bootstrapping
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When you hire a marketing consultant, you don’t necessarily expect to wind up discussing your life’s purpose. Yet, that is what Spanish marketing expert and entrepreneur Alex Barrera often ends up doing with startup founders who hire him to help improve their pitch. They think they are going to get help convincing investors, and they do, but the byproduct of the process is that they reframe their startup’s vision.
In this context, ethical and philosophical considerations aren’t that far away, because more often than not, this includes a deep look at how their company impacts society. “The days where you could do whatever you wanted and dive into grey legal or moral areas are dwindling,” Barrera says. “Growth companies need to be careful about the potential fallouts of pursuing such strategies. While there are still plenty of investors that push for “growth at any cost,” the social pressure is changing and it’s suddenly becoming costlier to take such stances.”
You may have spotted Barrera’s cowboy hat at one of the many startup conferences he is involved with as a mentor, judge, host or speaker — and he does wear many hats.
Having previously co-founded two startup accelerators and Europe-focused tech publication Tech.eu, he now authors The Aleph Report, a periodical publication on cutting-edge technology and its implications. But it is through his Press42 venture that he collaborates with startups and corporations on organizational storytelling and strategic communications, and it is also what we discussed in the interview below (which has been edited for length and clarity).
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What do people often misunderstand about pitch training?
Well, it depends on their experience level. When first-time entrepreneurs hear about pitching, they immediately think of the infamous “elevator pitch,” roll their eyes and moan. For those with a bit more experience, pitching is about a set of slides to achieve a certain goal, mostly funding. However, seasoned managers end up discovering that telling the story of their product or service is not a one-way street. Having to sell a future vision of where the company is heading invariably affects your conception of the product in the now and what you need to build to achieve it. The vision impacts the product, because you need consistency between the product and storytelling.
What type of companies do you help?
I have been helping startups with pitching for years. This used to be mostly early-stage startups, and in groups, with accelerators and startup competitions calling me to help their entire batch or portfolio. I still provide that sort of training, but these days I will more often work one-on-one with a single client that is at a later stage. And I also sometimes work with tech companies getting ready for M&As, as well as large corporations.
“I don’t work with companies that sell smoke and mirrors or hurt society because they shamelessly disregard any responsibility for their impact on others.”
What is your sweet spot for startups you work with?
For one-on-one work, I have a preference for David versus Goliath, and less sexy spaces. I love these companies that were built without the noise: There’s a lack of hubris, they are really humble, but the numbers are there — the founders could be obnoxious, but it’s the opposite. I don’t work with companies that sell smoke and mirrors or hurt society because they shamelessly disregard any responsibility for their impact on others.
Luckily, that’s rarely the case of people who call me. Usually, they are a bit out of the circuit, and they often have impostor syndrome. So my work is also about helping them understand what they can be proud of what they do, and then how to show that in their pitch. They value talking to someone who understands them and their challenges. I spend a lot of time doing research on all verticals and thinking about the future, so the conversation will typically go like this: “Dude, you get it!”
What is one of your favorite things about one-on-one pitch-related consulting work?
I find it very fulfilling to see how much value it brings to those involved. I am also a developer, and I do project management, but most of the consulting I do is not the kind of growth marketing stuff that takes more time to show results. When you do growth hacking at the product level, it takes time to see the impact, and even then, it’s not always easy to connect the dots.
When we work together on their pitch, CEOs can instantly see if the new pitch resonates or not; and they also know if the exercise itself worked for them. Working on a pitch requires a lot of reflection and it entails a lot of tension between you and the CEO.
This is especially true at the beginning, when you keep questioning why they did this or that, what the product provides and to whom, or why it grew here and not there. All these questions force many founders and managers to stop and think hard about the product, the market or the roadmap. Sometimes it pushes them to provide data to back up certain claims. The process pushes them to revisit old biases, beliefs or even myths around their company. Many people are surprised by how much clarity they gain into their company when they work on a pitch.
Do you only work with founders and executives?
Sometimes, the clarity and the strategic insight that working on a pitch provides to founders or CXOs becomes a trigger for them wanting to provide that level of understanding to other areas of the company, like sales, customer support or even the product team. In my case, being a developer myself enables me to switch and adapt my process to any layer of the organization, including the development team.
