Reflections & analysis about innovation, technology, startups, investing, healthcare, and more .... with a focus on Minnesota, Land of 10,000 Lakes. Blogging continuously since 2005.

Category: Entrepreneurs

From Bootstrapping a $70M Company to Leading a VC Fund: Lessons for Founders

Twin brothers Rob and Ryan Weber, founding partners of Great North Ventures, have raised two funds and invested in more than 50 startups to date and counting, throughout the Midwest and the rest of the county. Well before that success, however, they were founders themselves of their own ventures, beginning in their 20s, and they learned a lot the hard way in their life as “operators,” a label they proudly wear. From that experience, it’s no surprise they have actionable advice for entrepreneurs in today’s world of AI and fintech. I recently interviewed Rob and Ryan to hear some of the stories they willingly share as hard lessons for founders launching startups today.

We begin with a story from their early bootstrapping days with their startup, Freeze.com , which they founded in Minnesota in the late 1990s. “We raised an angel round of $320,000 in the spring of 2000, just before the dot-com bubble popped,” said Rob. “We were generating around $50k a month in free cashflow from advertising revenue from our prior dot-com publishing business, so we didn’t really feel we needed the cash from the angel round. However, we were excited to bring on a couple of those angel investors as board members to provide us mentorship and guidance.”

In the year after this angel round, Rob and Ryan hired their first dozen employees and were on the verge of launching their core optimization back-end system, which they had been incubating. “Meanwhile, our monthly cashflow began to decline very quickly,” said Rob, “as the majority of our ad revenues came from dot-com startups that had run out of funding. We were down to less than $100,000 in the bank and were losing money every month.”

That led to a particularly mentally difficult period, Rob said. “I remember one week I couldn’t force myself to walk up the stairs to our office, and the anxiety was causing a serious lack of sleep. Luckily, I got help and worked through this very difficult time.” AI illustration depicting Rob Weber dreading to go upstairs to the office

Rob and Ryan’s board – a benefit of that angel round – advised them to reduce their operating costs and conserve cash to weather the storm. “At age 21, my brother and I had to let go a third of those first employees. It was first time we’d ever had to experience a layoff. It was hard.” However, the pair managed to launch their back-end system, and pretty quickly start to generate significantly more free cashflow with the help of their remaining team.

They were definitely back on track. “By 2005, we had scaled to $30 million in annual revenue and $5 million in EBITDA,” said Rob. I asked him what were the hard lessons he and his brother took away from that very difficult early period.

“Number one, raise cash when you don’t know if you need it,” he said. “It will be easier to do and you never know what the future will bring to your business. And, two, remember your business doesn’t define who you are. Founders sometimes lose track of this because they commit so much energy to their business.”

Because Rob and Ryan have lived the founder’s journey literally from a cold start (pun intended), and now evaluate founders for a living, they have more valuable lessons they can share to help today’s founders. The ones from the early days are especially instructive, as founders who bootstrap successfully for survival often are the ones that VCs find the most promising to fund.

Profitability Isn’t Optional, and Metrics Are Critical

Moving from survival to profitability was a journey the brothers obviously conquered. “When we were just starting out, we had pretty good aggregate metrics for our web traffic, such as how much traffic we were getting each day, from which search terms, and so forth,” said Rob. “But we had no idea how the traffic was converting and contributing to our revenue generation.” Once he and Ryan launched their optimization system, they had much better granularity as to how traffic was converting. “That allowed us to run experiments and optimize for efficiency,” said Rob. “The vast majority of our competitors had no such optimization system, so our revenue and free cashflow started to soar.”

This focus on metrics remains essential for startups today, the brothers point out. “Most lack granular KPI measurement for their businesses, which causes them to make decisions based on intuition alone,” said Ryan. “And that does not scale well.”

There’s a problem with the “growth-at-all-costs” mindset of many venture-backed companies, Rob points out. “Such heavily funded companies can get by with a poorer understanding of the KPIs that drive their business. Even though they operate inefficiently, they can continue to afford to burn lots of cash.” The key takeaway here is that founders mustbuild a fundamentally sound business first, Rob maintains. “Capital should amplify a great business, not create a temporary one.”

The Unfair Advantage of Technical DNA

Both Rob and Ryan studied computer science in college. They didn’t do coding or design work themselves once they launched their startup, “but we were very active and curious about how our team was developing our core systems,” said Rob, “and very involved in product design decisions.”

Ryan added: “Our background studying math and computer science caused us to take a pragmatic, analytical approach to decision making. I also think our technical background made us more relatable across our team. We always placed a high degree of value on technical roles, whereas some companies overvalue sales, for example.”

How involved were Rob and Ryan with their team? “We were very much ‘in the trenches’ understanding how our business was growing,” said Rob. “We were able to make effective decisions quickly. What changed over time as we scaled our business was the need to build a team that was also very entrenched in the technology aspects of our business, and to empower them to make decisions.”

The key lesson here for founders, both brothers agree, is that a deep understanding of your technology, product, and market is your most defensible asset. And having a team that also gets that is mandatory.

