Best of 2021: Fundraising Advice From 21 Founders

If there’s one thing I’ve learned from interviewing more than 200 startup founders and emerging VC fund founders on How I Raised It it’s that there is no one way to be a founder or to raise capital in today’s market.

But there are some common threads among their stories — whether they’re fundraising for the first time or have experience raising millions of dollars for multiple companies.

Here is a smattering of the top advice from 21 founders I interviewed in 2021.

After the ‘no,’ what matters is what you do next

It’s pretty much a given that founders will hear more ‘no’s than ‘yes’s when it comes to fundraising. Donnel Baird heard 205 of them on his way to funding BlocPower, a climate technology startup that helps consumers save on energy costs. “I never try to parse no’s from VCs,” he says, adding that if the investors don’t understand the market opportunity, it’s often best to just move on.

“It’s about persistence,” says David Rabie, who raised $70 million for hardware company Tovala that sells a smart oven and meal delivery service. “A big piece of being a founder/CEO that's in charge of fundraising is building up the coping mechanisms to deal with hearing ‘no’ over and over and over again, and not letting that get in your way. I think you should learn that every pitch you have is another opportunity to test something a little different, and figure out what's working and what's not working.”

Holding to a strict timeline — and a schedule of 14 virtual investor meetings per day — was key for Isabelle Kenyon when closing her first round of funding — in just 27 days — for weight loss companyCalibrate. It also meant that she heard a lot of ‘no’s. “Take the 'no' and move on,” she says. “Use the 'no' to make your story better and to anticipate questions that people are going to have.”

Michael Kim, founder of Cendana Capital, also understands that no can be a useful response.  “Press people for a fast no,” advises Michael whose fund has $1.4 billion under management at the time we spoke. But when he started raising Cendana’s first fund a decade ago, 99.99% of the people he pitched turned him down. Worse than the rejections, he says, is the radio silence after a pitch meeting. “This happens all the time, which is why it’s important to ask people for a fast no. You want to suss out how that person you’re pitching really feels because you have to really catalyze something, which takes a lot of time and effort.”

Moving on after no will save you time in the long run. Zuleyka Strasner, the solo founder behind zero-waste grocery delivery service Zero Grocery says she kept at it with investors who ultimately were not the right fit. Sometimes, “the honest answer is: They're just not that into you.” she says. “They're just not that into your company. And if I had learned that, I probably could have gone to 463 meetings in four months instead of 263.”

💰 Bottom line: In fundraising, no can be a useful tool for getting to yes.

Build a full-stack dream team

Kevin Bennett of auto loan refinance startup Caribou (originally MotoRefi) says it’s important to focus on building the strongest team possible, which includes not only your employees but also board members and investors who reflect your values.

For Kevin, working with the Gaingels LGBTQ-focused angel investors was one way to have the company’s values represented in the cap table. When looking for the right investors, he says, “build yourself a framework and think about not just dollars,” noting the other things investors can help with, like introductions.

Remember that you’re making a long-term commitment. “The advice I was given when I raised in my 20s for [stock video platform] Storyblocks was that a financial partner is like a spouse that you cannot divorce,” says Joel Holland, who purchased RV membership program Harvest Hosts in 2018 and went on to sign a $37 million deal with Stripes. “So the advice between the lines was, pick very carefully because you're with this person, this group ‘until death do us part’  — hopefully, a transaction and not a liquidation,” advises Joel. “It's not just the firm you choose — the partner you choose at the firm, that's really what matters because that's who you're going to be spending a lot of time interfacing with.”

VC firms are often more than happy to provide a list of portfolio founders as references, but when Andrew Butt was preparing to sign deals for B2B rebate management platform Enable.com, he went one step further, cold-calling other founders the firm had invested in and asking them about the partner they worked with. He’d probe about the lows especially. “I’ve asked them, have they had bad quarters as well as good ones, and if so, how did the partner behave in those bad quarters? Would they change partners if they went with the same firm again?” he explains in our interview.

For Zero Grocery’s Zuleyka Strasner, building the right team extends to hiring practices, too. "We have many different folks at the table today, very diverse backgrounds, but they have usually been underestimated somewhere in some capacity, or they can draw from that experience,” she says. “Those are the superpowers I want at the table."

💰 Bottom line: Whether its investors or employees, you need to surround yourself with the people who will take your company where you want it to go..

Tap the power of strategic networking

When Domm Holland arrived in the Bay Area from Australia, he had no contacts in the startup world. But by strategically creating a strong network, he raised $124 million for his speedy online checkout platform, Fast, in just two years. “Nothing beats building human networks,” he says.

“That's the way that you're going to get this done in terms of fundraising. But also bear in mind that showing that you can do that is also showing that you can build the business because that's what you've got to do to build a client base, to build a team.”

“Your first big investor isn’t just a check, they will also introduce you to your network,” says Pree Walia, founder of Preemadonna and inventor of the NailBot. Her fundraising kicked into high gear after Jesse Draper of Halogen Ventures invited Pree to pitch on her show, “Meet the Drapers,” then wrote her a check and connected her to other investors.