This is rare, but it eventually turns me into a kind of translator of the challenges of different parts of an organization, acting ultimately as the connector bridging different perceptions. In the end, that’s exactly what storytelling provides. It’s not just a tool for pitching, it’s a brutally effective way to communicate between humans, especially around challenging topics.
How would you describe the value that executives get from your collaboration?
One of the usual and even surprising values for most executives is the insight the process provides. When someone is running either a big company or a scaleup, their day to day is all about growing. They rarely have time to sit down and think about where they’re heading in terms of future product. They do have a roadmap, and their KPIs, but I rarely see a strong future vision broken down into steps.
The pitching process provides them with two valuable things: time and perception. Time because as they’re paying me, they’re stuck with me and need to allocate time for our sessions. That bubble, and the need to build a coherent story that tells why the company is at that particular point, create tremendous insight for most. And then, there’s perception. It’s funny because they’re the ones that provide all the pieces of the picture, I just help them put them together and then point at the obvious.
This process is very rewarding at a personal level for them. It helps them build a confidence that, while it was always there, it rarely shone through the pitch before. It also makes them reflect on where they want to go next, not just from a product perspective, but from a mission’s perspective. It reconnects them with that side that most of us care about, and the personal questions we ask ourselves about life and meaning.
How do you bridge the gap between what your clients already know and what’s next?
My clients already know how to grow a company. I always keep this in mind, not just with startups, but also with big corporations — too often, I see consultants talking to them and starting by telling: “You are doing it wrong!” Well, they got to where they are, didn’t they? It doesn’t mean that they don’t need help, but you can make them see that, you don’t have to dismiss what they have achieved. I see myself as the person that helps them get to the next level and build on top of what they have already done. Sometimes it takes some bruising to get there, but there is always massive respect for their achievements.
These people are very good professionals. It’s not that they don’t see or can’t see the vision. It’s that the need to connect the dots in detail allows for the emergence of a strategic vision of the organization. Now, here is where the real “coaching” kicks in. When such a picture emerges, many founders or executives tend to shy away from it. They have a hard time believing that they might be onto something groundbreaking or actually winning in their respective markets.
This is especially true for many scaleup companies. They’ve been fighting, first for market fit, and later on for market share, that they freeze at the possibility that they might be doing a fantastic job. Part of my role is precisely to break through their impostor syndrome and encourage them to be bolder, to believe in themselves, to trust the data.
How do you promote your services?
Well, it would be very hard for me to do cold calling. I wouldn’t be able to say: “It’s not just about pitching, you are going to see the future of your company!” — so I stopped even trying to market that. My best marketing tool is word of mouth from my clients, or even from people that see me perform on stage. But even then, people call for help with a specific milestone, like raising a round. It’s only through the process that they see that there’s way more to it. They begin to understand other parts about themselves that either enhance their capacity to raise more funds, or even take them to the next level like an acquisition or the development of a major breakthrough.
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What do you end up actually working on with founders?
Going higher up the chain, the pitch becomes a very powerful tool not just for fundraising, but also for thinking about your company strategically. It’s a place where founders can reach clarity about their strategy and what really matters — questions they don’t have time for on a day-to-day basis. They allocate time to it because they think it will help with fundraising, and then they find out that it helps them understand their company.
So typically, they will call me because they are raising a Series B round, or a very large A round. They realize that to unlock the next milestone, they need to fine-tune what they say. The game is different; it’s not about market fit anymore, or just about gaining market share, and what worked for them just no longer works — especially if they were semi-bootstrapped up to that point. They need to talk to someone who understands them and can help them prepare for the future, for instance by researching certain pitfalls or trends. I’m not just the guy that “pitches” but the guy that’s going to provide you with ammo to help you build a compelling case for your audience, whatever it is. The pitch is just an excuse!
“The thing is, scaleups and growth-stage startups have a choice in how they market themselves; so they need to be aware of ethical concerns that may arise sooner than later.”
What’s your take on comparing your startup to another one when pitching; for instance, calling yourself the “Uber for X”?