Scaling with Scarcity Breeds Creativity

Can a lack of resources help drive a founder to seek his or her own solutions? “We didn’t have a large enough engineering team to automate everything, so we would do a lot of tasks ad hoc,” said Rob. “One example was how we scheduled email campaigns to our opt-in email list. Because that list had grown into the millions, we couldn’t schedule one big email campaign because it would crash our email server. So, instead, for about a year in the early days, I had to break up email campaigns into a series of smaller campaigns and set an alarm to remember to check on them and start up new campaigns. This created a lot of interruption in my personal life – which basically didn’t exist! Eventually, we developed better email scheduling tools, but you do what it takes to grow – and we did.”

The brothers ran their startup – by this time named W3i, and later NativeX – with an intense focus on capital efficiency and a culture of ownership. “When others on the team see how you’re willing to accept certain hardships or personal sacrifices in growing your business,” Ryan noted, “it makes them more willing to take that on themselves. Our early team very much all had this founder mindset.”

The lesson for founders is this: Constraints can actually be a good thing. They force you to build a lean, resilient, and resourceful team.

Looking Through the Investor’s Lens: The Great North Ventures Thesis

When the Weber brothers look at a pitch now, they admit they must see past the flashy growth numbers to the underlying unit economics. “In nearly every first call,” said Rob, “I ask how much capital has been invested into the business to get to where they are now. It isn’t so much how much revenue they’re generating relative to what they’ve burned, but, rather, how much have they really accomplished with the capital that’s been invested?”

With their experience, they ask themselves: Is this a real business, or just a story the entrepreneur seeks to fuel with capital? “I once invested a small angel check into a startup that raised a Seed round pre-launch. I remember the startup burned through all the Seed capital and ultimately never even launched their product. This stuck with me. There are many ‘founders’ out there that, even if they were able to successfully raise a Seed round, still would not be able to organize a team to deliver a well-crafted product that solves a real problem.”

What smart investors like the Webers look for are founders who are obsessed with their business model and their unit economics, not just the funding they seek.

“A really good example of what we call ‘Seed-strapping’,” said Rob, “is our portfolio company WithMe, which began in Chicago, whose founder proudly admits he raised the least amount of capital necessary.”

Investing in Founder-Market Fit

How does Great North Ventures evaluate founding teams today? “I’m looking for founders who have uncovered a market tailwind that is being underutilized and, as such, have created the opportunity to solve a problem in a new way that wasn’t possible before,” said Rob. “Often, this is through the unleashing of an emerging technology where incumbents are slow to adopt.”

Rob goes on: “When Ryan and I were teenagers, in the mid-to-late ‘90s, Internet usage was exploding and, although there were many people in the world experimenting with web publishing, there was a huge imbalance. That is, the opportunity created by the rapid, widespread adoption of the Internet was far greater than the number of web publishers putting up new websites.”

Ryan adds: “Ideally, the founders we look at have been tinkering with whatever technology they plan to unleash so they have mastered the skills required to properly harness it within their business.”

Essentially, the Weber brothers back founders who have a unique, almost unfair, insight into the problem they’re solving. It’s the “Why you?” question.

“Typically, I see the unique insight coming from one of two areas: technology-driven or market-driven,” said Rob. “Founders who have mastered a new technology can often deploy their skills into any number of vertical markets, which can provide them an advantage over incumbents. Think back to the late ‘90s: no one at giant Walmart was going to take on Jeff Bezos when it came to pioneering in e-commerce, despite Bezos having no retail background. Market-driven insights can be very powerful, too, especially in more complex industries where problems are super obvious outside of the industry. When founders have a more market-driven insight but lack technical skills, that’s okay. But we strongly prefer they have a cofounder or early team member who has strong technical skills to complement them.”

Net-net, the brothers look for evidence that the founders are the only people in the world who can build this specific company.

Investing in Capital Efficiency

It’s helpful to look at how the Weber brothers view a startup’s request for capital. Just a number means little – it’s the strategic plan that matters.

“I’ve often seen that, even when startups are competing in the same market, how they deploy capital is frequently more important than the total capital raised,” said Rob. “I’ll give one example from our portfolio. We have a startup in our portfolio called Inhabitr, which was also originally founded in Chicago (but now in California). It provides an AI-powered platform for B2B furniture procurement. Around the time we led their Seed round, a handful of other competitors raised much larger early funding rounds. While Inhabitr invested in its core AI capabilities and chose to partner with others in the furniture retail space, their competitors invested heavy amounts of capital into developing their own inventory and warehouses. Over time, most of Inhabitr’s competitors significantly underperformed because of this poor deployment of capital.”

The Webers’ bootstrapping background gives then a keen eye for founders who will treat every dollar of investment with the same care they’d treat their own last dollar.

Thus, they look fora clear, credible plan for how their fund’s capital becomes a force multiplier for the founders’ existing resourcefulness.

“One thing we often see,” said Ryan, “is startups burning large amounts of capital to fund their unproven go-to-market strategy. A better approach is to deploy small amounts of capital in the early going to develop expertise in one, scalable market channel. Once they’ve mastered that channel, that’s the time to plow capital into it.”

Conclusion: The Best Founders Think Like Investors

The Webers believe, whether you’re bootstrapping or raising millions, the goal is the same: build a durable, valuable company. They know the best founders are always thinking about the long-term health and defensibility of their business.