Adam Cohen-Aslatei found success in going after larger angel networks to find well-connected investors for his innovative online dating app S’More. “Once you have an investor, use that investor to get you other people — use the name brand, if you have a name brand, to leverage for further investment,” he advises.

Cultivate those relationships between fundraising rounds, too, says Lindsay Tjepkema, founder of B2B podcasting app Casted. “There were some people that were cheering us on,” she says, “and then when it came time — even if they weren't a fit, even if it didn't work out, for whatever reason — they were cheering us on, and they were excited to make introductions for us.”

For Christine Tao of online executive coaching platform SoundingBoard, this included investors who said no the first time. She kept in touch with investors who had turned her down, engaging them in conversations about her growing business. “It's a way to be able to continue the relationship,” she says. “It exposes some of your thinking and gives you interactions in a way that I think, especially at that early stage, they really are wanting to see how you're operating and how you're continuing to evolve.”

Network to find mentors, not just investors. As founder Michael Bloch built — and then pivoted — his company, Pillar, he built a network of people who felt invested in the business’s success. “That's why we're here now,” he says, adding that there is huge value in “just being able to find some of those key mentors and guides that have been through this before and are just one or two or three years ahead of where the founder is themselves.”

💰 Bottom line: Always be connecting.

Get your timing right (aka start early!)

Indiegogo founder Slava Rubin regularly coaches new entrepreneurs on planning the next raise, and he put his own advice into action when he set out to raise $6 million for alt investment platform Vincent. “I just dogfooded what I tell others, which is that you typically want to raise when you're about six to nine months out from when you think you might need the money. And I like to think of the raise process as a two-month experience.”

Podchaser’s Bradley Davis found out that waiting until the bank is running dry can send investors the wrong signal. "Start fundraising way, way earlier than you can imagine,” he says. “This is a business. VCs are like, 'they've got three months of runway, they have no other term sheets, let's drain them, let's put them to the very, very bottom, and let's get the terms that we want.' That's how it works. ... I love VCs and investors, but it's certainly business."

“The most unfortunate reason to raise the next round is because you need it, because you're running out of money,” says Phil Libin, founder of Evernote, who recently closed a $100 million Series B on his new video presentation platform, mmhmm. “You really want to avoid that, if possible. So the time to raise a round is when you've made enough progress that you're worth significantly more than you were before.”

Or, forget everything you know about raising in rounds. Instead of fundraising over a set period, Garin Toren, founder of messaging platform ping, has raised $1.9 million by working at it for 3-4 hours each week over a period of two years.

“By having a rolling round, we're able to maximize the value of the company when raising,” he says. “And because we don’t have $1 million in the bank at one time, we've had to be very lean and very conservative. And I would probably be guilty of this — that if I had a bank balance of a million or two, I'd probably spend differently than if I had a bank balance of $300,000.”

💰 Bottom line: Plan ahead and be as strategic as possible when it comes to timing your raise.

Wow investors in the pitch meeting — and before

Be the most impressive thing the investor has seen all year. Between Evernote and mmhmm, Phil Libin worked as a VC at General Catalyst, where he saw about 3,000 pre-vetted pitch queries a year. Maybe 600 of those would get pitch meetings, but only two or three got checks — a typical success rate in early-stage fundraising. “You’re the most impressive thing that I've seen today? Nowhere near good enough,” Phil says. “You're the most impressive thing I've seen this month? Nowhere near good enough. You’ve got to be the most impressive thing I've seen all year, then maybe.”

“Do you have enough chops in you to figure out how to get something to show?” asks Preemadonna’s Pree Walia. The “show and tell” technique was the key to pitching her innovative NailBot to investors. “‘Show and tell’ can happen with a deck, but for me it did not happen with a deck. ‘Show and tell’ for me has always been with an experience, something that someone can physically touch.”

Thomas Fairey ran his fundraising like a sales process but had to flip the script when it came to pitching investors on his esports betting platform Stakester. “The most important lesson I learned about that first round beyond anything, is you are not pitching your product. You are pitching an investment,” he says. “No one cares about your product and how you do what you do. No one cares. All people care about is that they're gonna make a lot of money by investing in you at this stage.”

Developing a habit of outreach can help you land the meeting that will change everything. John Fazio, founder of Nerd Street Gamers, wrote a letter to VC Joe Lonsdale after hearing him interviewed on a podcast. Weeks later, he reached out again, asking for an introduction to someone at Founders Fund — and the connection led to an $11.5 million check

Take it from Jesse Draper, someone who receives countless pitches every week for her fund at Halogen Ventures. Smart founders aren’t afraid to over-introduce themselves, she says. “The greatest thing that happens is when I’ve seen [a pitch] in three different places, and then I speak at a conference and someone comes up and says, I just wanted to put a face to the name. That’s very helpful for me because we see so many faces.”

💰 Bottom line: Use your pitch and outreach to show investors you’re in it to win it — which means a win for them, too.

Nathan Beckord is the CEO of Foundersuite.com which makes software for raising capital. Foundersuite has helped entrepreneurs raise over $3 billion in seed and venture capital since 2016. He also hosts the podcast How I Raised It, a behind-the-scenes look at how startup founders raise money. This article is the third in a series about fundraising hacks.