Analogies are very powerful. The major challenge when you are pitching any company, even a late-stage one, is that people have a tendency to put you in a box. So you have two options: either you let them do it, or you provide the tools to put you in a box. That’s where analogies work really well.
But then, who do you compare yourself to? It’s a challenge, because two elements are becoming increasingly important: capturing the right trends of the moment, and the ethics of how you do what you do. You want to control which box they place you, ideally one that’s trendy but at the same time one that doesn’t position you in apparently direct competition with someone you don’t want to be associated with.
Why do startups need to be careful when communicating?
Over the last few years, we have seen how startups are no longer seen as innocent by society; they no longer have “carte blanche,” and society is becoming a lot more sensitive. There’s a polarization issue around many topics, and we are increasingly going to see a clash between society and startups. It is even going to increase post-COVID, with tensions around automation versus jobs. And the thing is, scaleups and growth-stage startups have a choice in how they market themselves; so they need to be aware of ethical concerns that may arise sooner than later.
Society is going to ask you for responsibility. What’s happening with big brands is trickling down, and scaleups are hitting that threshold sooner. Typically, it catches them unprepared, because they reach that stage only knowing local feelings about what they do, and suddenly getting national or regional blowback. Or they expand internationally with local operations led by really young people with no experience in dealing with politics, who suddenly face strong local blowback.
All of this has a lot to do with pitching, because it’s not about product anymore. So for instance, it’s about convincing public authorities at different levels to let you operate, when their incentives are very different from investors. It’s B2G2C — business to government to consumer. And we are seeing more and more startups, with regulation as a factor in their operations.
How can you talk to public authorities, customers and investors in a unified pitch?
The major pitch needs to bring all elements together. It needs to be clear on what you do, and hit the right notes on ethical concerns. It’s important both for regulators and for fundraising; because from the investors’ perspective, it also reduces uncertainty around your business. As a scaleup, your ability to scale is a concern, so it helps to show that you are thinking and planning around societal impact.
I have to say that an increasing amount of investors do genuinely care about this. It may be because they have been burned, for instance from seeing regulatory blowback firsthand, or just because they are growing conscious. There are still some investors that have the “Uber mindset” and only care about muscle — grow first, and only then, deal with regulators — but more and more, VCs are aware that this might not fly, because society is changing. The pandemic is just highlighting this even more.
What about startups? Do they also care more about their societal impact?
I think it’s a pendulum, and the current generation is a child of the previous regulatory blowback. Crypto might still be on the other side, but increasingly, startups are aware that there are societal implications they will have to deal with. I also try to bring that message across when I prepare my clients to pitch — and warn that it sometimes happens very quickly: We’ve seen how one prohibition in one place can spread like wildfire. So you need to regulate your initial message and also be prepared to adapt quickly.
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Lower, an Ohio-based home finance platform, announced today it has raised $100 million in a Series A funding round led by Accel.
This round is notable for a number of reasons. First off, it’s a large Series A even by today’s standards. The financing also marks the previously bootstrapped Lower’s first external round of funding in its seven-year history. Lower is also something that is kind of rare these days in the startup world: profitable. Silicon Valley-based Accel has a history of backing profitable, bootstrapped companies, having also led large Series A rounds for the likes of 1Password, Atlassian, Qualtrics, Webflow, Tenable and Galileo (which went on to be acquired by SoFi).
In fact, Galileo founder Clay Wilkes introduced the VC firm to Dan Snyder, Lower’s founder and CEO. The two companies have a few things in common besides being profitable: they were both bootstrapped for years before taking institutional capital and both have headquarters outside of Silicon Valley.
“We were immediately intrigued because Ohio-based Lower echoes both of these themes,” said Accel partner John Locke, who led the firm’s investment in Lower and is taking a seat on the company’s board as part of the investment. “Like Galileo, Lower will be one of the most successful bootstrapped fintech companies globally. The combination of a company built in a nontraditional region across the globe and a bootstrapped company reminds us of [other] companies we have partnered with for a large Series A.”
There were other unnamed participants in the round, but Accel provided the “majority” of the investment, according to Lower.
Snyder co-founded Lower in 2014 with the goal of making the home-buying process simpler for consumers. The company launched with Homeside, its retail brand that Snyder describes as “a tech-leveraged retail mortgage bank” that works with realtors and builders, among others.