What final piece of encouragement would Rob and Ryan add? They jointly advise: “Cultivate an unwavering focus on your customers and the problem you’re solving, and let that guide you in key decisions. The investment you make into systems that allow you to understand your customers at the most granular level will likely be your most profitable investment.”

If you’re a founder building with this mindset, and you’re a fit for Great North Ventures’ investment strategy, Rob and Ryan want to hear from you.

To learn more about Rob and Ryan Weber’s background, check out my prior post here.

———-

Note: This post first appeared on the Great North Ventures website, with my byline, and here’s my bio that appeared with it:

Graeme Thickins is a startup advisor and an investor in Great North Ventures Fund I. He is also an angel investor in two subsequent Great North portfolio companies. He has written previously for and about Great North Ventures and its founders over several years.

 

MN Entrepreneurs and the Fortune 500 – A Look Back to One of My Favorite Posts

graphic showing the state map of Minnesota with the words Fortune 500 over itI’ve been writing about Minnesota startup founders for a long time. I can’t remember the first post I wrote about one — probably sometime in 2006. But I do know I’ve penned innumerable such posts over the years. One of my favorite recurring subjects was Robert Stephens, founder of The Geek Squad. I did a search recently to unearth just how many times I wrote about him. It was twelve! Yes, that many posts about just one of our state’s many successful tech founders! Why?  I guess because he was such a fascinating and quotable guy — and of course because I admired his success. Some of my posts about Robert were lengthy features, while others just mentioned his participation in certain local events. Here’s my list of all those posts.

What does Robert have to do with the Fortune 500? His firm was acquired by one: Best Buy. Which you surely know if you live here. And both firms were, of course, founded right here in Minnesota. The significance of his acquisition cannot be overstated: it became the basis of a massive services business for Best Buy, which continues to this day.

My favorite post about Robert was headlined and dated thusly:

text of the headline of Graeme's favorite post about Robert Stephens

Why does this one stand out for me? Because it isn’t just about one of my favorite founders, but also one of my favorite topics: branding. I re-discovered what a great read it was (if I do say so myself!) when I went back to it after so many years. (Warning, it’s a long one.) The full post is here.

Speaking of Fortune 500 firms here in Minnesota… some years after the above, I wrote a commissioned piece on this topic: “Minnesota Has Long Had a High Per-Capita of Fortune 500s. How’s That Working Out?” I didn’t write about Best Buy in that one, but I did quote at least one other Minnesota founder, whose firm was acquired by a Fortune 500 — for close to a billion dollars.

Recently, I was reminded that I only focused on Twin Cities-based Fortune 500s when I wrote that article. How could I have forgotten an out-state Fortune 500: Fastenal, founded and based in Winona MN to this day.. No, it isn’t a very high-tech company, but what an amazing growth story it has been over the years! The recent passing of its iconic founder and CEO, Bob Kierlin, reminded us all of that. I just posted on LinkedIn about him. Some of his very wise words were included there.

The lesson in all of this? Minnesota grows some great ones!

 

Startup Fundraising – What Works in Minnesota?

100-dollar bills in the snow

No word is uttered more often in startup circles, here or anywhere, than that dastardly F word. More ink is spilled and blather thrown around about it than virtually any other topic in the startup world. Who scored a round this week? Why is raising money so hard? When will we have more funding in our town (state, region)? Blah, blah, blah, and more blah. Multiple media outlets fall all over each other to breathlessly report on any successful VC raise (and even sometimes angel raises) as if it’s the equivalent of being drafted into pro ball or something. And I’m not just talking Minnesota — reporting on fundraising news and tracking the ongoing raises of startups is a veritable global industry unto itself.

Why is the topic so ever-present? Should we really be spending so much time talking and worrying about the process of attracting other people’s money? Or, as many founders might suggest, would you be better off to just shut up and bootstrap, focusing on attracting customers instead?

(Note: This article first appeared at Starting Up North, in two parts, both of which are included here.)

I wanted to probe the minds of a bunch of folks I know and admire here in my home state—founders and investors (many of whom also serve as mentors and advisors), plus some recently successful entrepreneurs— to get insights from their experience, and some useful advice.

What have they learned about raising money here in Minnesota? What works to get a startup going? What doesn’t? What’s realistic? What isn’t? Our objective was to try to help you better understand what really goes on out there behind the scenes, not just what you may hear, or read in various reports and stuffy press releases. And also to maybe break some stereotypes. [In my interviews, I asked the founders a similar set of questions, and of course, a different set of questions for the investors. The viewpoints of each didn’t always align exactly with their peers, but they were all quite forthcoming, for which I’m most grateful – and, hey, we all benefit, right?]

Think Before You Raise

One piece of advice that came up more than once about startup fundraising related to the question of why. “Make sure you really need it,” said Chip Pearson, cofounder of JAMF Software [which was acquired by Vista Equity Partners in late 2017 for… a large number] and now at Bootstrappers.MN. “There seems to be a missing component in people’s thinking regarding funding and business plans. If you don’t have a plan on how you can run your business without funding – albeit slower — then you should really spend the time on that problem and then raise money. The other thing is many people starting out see fundraising as a finish line and not a starting line. At best, fundraising is a distraction. At worst, it becomes the only thing that founders think about.”

