recommended using timed launches, product updates, or even artificial deadlines to create FOMO. Just floating around saying “I’m raising” for six months rarely works.

4. Pre-Pitch Investors Before You Fundraise

“We closed our first round the day we incorporated.”

Before launching his new company, Sanjiv met with every investor he could find who was writing or talking about energy software. Weeks later, when he formally pitched, the round came together fast—because those conversations had already seeded interest and belief.

5. VC Want To Hear Your Secrets

“Restaurants using pen and paper? That’s not a secret. That’s a cliché.”

Brett emphasized that VCs are hunting for secrets—an insight into a problem that others haven’t spotted or don’t understand deeply. Your pitch should teach them something they didn’t know about the market. That’s what makes it investable.

6. Founders Are Dream-Sellers. Investors Are Dream-Skeptics.

“As a founder, your job is to make people believe. As a VC, your job is to poke holes.”

Lindsay summed up the mental shift between being a founder and an investor. You need to be both inspiring and ruthlessly focused. Be the kind of founder who can weave a compelling vision—and still say no to distractions.

7. Stop Trying to Convince the Wrong VCs

“Don’t waste your time persuading someone the idea is good. Find the one who already believes—and convince them you’re the one to build it.”

You don’t need every VC to get it. You just need one who already believes in the market or problem you’re tackling. Save your energy for conviction, not conversion.

8. Talk Market First, Product Second

“I’m not your customer. I want to hear about the market and competitors”

Early-stage founders often spend 80% of a pitch on their product. Big mistake. VCs want to understand the market, how large it is, what your wedge is, and why you will win. The product is a small piece of a much bigger story.

9. Start Your Deck with Proof and How You’ll Raise the Next Round

“Slide one should show you meet the bar for seed. Slide two should show how we both get rich.”

Brett laid it out: if you’re raising a $2–3M seed round in NYC, you likely need ~$250–500K ARR, an in-market product, and the beginnings of a real team. Show that immediately. Then focus your deck on how that capital gets you to a Series A. That’s what investors need to believe.