In 2018, the company launched the website for Lower, its direct-to-consumer digital lending brand with the mission of making its platform a one-stop shop where consumers can go online to save for a home, obtain or refinance a mortgage and get insurance through its marketplace. This year, it launched the Lower mobile app with a savings account.
Sitting (L to R): Co-founders Dan Snyder, Grayson Hanes
Standing (L to R): Co-founders Mike Baynes, Chris Miller
Not pictured: Robert Tyson; Image credit: Lower
Over the years, Lower has funded billions of dollars in loans and notched an impressive $300 million in revenue in 2020 after doubling revenue every year, according to Snyder.
“Our history is maybe a little atypical of fintech companies today,” he told TechCrunch. “We’ve had a view going back to the start of the company that we wanted to run it profitably. That’s been one of our pillars, so that’s what we’ve done. Also, we all grew up in the mortgage industry, so we saw firsthand the size of the market, but also how broken it was, so we wanted to change it.”
In launching the direct-to-consumer digital lending brand, the company was working to make the homebuying process more “digital, transparent and easier for consumers to access,” Snyder said.
At the same time, the company didn’t want to lose the human touch.
“We tried to design the app flow in a way where you can get as far along as you can in the application but if you want, at any point in time, to talk or chat with someone, we’re available,” Snyder added.
Image Credits: Lower
Lower’s typical customer is the millennial and now Gen Z who’s aspiring to own their first home, according to Snyder.
“They might be thinking, ‘OK, I might be living in an apartment now, but in the next few years I’m going to meet someone and/or have a child and I want to unlock the investment that is a home,’” he told TechCrunch. “And we’ll help them on that journey.”
Lower’s recently launched new app offers a deposit account it’s dubbed “HomeFund.” The interest-bearing, FDIC-insured deposit account offers a 0.75% Annual Percentage Yield and is designed to help consumers save for a home with a “dollar-for-dollar match in rewards” up to the first $1,000 saved, Snyder said.
Lower works with more than 35 major insurance carriers nationally, including Nationwide, Liberty Mutual and Allstate. It has more than 1,600 employees, about half of which are based in Lower’s home state. That’s up from about 650 employees in June of 2020.
Looking ahead, the company plans to add more services and has an “aggressive roadmap” for adding new features to its platform. Today, for example, Lower sells primarily to Fannie Mae and Freddie Mac. And while it services the majority of its loans, like many large lenders, it uses a subservicer. That will change, however, in early 2022, when Lower intends to launch its own native servicing platform.
And while the company intends to continue to run profitably, Snyder said he and his co-founders “think the time is now to gain share.”
“We want to become a global brand, raise money and gain market share,” he added. “We’re going to continue to double down on product and build out our capabilities. We are the best-kept secret in fintech and plan to change that with smart branding, advertising and sponsorships.”
And last but not least, Lower is eyeing the public markets as part of its longer-term roadmap.
“Ultimately, we know we can build a great public company,” Snyder told TechCrunch. “We’re of the scale to be a public company right now, but we’re going to keep our heads down and we’re going to keep building for the next few years and then I think we can be in a spot to be a strong public business.”
Accel’s Locke points out that in the U.S., mortgage and home finance are among the largest financial service markets, and they have primarily been handled by large banks.
“For most consumers, getting a mortgage through these banks continues to be an overly complex, slow-moving process,” Locke told TechCrunch. “We believe by providing consumers a great mobile experience, Lower will gain share from incumbent banks, in the same way that companies like Monzo have in banking or Venmo in payments or Trade Republic and Robinhood in stock trading.”
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The clock begins ticking on a startup the day the doors open. Regardless of a young company’s struggles or success, sooner or later the question of when, how or whether to sell the enterprise presents itself. It’s possibly the biggest question an entrepreneur will face.
For founders who self-funded (bootstrapped) their startup, a boardroom full of additional factors come into play. Some are the same as for investor-funded firms, but many are unique.
Put happiness at the center of the decision, and let your intuition — the instincts that made you the person you are today — be your guide.