This raises the question of, can you generate revenue? “Currently, Minnesota angels like to see traction in the form of revenue or meaningful market validation,” said Sara Russick, cofounder of Gopher Angels and a partner in the Capita3 fund. “They want to know the entrepreneur understands how to sell the product. This is a change from when we launched Gopher Angels in 2012. Then, angels were coming in earlier. Now, there are so many companies to look at, and a limited number of angel investors, so we’ve seen a shift in the stage where they want to come in. This is hard for early entrepreneurs because they need that really early, pre-seed capital. Gopher Angels does follow-on in about one-third of our companies, helping them get through that seed stage.”

One founder’s caveat: “A focus on revenue is the most important thing,” said Markus Mueller, cofounder of FashionBrain.ai, based in Duluth. “However, it’s important to focus on the right revenue — not all revenue is created equal. We coined the term ‘toxic revenue’ for that which is opportunistic and does not really grow the company to being profitable and sustainable. Revenue, yes — but only if it’s generated the right way and secures the future of the company.”

I asked another founder how she feels about focusing on customer revenue instead of raising outside investment. “It’s extremely important to pursue customer revenue right out of the gate,” said Mary Fallon, cofounder of Kidizen. “Outside investment is meant to accelerate the growth of a proven business model. No one will invest in you these days unless you have demonstrated that many customers will pay for your solution, however you define ‘payment’. It needs to be a repeatable interaction. In the ‘either/or’ scenario of this question, it comes down to how much of your business you’re willing to give up to accelerate that growth.”

Warning: Are You Ready?

Dave Russick, cofounder of Gopher Angels, offered this advice to founders: “One, do your own diligence on your future investors. Make sure you find ethical and non-predatory investors. Secondly, make sure you raise enough. Don’t low-ball your funding needs.  Raising takes a lot of time. A founder does not want to have to seek funding every six months. What if you don’t achieve your optimistic projections? And, finally, have a funding strategy. Know what your funding needs may be through the next two or three rounds, and plan accordingly.”

I asked Chip Pearson if founders understand how long it realistically takes to raise a round of angel or VC funding? “Not at all,” he said. “It is a tremendous distraction with a number of levels to it – pitch, term sheet, closing. I was surprised how long it took even with two different, highly capable, experienced CFOs running the process.”

What Fundraising Options Are Founders Pursuing in Minnesota, and Why?

Raising money from Friends & Family. Several I spoke with had something to say about this option. “Many professional investors love to see a friends and family round prior to investing,” said Chip Pearson..” The logic is that founders may not care about losing institutional money, but they don’t want to face a Thanksgiving dinner where they lost their parents’ money.”

Another viewpoint was offered by Jeff Robbins, a partner at Avisen Legal, and founder/organizer of investor group Angel Pollination. “Doesn’t matter. Good investors evaluate an investment potential on the opportunity, the team, and the progress, regardless of how the founders move the ball.”

Several of the founders I talked to for this story raised money from friends and family as their first outside money, including Markus Mueller of FashionBrain; Mary Fallon of Kidizen; and Susan Langer, founder of LiveGiveSave. More from them later.

Seeking out Angel Investors. For most startups, significant funds first come from this source. It’s a big topic here in Minnesota, discussed daily in every corner of our startup community, because, quite simply, it’s how the vast majority of pre-seed and seed-stage startup funding has traditionally happened here in our state.

A favorite question is this one: just how risk-averse are Minnesota angels? Do they deserve the reputation? “For the most part, Minnesota angels are conservative,” said Gopher Angels’ Dave Russick. “There are a handful making bets, but most that do are investing in low dollar amounts to spread the risk.” Gopher Angels now has about 80 members and meets every other month, said Russick, and between 40 and 50 attend a typical meeting, depending on the time of the year. “We live stream and record each meeting. There are usually up to an additional 10 to 15 participating via the live stream or watching the recording after the pitch meeting.”

Dave’s wife, Sara Russick, cofounder of Gopher Angels, has this view: “First, if you’re investing in any startup at all, you’re not risk-averse. Minnesota angels value quality. They’re smart and experienced, and bring an analytical lens to how they invest. They’re not ‘heart and gut’ investors, not chasing the next shiny object. This also means that they’re committed to the success of the startups they invest in. They give lots of time and make meaningful intros—they’re really available to the entrepreneurs.”

What’s the perspective of some of the founders I surveyed for this story regarding angels, and their personal experiences?

Eric Martell, cofounder of a new startup called Pear Commerce, who’s working out of the Osborn 370 startup hub in downtown St. Paul, has had a variety of experiences with angel investors – in both Minnesota and Wisconsin. “My first startup, EatStreet [Madison WI], has raised $49M to date, $45M of which was raised while I was there,” he said. “Those raises spanned regional angels to midwestern VCs to nationwide funds to international funds. Admittedly, I was riding shotgun to my cofounder, Matt Howard, who is still CEO at EatStreet. Locally, I raised $1.5 million from angels to get Gener8tor Minnesota off the ground. This was a great learning experience for both raising local money and also running a micro VC fund. Most recently, Pear Commerce participated in the Brandery startup accelerator and received an investment as part of our participation. We haven’t announced our other funding yet, but watch for some news coming!”

