Robert Wolfe is the co-founder of Zeck, a cloud-based software platform that is reimagining the board meeting. Robert co-founded the company alongside his brother, Jeffrey Wolfe, and award-winning actor and serial entrepreneur Edward Norton.
Zeck raised a $7.5M seed round led by Salesforce Ventures, with participation from Khosla Ventures, Breyer Capital, and Brian Sheth, co-founder of Vista Equity Partners and Haveli Investments.
Before founding Zeck, brothers Robert and Jeffrey co-founded Moosejaw, an outdoor apparel marketplace that was acquired by Walmart, and CrowdRise, a fundraising platform that was acquired by GoFundMe. Robert sat down with Carta to share insights he gained across starting multiple companies, about managing your board, raising money, and setting goals.
Highlights:
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A pitch that doesn’t ‘bury the lede’
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The importance of being fast
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Fundraising as a numbers game
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Setting goals within your bandwidth
CARTA: How was the idea for Zeck born?
ROBERT WOLFE: We built Zeck based on our own life experiences. I’d been a co-founder of two companies before Zeck, and as challenging as every part of the business was, there was nothing more stressful to me than the board meeting. And we weren't particularly good at it.
Our board process at both of our companies was as follows: Our leadership team would go pencils down for 100+ hours to build our presentations. We would send a PDF to our board that they couldn't read on their phone, nor could they engage with it in any way. The worst part was we would all get ready for our grandiose board meeting and we'd meet in New York or LA, only to get into the room and I would reread the board deck that they had already read. The process, from start to finish, was mostly a waste of everyone’s time.
I genuinely thought that we were the only ones who were bad at it. It wasn't until after our companies were acquired, when we got out in the world, that we realized this angst was universal.
And then, the moment the idea sparked: I was on a trip with my co-founders, my brother, and Edward Norton. I had to leave the group to go to a (virtual) board meeting. I came back a few hours later and said, “That was the worst three hours of my life. Edward, do you remember that scene in Fight Club where you were punching yourself in the face? I feel like that's how everyone around the table felt.” We all started talking and said, okay, this pain is real. Everyone gets it. Let's try to figure out a way to solve it.
What has the fundraising process for Zeck been like so far? How did your experience as a serial entrepreneur shape your approach?
We raised money a lot earlier at Zeck than at our previous companies. At Moosejaw we grew organically, and we didn't raise money until we were over 15 years into the business. We also bootstrapped CrowdRise. Before we raised money, we wanted to prove that we could be profitable in a space where most companies had a hard time making that happen.
We thought that Zeck called for something different. We wanted to have great systems in place from the get go for building the product and going to market and do it all responsibly. So, for the first time, we raised money pre-product.
I'm a big believer in luck. And as luck would have it, there were a lot of experienced entrepreneurs sitting around the table when I got back from that miserable, three hour, Fight Club punch-yourself-in-the-face board meeting. One of them was Brian Sheth, the former president of Vista Private Equity. Another was James Zubok, who was also at Vista and is a world class SaaS bada—. Both of ‘em came on as early investors and James sits on our Zeck board. Lucky.
When you get people like Brian and James to believe in the vision, the dominoes fall (in a good way) and we were able to fill out that initial funding round. While fundraising is always hard, having such an incredible and notable group on our side helped us get a lot of momentum.
After we raised that pre-product round, we sat down as a group and decided on very specific goals. We said, okay if we hit these thresholds, then we can say there’s a real market here, and then we’ll go out and do a proper Seed round.
We used Carta for all of this, by the way. We are massive fans of Carta. We've been using Carta since the eShares days and it’s been a key part of so many of our processes. I would never go back to the pre-Carta, excel cap table, painful votes, etc.
Okay, we hit the goals that we set collaboratively with our investors and then went through the same process again. Let’s set new targets and, if we hit ‘em, let's do another round. We completed a Seed round and then last year an A. Our lead investors for that A round were Salesforce Ventures and Khosla Ventures, with Breyer Capital also investing. We have this awesome list of backers, and the best part is they've all lived the problem we're trying to solve. It was really great to be able to speak to their pain points and, ultimately, get their stamps of approval.
What advice would you give founders raising for the first time?
A few thoughts, all of it learned by failing a thousand times.
First, is to not bury the lede in your presentation. During the time between my first two companies and starting Zeck, I advised other companies, so I’ve seen hundreds of pitch decks. Out of a hundred decks, maybe one of them will explicitly say on page one, “This is what’s in it for you, the investor.”
Usually page one is an about page, and it’s sometimes even tough to find meaningful financials in a pitch, on any slide. Or even to figure out what the founding team actually wants to do with the money raised.
Page one should say something like “Here’s why you, the investor, should care.” We were very explicit about that in our own fundraising pitch.
Next is speed. We were quick to answer questions, to do follow-up calls, and to give additional information. Beyond fundraising, from the early Moosejaw days, we’ve always had the mindset that it's hard to always be the smartest; it's not hard to be the fastest. And that's where we've always ‘hung our hat’. We go really really fast with everything that we do.
Finally, fundraising is often a numbers game. I once mentored a company that, when they first told me about their process, they were reaching out to one or two VCs at a time, and I said, well, you're f—--- crazy. If you're going to convert at 1% or 5%, you have to hit a hundred VCs in the next week. Even if you have an amazing business, it’s going to convert at some percentage, which is usually in the single digits. To think that you can hit up five potential fundraisers total and it's going to work, that's probably living in fantasy-land a little bit.
Once investors come on board, how do you best navigate that relationship?
Most importantly, we try to be phenomenal communicators.
Over the years, I’ve had both amazing as well as some pretty terrible experiences with investors and board members. I remember at CrowdRise we were really worried about being in the business of reporting to our investors, instead of running our company. But then one of our investors said to us, “I will never ask you for a report that you shouldn't already have.” And he was right. He was awesome, and that same investor is working with us again at Zeck.
We have certain pieces of data, information, and reports that help us run the business, and we make an effort to surface that information to our investors, get their feedback, collaborate with them, and ask them for help. We do this either every other month or monthly, depending on the stage of the company.
And then for our board, it's the same, plus more. We’re in even more touch with them because they are amazing strategic advisors and mentors. At Zeck, I talk to our board members multiple times a week. These aren’t just people who we have to get in touch with every quarter. Our team is deeply into the grind of the business. That’s awesome for us. Lucky.
My advice to other founders is 1). To probably not take any of my advice and 2). To come up with systems that make communicating with your board easy. Otherwise, staying in touch, which is most certainly to your benefit, can just fall off your list.
Zeck makes that process crazy efficient. With Zeck, for both your investor updates as well as your board meetings, you sync the data that you’re already using to run your business, click one button to visualize that data and then click another button to turn it into your narrative. It's actually pretty mind blowing.
You spoke earlier about having certain metrics that you wanted to hit between rounds. Can you talk a little bit more about how you and your board determined those goals?
Yes, we always work collaboratively with our board to set goals. I really only know about Michigan football. The fact that I can likely name our offensive line from 1997 is probably a little pathetic. But, our board knows the software space like I know Michigan football. We can ask ‘em a question and they’ll just know the answer. Way better than ChatGPT.
So, our leadership team and our board work together to establish targets. It’s always a metric-driven and bottoms-up approach. We always want to be certain that our resources match our goals. And if they don't, then either the goals need to change, or you need more resources -no simply just believing in magic. Although David Blaine is a Zeck investor, which is sort of cool.