After 18 years of bootstrapping a BI software firm into a business that now serves 28,000 companies and three million users in 75 countries, here’s what I’ve learned about myself, my company, about entrepreneurship and about when to grab for that brass ring.
Starting a software company 7,900 miles southwest of Silicon Valley requires some forethought and not a small amount of crazy. When we opened, it didn’t occur to us that one could have an idea and then go knock on someone’s door and ask for money.
Bootstrapping forced us to be a bit more creative about how we would go about building our company. In the early days, it was a distraction to growth, because we were doing other revenue-generating activities like consulting, development work, whatever we could find to keep ourselves afloat while we built Yellowfin. It meant we couldn’t be 100% focused on our idea.
However, it also meant we had to generate income from our new company from Day One — something funded companies don’t have to do. We never got into the mindset that it was okay to burn lots of cash and then cross our fingers and hope that it worked.
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Over the past decade, venture capital has become synonymous with entrepreneurship. Founders from around the world arrive in Silicon Valley with visions of record-setting A rounds and billion-dollar valuations. But what if you don’t have unicorn dreams — or you don’t want to pursue VC money?
Bootstrapping a SaaS company is not only possible — I believe it’s a saner, more sustainable way to build and scale a business. To be clear, bootstrapping isn’t always easy. It requires patience and focus, but the freedom to create a meaningful product, on your terms, is worth more than even the biggest VC check.
The freedom to create a meaningful product, on your terms, is worth more than even the biggest VC check.
I started my company, JotForm, in 2006. We’ve grown steadily from a simple web tool into a product that serves more than 8 million users — without taking a dime in outside funding. We’re profitable in an industry with big-name competitors like Google.
Most importantly, I still love this company and its mission, and I want the same for my fellow entrepreneurs. If you’re a SaaS founder who’s wary of VC funding, here are my best bootstrapping tips.
Success stories from founders who leap blindly into business without resources or relevant experience are compelling, but they’re the exception, not the rule. Working inside another organization can build your skills, your network and even inspire great product ideas.
After finishing college with a computer science degree, I worked as a developer for a New York media company. The editors always needed custom web forms, which were tedious and time consuming to build. I kept thinking, “There has to be a better way.”
That daily frustration led me to start JotForm — but I didn’t leave my job right away. I stayed with the media firm for five years and worked on my product on the side. By the time I was ready to go all in, I had the confidence, experience and savings I needed.
Many of the world’s biggest companies began as side projects, including Twitter, Craigslist, Slack, Instagram, Trello, and a little venture called Apple. If your day job doesn’t pay enough to fund the early stages of your business, consider a side gig or consulting work. There are so many ways to set yourself up for success without the pressure of VC cash or selling a chunk of your business.
The exact numbers shift every year, but data compiled by Fundable show that only 0.05% of U.S. startups are backed by VCs. Another 0.91% are funded by angel investors. The vast majority, at 57%, are funded by credit and personal loans, while 38% get funding from friends and family.
It may feel like most founders raise multimillion-dollar rounds, but that’s simply not the case. It’s also good to remember that securing VC money is complicated and time consuming. You can spend months taking meetings and presenting the perfect deck — and still leave empty handed. Be patient and stick to your own path.
SaaS founders often emphasize vanity metrics, like user acquisitions and total downloads. These numbers can measure short-term popularity, but they don’t reveal how users and customers feel about your product — or your long-term potential.
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The phrase “pull yourself up by your own bootstraps” was originally meant sarcastically.
It’s not actually physically possible to do — especially while wearing Allbirds and having just fallen off a Bird scooter in downtown San Francisco, but I should get to my point.
This week, Ken Cuccinelli, the acting Director of the United States Citizenship and Immigrant Services Office, repeatedly referred to the notion of bootstraps in announcing shifts in immigration policy, even going so far as to change the words to Emma Lazarus’s famous poem “The New Colossus:” no longer “give me your tired, your poor, your huddled masses yearning to breathe free,” but “give me your tired and your poor who can stand on their own two feet, and who will not become a public charge.”
We’ve come to expect “alternative facts” from this administration, but who could have foreseen alternative poems?