Eric continued: “Here in Minnesota, I’ve raised from both local angels and regional VCs and think both work well. I’ve found angels to have a slightly lower risk tolerance than VCs — which might surprise some people. I have a theory about this: If you’re an angel, unless you’re very fortunate to have investable time and cash to build a true portfolio, you probably will err on the side of more caution because you can’t make the sheer quantity of investments a fund makes — time and cash! If you have three shots in a game of horse, you’re probably not taking any of them from half-court. A fund has a bit more of a luxury to place safer bets — more traction — and take a couple of those half-court shots because, if one goes in, you know you’re going to cover the whole fund. I think the best path to more early-stage fundings in Minnesota is for more funds to supplement the incredible activity of our local angel scene, which I really admire. We need a few more local VCs. But, much love to all the existing local VCs!” [Note: we’re not addressing traditional VC in this article, as we’re focusing on early-stage fundraising.]

Susan Langer, founder of fintech startup LiveGiveSave, based in Red Wing, also found her way to obtaining angel funding: “To date, we’ve raised just shy of $500,000 from family, friends, and a local angel group through two convertible notes. The first note did not mandate conversion to the equity round; the second did.” What worked best for her here in Minnesota? “The community! I was able to build on and network through existing relationships, as well as tap into the growing ecosystem in the Twin Cities metro and Southeast Minnesota. It was a labor of love, as I met with old and new friends to share my vision. Meeting Neela Mollgaard, former executive director of Red Wing Ignite, was a godsend. [Neela is now head of Launch Minnesota, an initiative of the Minnesota Department of Employment and Economic Development.] She connected me with valuable resources, all of whom offered, and continue to offer, measurable support — from mentoring and professional services, to pitch competitions and funding. Four years later, all have contributed to getting us where we are today – a working product in the App Store generating revenue.”

How did Kidizen get to angel funding and ultimately a VC round? “Like many startups, we began with seed money from family and friends and worked contract gigs to make ends meet,” said Mary Fallon, cofounder. “Concurrently, we pursued a few startup competitions, which helped subsidize our bootstrapping and helped us get our name out. Google for Entrepreneurs was one of the competitions that really propelled us down our path. In turn, that helped us raise our first round of convertible debt from angel investors. We followed up with a Series A round led by Origin Ventures in Chicago. We’ll be looking to raise our next round in 2020.”

Markus Mueller of FashionBrain: “Under our previous name (Tryon Media), we did a family and friends round, which obviously was after we had invested our own savings in the company. We then also raised angel funds — about $2 million from 2014 through 2016. Some investors also carry notes with the option to convert to equity.”

What has his experience been with angel investors in the Duluth area? “When I first convinced a few local angels to invest, they opened their networks to help me identify other potential investors. Several of our investors have invested more than once, and a few have more than tripled their initial investment.”

Alternatives: What About Bootstrapping?

I asked some founders how they scraped by early on. Is bootstrapping a viable option? How far can it take you? “We grew my previous company from $3000 pooled from the founders to mid-six-figure revenue per year while we were still students [at UW-Madison],” said Eric Martell of Pear Commerce. “I think timing and opportunity need to line up, and it’s totally possible. But my current company could never exclusively bootstrap to scale. It really depends on what you’re building that determines if that’s a viable path.”

Susan Langer of LiveGiveSave: “Before raising funds from family and friends, Red Wing Port Authority, Southern Minnesota Initiative Foundation, and a small amount from a newly-formed local angel group, my husband and I depleted our emergency and retirement savings. I obtained loans secured by our home and life insurance. In hindsight, I would not have done that with our home, as it created a significant barrier for us when we wanted to get a home equity loan to pay off personal debt.”

Markus Mueller of FashionBrain told me how he bootstrapped: “We started out in a floral-wallpaper adorned former master bedroom and moved out when we were five people, then moved to a 300 square foot office space in Duluth’s Canal Park. We still bootstrap on office space and are actively considering remote work for the entire team and company. We also bootstrapped in other ways. However, it’s wrong to think or assume that bootstrapping can help you avoid fundraising. We bootstrapped to be conscious of the use of funds — not to avoid having to raise funds.”

Mary Fallon, cofounder of Kidizen, which began in 2010, had some great insights: “If you’re choosing the bootstrapping path, you’re willing to take little or no salary while working more hours than you’ve ever worked before. It’s often not a choice but a decision you make based on the passion for your solution paired with a lack of independent wealth. It helps to have a strong support system made up of those who are most affected by this decision, which for me is my family. When Dori, my cofounder, and I started out, we were told that we weren’t your typical startup cofounders. ‘Typical’ meant you were young, male, and willing to sleep on peoples’ couches to circumvent rent or a mortgage. We had husbands and young children and were not in our twenties. We failed many times on our path to now. Bootstrapping is viable, yes – if you can produce strong revenue growth while keeping operating costs low. Then your chances of scaling without outside funds are better.”

Another amazing, more recent story about bootstrapping comes from Mary Kay Ziniewicz, founder of Bus Stop Mamas, which I wrote about here.

