Bill Boebel is good at seeing things from different angles. As a serial founder who is also an angel investor, he knows the fundraising process on both sides. He’s careful to keep both growth and survival in mind with his companies, spending wisely while keeping them profitable. And he’s able to look at something as common as an organizational chart and envision a company that could reinvent it. “Every company uses org charts, yet there’s no good software for it,” Bill says. “That’s really why we’re doing what we’re doing today.” Bill’s company was just an employee directory at first, but it evolved into a system that allows users to navigate a company’s entire employee infrastructure. Employees can find out who owns which project, and managers can use the software to plan for the future. Pingboard “We’re working on ways to help our clients visualize their companies in their current states, as well as where they’re heading,” Bill says. “They can plan for Q3 hiring and easily communicate that to the whole company, so everyone can know about open positions and how things are going to change.” Bill started the company in 2014, and he has raised three $2.5 million rounds since then. “I call it three separate seed rounds,” he says. The first round was led by , an Austin-based VC firm, and filled out by friends and investors Bill knew from fundraising for his first company, a web mail service acquired by . Bill raised the round before he even had a product to show. But he earned trust through a successful track record and relationships with investors. Silverton Partners Rackspace “I had originally planned on raising a little bit less,” Bill says. “I started talking to Silverton about it, and they convinced me to do it as an equity round. I decided it would be a good idea because they’re very founder-friendly. It set a precedent for strong, founder-friendly terms.” In the end, Bill is glad he went with the $2.5 million Silverton suggested. “Luckily we did, because it took a while to figure out the business,” Bill says. The ‘Touch Zero’ operating model It took Pingboard two years and $2 million of that initial funding to actually figure out what they were doing. But Bill doesn’t usually encourage founders to run through their capital too quickly. “We’re fairly conservative, and we have things we can pull back on,” Bill says. “After that first round, we really needed the additional money. But in the subsequent rounds, we operated in such a way that profitability is always within reach if don’t want to raise another round.” He chases the balance between growth and profitability with his companies, even though it’s not a popular method of fundraising. “I call it a ‘touch zero’ operating model,” Bill says. “We’re going to invest every dollar we can, and we’re going to hit zero in the bank account at some point in the future. But at the same time, we’re designing it profitably, which means we’re in full control of our destiny. If we invest more than that, we’re not in control. If we spend any less than that, we’re not growing as quickly as we can.” The “touch zero” operating method isn’t a one-time setup. Finding the right balance takes consistent attention to your company’s metrics. “Every week, we’re tuning our model based on the prior week’s sales numbers,” says Bill. “Can we turn up the ad spend on Google a little bit? Is it time for that next sales or engineer hire? We’re fine-tuning this thing constantly.” Explosive growth isn’t the only route to VC cash (though it’s the favorite) Bill has a unique understanding of the the investor/entrepreneur relationship. After he sold his first company, he spent some time as an angel investor. He saw plenty of startups discount the idea of entirely. balance So many founders are chasing growth above all else, which Bill calls the “moonshot model.” “It’s amazing how many entrepreneurs I met who didn’t grasp that concept,” Bill says. “They thought the only way to build a startup is to shoot for certain key milestones that make you fundable.” The problem with that method is that the money might not always be there, he says. “They’re basically operating under the assumption that future money is always available,” Bill says. “I’ve seen too many founders get burned by putting themselves in that position. It’s one I never put myself in.” VCs love moonshot companies, but that’s because they’re playing a volume game. Say a firm invests in 10 companies. One blows up, and another one folds because it focused on growth over balance. The VCs might be able to walk away without losing anything. The founder of the company that folds, on the other hand, has to start the entrepreneurial process over again. “I didn’t realize how extreme that kind of moonshot-or-bust mentality is for funds,” Bill says. “I’ve talked in depth about it with some of the partners at the bigger funds, and I totally understand why it is that way.” Bill emphasizes that it’s important for entrepreneurs to find investors who are on the same page about their company’s operating model. “Figure out how you want to operate your company and what type of investor can get behind that,” Bill says. For Bill, like-minded investors have usually been founders themselves. Working with investors who have been entrepreneurs might not be possible for every founder, but Bill says there are plenty of roads to success. “My advice is that there’s plenty of ways to do it,” Bill says. “How you run your company and how you fund your company are things that we, as entrepreneurs, should be able to choose. We can do things a little bit differently than everyone else.” Nathan Beckord is the CEO of Foundersuite.com , a software platform for raising capital and managing investors. Foundersuite has helped entrepreneurs raise over $1 billion in seed and venture capital since 2016. This article is based on an episode of Foundersuite’s How I Raised It podcast , a behind-the-scenes look at how startup founders have raised capital.

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