Still, the concept of ‘bootstrapping’ is far from limited to the rhetorical territory of the welfare state and social safety net. It’s also a favorite term of art in Silicon Valley tech and venture capital circles: see for example this excellent (and scary) recent piece by my editor Danny Crichton, in which young VC firms attempt to overcome a lack of the startup capital that is essential to their business model by creating, as perhaps an even more essential feature of their model, impossible working conditions for most everyone involved. Often with predictably disastrous results.
It is in this context of unrealistic expectations about people’s labor, that I want to introduce my most recent interviewee in this series of in-depth conversations about ethics and technology.
Mary L. Gray is a Fellow at Harvard University’s Berkman Klein Center for Internet and Society and a Senior Researcher at Microsoft Research. One of the world’s leading experts in the emerging field of ethics in AI, Mary is also an anthropologist who maintains a faculty position at Indiana University. With her co-author Siddharth Suri (a computer scientist), Gray coined the term “ghost work,” as in the title of their extraordinarily important 2019 book, Ghost Work: How to Stop Silicon Valley from Building a New Global Underclass.
Ghost Work is a name for a rising new category of employment that involves people scheduling, managing, shipping, billing, etc. “through some combination of an application programming interface, APIs, the internet and maybe a sprinkle of artificial intelligence,” Gray told me earlier this summer. But what really distinguishes ghost work (and makes Mary’s scholarship around it so important) is the way it is presented and sold to the end consumer as artificial intelligence and the magic of computation.
In other words, just as we have long enjoyed telling ourselves that it’s possible to hoist ourselves up in life without help from anyone else (I like to think anyone who talks seriously about “bootstrapping” should be legally required to rephrase as “raising oneself from infancy”), we now attempt to convince ourselves and others that it’s possible, at scale, to get computers and robots to do work that only humans can actually do.
Ghost Work’s purpose, as I understand it, is to elevate the value of what the computers are doing (a minority of the work) and make us forget, as much as possible, about the actual messy human beings contributing to the services we use. Well, except for the founders, and maybe the occasional COO.
Facebook now has far more employees than Harvard has students, but many of us still talk about it as if it were little more than Mark Zuckerberg, Cheryl Sandberg, and a bunch of circuit boards.
But if working people are supposed to be ghosts, then when they speak up or otherwise make themselves visible, they are “haunting” us. And maybe it can be haunting to be reminded that you didn’t “bootstrap” yourself to billions or even to hundreds of thousands of dollars of net worth.
Sure, you worked hard. Sure, your circumstances may well have stunk. Most people’s do.
But none of us rise without help, without cooperation, without goodwill, both from those who look and think like us and those who do not. Not to mention dumb luck, even if only our incredible good fortune of being born with a relatively healthy mind and body, in a position to learn and grow, here on this planet, fourteen billion years or so after the Big Bang.
I’ll now turn to the conversation I recently had with Gray, which turned out to be surprisingly more hopeful than perhaps this introduction has made it seem.
Greg Epstein: One of the most central and least understood features of ghost work is the way it revolves around people constantly making themselves available to do it.
Mary Gray: Yes, [What Siddarth Suri and I call ghost work] values having a supply of people available, literally on demand. Their contributions are collective contributions.
It’s not one person you’re hiring to take you to the airport every day, or to confirm the identity of the driver, or to clean that data set. Unless we’re valuing that availability of a person, to participate in the moment of need, it can quickly slip into ghost work conditions.
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There’s a widespread belief among founders that venture capital is a precursor to success. VC is a common denominator of the most successful tech startups, but it isn’t a prerequisite. To help illustrate this, here are 35 companies that started with a few thousand dollars, or even just sweat equity, and went on to become exemplars of what I call “efficient… Read More
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We want to see you in New York for Disrupt NY 2017, our annual celebration of all things startup. It’s a great time. You get to meet great founders and VCs and I’d love to meet you personally when I run through the alley with our video team. Hardware is my favorite thing in the world and you’re some of my favorite people. Disrupt runs from May 15-17 and will be held on Pier 36… Read More
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Who needs galleries when you can just flip through a stack of artworks on your phone, swiping right when you like what you see and left when you don’t? The yes/no sifting mechanism popularized by dating app Tinder continues to oil the wheels of many a fledgling startup — such as bootstrapping Swiss based art buying app wydr. Read More
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