Two Different Funding Approaches – One Repeat Tech Entrepreneur

Daren Klum is a Minnesota tech entrepreneur who first cofounded LiquidCool Solutions (formerly known as Hardcore Computer) in 2006, based in Rochester, MN. More recently, he founded Secured2, Minneapolis, a data security company. What did he do differently in those experiences? “In both my startups, we initially followed a similar path. We raised capital from friends, family, and small funds. In the case of LiquidCool, we went the VC route for our Series A and B. At Secured2, we’ve bypassed the dilutive nature of VC. Instead, we’re doing alternative financing to scale the business, working with the largest sell-side M&A firm for software companies in the country.”

What has been his experience finding capital here in Minnesota? “We had tremendous support from friends and family in Minnesota for the early rounds in both my companies. However, the bulk of the $40 million we raised for LiquidCool came from out-of-state sources – in North Dakota, Wisconsin, and California. And most of the $6 million raised so far for Secured2 has also come from out-of-state — Virginia, Ohio, and Michigan. We’ve found larger capital amounts to be very hard to find in Minnesota.”

Klum said he bootstrapped both his companies in the early years. “Without showing a proof of concept and customers, we couldn’t ask anyone to invest. Was bootstrapping a viable option? Yes, I recommend all entrepreneurs bootstrap to minimize the risk for their investors,” he said. “Bootstrapping can replace a seed round if you do it while you have a job. I built my first company this way. I worked a full-time job and, at night in my free time, I would build my new business. Once I had enough built to justify investment, I was able to raise capital and quit my day job.”

How did Klum find and connect with angel investors? “I found all my angel investors through my network of friends, family, and colleagues. As well, I’ve been fortunate to get a couple investments from customers and relationships I built while growing the business.”

How long can a funding round take? “In the early stages, it can go very fast, because you’re generally working with people you know – friends, family, colleagues,” Klum said. “The more time-consuming capital raising comes when you get to your Series A and B rounds. The stakes are higher, there’s more due diligence, more risk, and obviously a lot more capital in play. So, generally, any round past your seed round logically takes more time to land. It can be months or even years to close larger funding amounts. It depends on the type of financing — debt, equity, or convertible.”

How Easy (or Hard) Is It Getting That First Check?

I asked Daren Klum what it was like taking that first investor check. “The first check is always the hardest – it’s usually family, and can be a very sobering experience. Once you take someone’s money, you’re committed and there’s no turning back. I see far too many first-time entrepreneurs take that first check, and then the going gets hard and they quit. Quitting is final. If you quit, you can’t reach success.”

Another viewpoint came from Markus Mueller, the founder of FashionBrain. “Getting the first check wasn’t hard at all — at least it didn’t feel that way. But there was a lot of effort that went into preparing the first pitch deck and engaging potential investors. Pre-work is key — by the entire team. They had my back, as the CEO and key fundraiser. Without their help, I would not have been able to do it. It does not get easier – in fact, I believe it gets harder. So, my advice is to focus and raise money as fast as possible with all effort on fundraising, and then return to driving the company’s business development. I made the mistake to raise funds over more than two years — and I regret the lack of focus the came with that. Know exactly how much money you need — raise exactly that. Don’t oversubscribe by more than 10%, for example. And use the funds to grow your company, to create value. Then, if necessary, raise more money at a higher valuation.”

How hard does Eric Martell of Pear Commerce say it is to get that first investor check? “I think this is a total case-by-case question. It was super hard to get early investors at EatStreet, then easier. I’ve seen companies exactly the opposite. You might have a very compelling vision or track record and get first checks easily, but then need to prove results. Likewise, if you’re a Minnesota tech company doing over $10 million in revenue, you’re flying in some rarified air and are likely to get a ton of love on a larger round.”

Rob Walling is the founder of TinySeed, a startup accelerator designed for bootstrappers. (Previously, he founded Drip, acquired by Minneapolis-based LeadPages, which adopted the Drip name.) I asked him if raising friends and family money is important before looking elsewhere. “Prior funding is less important than how much traction – for example, revenue – a startup has. I’d rather write a check to a founder who is capital efficient enough to make it to revenue without raising any funding.”

Should VC funding be so glorified? When is it the right way to go? “VC funding is simply one way to start a company,” said Rob. “It should not be viewed as a goal or having ‘made it.’ VC funding comes with a pretty major set of drawbacks, and founders should know what they are getting into before signing a deal.”

Can the Crowd Help?

A non-traditional option some have pursued here in Minnesota is crowdfunding. Since Kickstarter entered the national scene several years ago, many founders have tried it or its competitors. But, frankly, only a few startups in Minnesota have had great results. That may be changing. Wes Wierson, cofounder of Rochester startup LEAH Labs, is out to cure cancer in dogs. Here’s what he had to say: “Instead of Kickstarter, where you get a deal on a new tech gadget, the crowdfunding platform we chose—WeFunder—actually gets you equity in the companies you support. It’s been amazing for us. In addition to validating the market through testimonials of angel investors who know we’re building a cool product. and pet owners donating on behalf of their fallen furry friend, it brings much-needed seed investment to our business.”

Traditional VC did not fund Wes’ business early on, after he went through a recent biotech class in the famed Y Combinator accelerator program in Mountain View, California. “I think it’s because they really don’t understand our technical science, and, secondly, they’re more risk-averse than they want you to believe. With equity crowdfunding, we’re able to ignite our business based on the passion of dog owners, and the support of angel investors who understand the high reward market we’re building.”

What’s The Current State of the Minnesota Angel Community?

“When we founded Gopher Angels seven years ago, the angel community was limited to hard-to-find individuals or one angel fund,” said Dave Russick, cofounder. “Gopher Angels was able to provide a home for individuals and micros funds to collaborate on deals, which helped fill the funding gap for seed and early-stage companies. Frankly, there was still a greater need for funding than could be provided by GA. Over the last few years, the funding landscape has improved greatly. There are several new funds available to entrepreneurs, many of whom target specific industries. We also now have active accelerators such as Gener8tor and Techstars Farm to Fork that provide seed funding while helping the companies prepare better for the funding chase. There are also multiple individuals and organizations that are serving to connect founders and investors. We even have some funds such as Urban Innovation that have set up offices in the Twin Cities. In short, the angel investor scene here has changed tremendously and changed for the better!”

Joy Lindsay, partner, Sofia Fund: “I think the angel community in Minnesota is healthy and growing. I’ve been an angel investor for 20 years, and it’s probably the most active I’ve seen during that time. There are many new participants to the angel community. When we raised the original Sofia Fund, we purposely targeted women to join the fund who had never invested in the asset class before. These are people who are not only bringing their money but their expertise and network to engage with companies and help them grow.”

She continued: “Dave and Sara Russick have done an amazing job growing Gopher Angels. I was just at their meeting last week. Again, these angels are smart, engaged individuals from a variety of backgrounds and industries. Many have never invested before, but they join the group and learn from each other. The Minnesota Angel Tax Credit has also been a driver of bringing new people to angel investing. As we all know, investing in startups is very high risk, so anything that can be done to support that activity the better. Minnesota has a rich heritage of giving back. While that has historically meant we are very philanthropic, more and more I also see successful entrepreneurs and corporate executives giving their time and talent to invest in and then to mentor entrepreneurs. Like philanthropy, this work is critically important to the economic growth of the state.”

How does startup attorney Jeff Robbins, who also heads the Angel Pollination investor group, assess the current state of the Minnesota angel community? “I’d say better educated on investing and increasingly not doing so. I would add some color to that – our prime angel community is aging out. They’re moving to warmer climates and investing in funds rather than companies. And the recession has delayed the emergence of next-gen angel investors.”

Is that a clarion call to younger angels out there – time to step up?

Sara Russick of Capita3 (and also a cofounder of Gopher Angels) assesses the current situation thusly: “There are so many awesome entrepreneurs who are working so hard. Many more of them deserve funding than are actually getting it. A small number of angel investors can’t fund them all – it’s that simple. We have tons of resources to help grow the startup community. We need more resources pointed at growing the angel investor community.”

Mary Grove, Minnesota-based partner in Revolution’s Rise of the Rest Fund, sees things in a similar vein: “Minnesota’s startup ecosystem has scaled impressively over the last half-decade. It’s an attractive place to start and scale a company. From the density of Fortune 500s to the talent pool to the capital efficiency of building here. That said, there is still a large gap at the early stage in the funding landscape, especially at the Seed and Series A stage across most sectors.”

What Does the Future Hold for Startups Trying to Raise Capital in Minnesota?

Rob Walling of TinySeed says things look good: “The more Minnesota startups that have success, the more our ecosystem grows. I’ve been in town for three years, and, even during that short time period, I have noticed more events, more startups, and generally more action in our local startup ecosystem.”

Sofia Fund’s Joy Lindsay also likes what she’s seeing. “Raising money for a startup is never easy. But I think there are a few trends in Minnesota that are making it easier. Most of the very early capital invested in startups comes from investors in the general geographic region. We do have an active and growing angel community. But what is also encouraging to me is the growth of new venture funds. In recent years, Capita3, Matchstick Ventures, Great North Labs, The Syndicate Fund, and even funds like the student-run Atland Ventures have all closed new funds to invest in seed and early-stage rounds. These funds didn’t exist five years ago and are actively investing in companies, many of which are based in our state. Then there are funds like Vensana Capital, led by seasoned VC Kirk Nielsen, who recently closed a $225-million fund. Obviously, that capital won’t all go to Minnesota companies, but it’s great to have Kirk based here. We could use more of these large Series A and Series B venture capital funds in our state, but it’s encouraging to see so many new funds starting.”

Joy continued: “One area that excites me is the focus on getting all members of our community interested in entrepreneurship and investing. The Sofia Fund was one of the very first groups to focus on growing the number of women angels, and then investing in women-led companies. Capta3, another local fund, focuses on women-led companies in healthcare. Lunar Startups is a local incubator doing great work to support women, people of color, and other high-potential entrepreneurs. The Aspen Institute, the Center for Economic Inclusion, and the Case Foundation recently held a summit to discuss ‘inclusive investing’. Here in Minnesota, MEDA has provided capital to minority entrepreneurs through its $1 Million Challenge.”

Does attorney Jeff Robbins see things improving? And how do we compare to other states? “Improving over the 2008 recession days? Yes. Minnesota fares well among Midwestern states, and we do have cool companies.”

“The future is bright,’ said Sara Russick. “We’re turning a corner and growing from a nascent entrepreneur ecosystem to one that is being supported from all sides, taking advantage of Minnesota’s awesome people, education, big corporations, and communities. Our state is attracting attention from investors from around the country because they see what’s happening here. As more of our startups begin to mature, we could see the Series A/B gap grow. I hope we see many more Series A and B funds come in to support their growth, and keep our innovation and talent here in Minnesota.”

Mary Grove of the Rise of the Rest Fund provided this perspective: “The good news is, more investors are paying attention and seeking opportunities to establish a local presence here or simply seek out local startups to fund. I believe we’ll continue to see expanded access to capital and the opportunity for more innovative companies to start, and equally importantly, to scale and stay here. Our recent Twin Cities Startup Week was a great example of this trend. I connected with investors and startups alike who had flown in from other cities in the region as well as the coasts to participate. At Revolution’s Rise of the Rest Seed Fund, we’ve invested in six Twin Cities-based companies. I’m proud to be based here and part of the Minnesota entrepreneurial community.”

[Note: The second Rise of the Rest Seed Fund was announced October 28 – another $150 million fund focused on backing entrepreneurs outside traditional coastal hubs.]

Minnesota-Raised Entrepreneur Jeremy Allaire Making Big Bet on Blockchain

(Note: as a followup to my post a while back, So What’s Happening in Bitcoin and Blockchain in Minnesota, I thought it would be interesting to tell you about another Minnesota connection of sorts in the blockchain/crypto world.)

Jeremy Allaire, CEO, Circle

Jeremy Allaire, CEO, Circle Internet Financial. (Photo credit: Getty Images.)

For a serial entrepreneur who got his start right out of college in his home state of Minnesota, Jeremy Allaire has had quite a ride. Soon after graduating from Macalester College in St. Paul, he and brother J.J. founded Allaire Corp, an Internet software tools company. After a couple of years in  Minnesota, the firm migrated to Cambridge MA to take a VC infusion. In 1999, it had a successful IPO and soon after was acquired by rival Macromedia for $360 million. Jeremy served as CTO of that firm for a few years, then in 2003 joined VC firm  General Catalyst Partners as an executive-in-residence.

In 2004, Jeremy founded Brightcove, an online video platform used by many top media and marketing organizations worldwide. There, he raised close to $100 million in four rounds and had a successful IPO in 2012. He still serves as Chairman of the Board of Brightcove.

In 2013, Jeremy announced the launch of Circle, an Internet-based consumer finance company that aims to bring the power and benefits of digital money, such as Bitcoin, to the mainstream. As CEO of Boston-based Circle, Jeremy has raised $135 million in four rounds of VC, including $50 million led by Goldman Sachs.

Fast forward to today, when CNBC ran a story  summarizing an on-air interview it did with Jeremy, wherein he stated, in essence, that all global currencies will become cryptocurrencies. (Emphasis mine.) You read that right! He said every currency in the world, as the article stated, “from the U.S. dollar to the Chinese yuan,” will have its own cryptocurrency version.

“Our view is that all fiat currency will be crypto,” he told CNBC in the interview on Monday, June 18. “It seems inevitable at this point.”

The article describes Circle thusly:

Allaire’s start-up offers a blockchain-powered app that lets people send money to each other for free.  Blockchain is the public ledger of activity that underpins cryptocurrencies like bitcoin.

Circle also has a product that lets users invest in cryptocurrencies like bitcoin and ethereum, and another that facilitates over-the-counter cryptocurrency trading for institutional investors.

Circle is now valued at $3 billion and is backed by U.S. investment bank Goldman Sachs and Chinese internet giant Baidu. The CNBC piece also noted that Circle recently said it wants to introduce a new cryptocurrency pegged to the U.S. dollar, called “USD Coin.”

The idea is to speed up transactions made with dollars by using blockchain technology — which maintains a continuously growing digital record of transactions — and reducing the volatility seen in most cryptocurrencies.

It’s not the first so-called “stablecoin” on the market — other cryptocurrencies backed by fiat have been introduced. The most notable stablecoin is tether, a controversial virtual currency which critics have claimed was used to prop up bitcoin prices last year.

Allaire said that Circle’s U.S. dollar-backed crypto would benefit from coming under stricter regulations. The token is being built within an open-source platform called CENTRE, which Circle hopes will be joined by financial institutions and other firms.

Allaire said that the aim of the USD Coin was to bring mainstream financial processes into the world of cryptocurrencies and blockchain technology.

“Our focus with fiat stablecoins is we really think of it as a core building block for a crypto-native global digital economy,” the article quoted Allaire as saying.

“Our interest is in how do we take all of the tasks involved in the financial industry and move those onto a crypto-native infrastructure.”

The CNBC article also added that Circle is looking to add crypto tokens for the Euro and the British Pound.

Wow, what a story! A long way from his start here in the Twin Cities, but this Minnesota-born entrepreneur isn’t just out to change the world of banking — he’s out to change the very nature of money itself.

Go, Jeremy!

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P.S.  As long as we’re taking a bit of a walk back in history, I’ll link to three other posts I wrote about Jeremy on this blog some years ago, including one lengthy piece entitled “Minnesota Boy Makes Good (Very Good)” — based on an interview of Jeremy at the very seminal PC Forum in 2006. It was the last of an amazing run of those conferences, one that stands out in my mind as the best, most star-studded Internet conference I ever attended. And I attended and reported on plenty!