The successful startup is fast becoming the new American dream. The plucky founder—with a garage, a few bucks, and head full of dreams—sets about to create something that the world didn’t even know it needed in the first place. But all of a sudden we all can’t live without it. Cue the fame, fortune, and magazine covers.
However, the reality usually isn’t quite so fairytale. In fact, as we’ve discovered, founding a startup requires pain, uncertainty, and lots and lots (and lots) of failed ideas. We spoke with several of the well-known founders who have been in the tech trenches themselves (from companies like HotelTonight, BeenVerified, GreenPal, and more), who have emerged victorious afterwards and know exactly what it takes to succeed. So read on, and for more great career advice, check out The 25 Ways the Smartest Men Get Ahead at Work.
Launching a successful startup is less about the “a-ha” moment and more about what comes after—the trial-and-error slog of execution. “Your initial instincts, no matter how strong, are often wrong,” says Jeff Gothelf, a speaker and coauthor of Sense & Respond: How Successful Organizations Listen to Customers and Create New Products who led the UX design teams at TheLadders and Web Trends. “While the problem they’re solving may be real, the solutions you first envision for these problems are usually wrong.”
Those who’ve suffered through the process of starting a company know to trust more than their instincts—and to not take it personally when they make a bad call. After all, taking things personally is just one of many things a man should let go of by his 40s.
There is never a need to reinvent the wheel. “Someone has tried the thing you’re doing and has likely written about it or shared their experience somewhere,” says Gothelf. “The startup community is filled with the generous experience and insight of previous founders.”
Startup founders know that being first is far less valuable than being willing to learn from those who have come before. This means seeking out books, blogs, podcasts, interviews, YouTube videos, and even Facetime with others who have followed a path you would like to go down in order to “understand what worked and didn’t for them before making the same mistakes they did,” as Gothelf puts it. For more great advice, read up on the experiences of famous leaders and businessmen such as Mark Cuban.
Once you get on that entrepreneurial highway, it’s tough to find an off-ramp. “There’s no real point at which you stop hustling,” says Samar Birwadker, CEO and founder of workplace and networking platform Good&Co. He describes how originally he had the idea that once “success” was reached, things calmed down, and the founder handed off responsibilities and kicked back while everyone else worked. That didn’t happen. Even after building up Good&Co. and shepherding it through a successful acquisition by private market specialist StepStone, Birwadker isn’t walking away.
“My company means so much to me that I pour as much energy into now, with over 50 employees, as I did in its nascent stages at TechStars.” That may mean logging time on weekends, so make sure you know how to do it right.
Working hard doesn’t mean micromanaging. Birwadker says you need to loosen one’s grip as the company scales. “Founders have trouble delegating and relinquishing control even at a point where it makes no sense for them to have a hand in everything—that’s just the nature of going from a one-, two-, or three-person company to having 50+ employees,” he says. “The transition is difficult, but good founders will emphasize making smart hiring decisions in order to be able to trust the management abilities of those below them.”
Those who don’t learn this lesson generally see their company fail. As personal as the organization might be to you, its success depends on it leaving your hands and others contributing to its expansion and elevation. Bonus: delegating to your employees shows confidence in them, which is one way to make sure you’re not a bad boss.
Successful startup founders have found that the most profitable results come from workers who have some level of autonomy. “Give parameters, not permission,” says Sam Shank, founder and CEO of HotelTonight, the platform for last-minute hotel deals at top-rated properties. “You’ll be amazed by each person’s ability to respond to the challenge, blow past targets and dig into resourceful solutions.”
He points to HotelTonight’s head of user acquisition, Brian Han, who launched a new partnership that “turbocharged our bookings.” “He understood and was on track with our profitability plan, so asking me for permission would’ve wasted time and slowed down the process,” says Shank. “Give your team the freedom and space to innovate — and execute.” Take some inspiration from Google, one of the most innovative companies out there.
As a startup founder, you want to build a great product, an effective team, and keep your costs down. But you soon learn that you’re also building something else: a culture. And the decisions you make will impact every aspect of your organization and will shape its success.
As he’s guided HotelTonight into a major force, the thing Shank is perhaps most proud of is the company’s culture. “I got to build the kind of company I wanted to work at, from the ground up,” he says, pointing to its open-floor plan with long tables where everyone sits, the bar in the office, and perks like catered meals, HotelTonight credits and unlimited vacation. “[We take] a lot of care in the hiring process which means we’re always hiring amazing people, and which results in them being friends inside and outside of work.” To make sure you’re building the best office culture possible, check out these game-changing leadership strategies.
“There is a fine balance between friends with your team and being the CEO and founder,” says Ishveen Anand, CEO and Founder of athletic sponsorship platform OpenSponsorship. “For the first time, many founders are employing people their own age who they would ordinarily be friends with, but there is a balance to maintain.” Remember: the co-founders of Facebook were friends who famously fell out with each other, one of many interesting facts about the social network.
“The toughest business lesson I learned was: don’t spend years developing a product that doesn’t have a distinct customer base,” says Ross Cohen, cofounder of background check platform BeenVerified.com. “I wish someone had given us that advice earlier, but maybe it’s one of those things you have to learn yourself. You have to feel the pain before you appreciate it.”
He describes how it was difficult for the company to pinpoint its market. They eventually realized that targeting consumers (rather than the over-served B2B market) would be the ideal approach. These are the kinds of questions that founders must answer, through market research or other methods. And for more leadership inspiration check out these life-changing lessons from super-successful men.
Just as a singer performs better when they sing directly to an individual in the audience, a business leader does better when he has a specific customer in his mind. Appreciating the importance of having a clear image of the type of person or companies who are buying what you have to offer is another lesson that startup founders learn—not just in a demographic or geographical sense (though that’s good too), but in a personal sense. Entrepreneurs who start their own companies usually have seen firsthand the demand for what they’re offering and think of their customers not as a faceless group, but as specific individuals eager to buy what they have to sell.
“As a co-founder of a startup there, is no single job that is ever above or beneath you,” says Cohen. “For a long time, my job on a day-to-day basis was really just whatever resources we were lacking on that day. I’ve done everything from designing our website in Photoshop to coding our conversion funnels in html/css. Some days I was the sales force and others I was the customer support team.” It may help motivate you to do this by noting that some of the richest men in the world got that way founding their own startups.
Starting your own company can also alienate some people in your life—a lesson startup founders have seen personally. At the end of the day, creating a startup is a huge commitment. “Immediate family and close friends will always be supportive—sharing on social media, writing reviews, actually using your product, bringing food to the office at midnight. But second-tier friends, like your bar buddies, just don’t understand the work it takes to build something from scratch,” says Gene Caballero, cofounder of GreenPal, the “Uber of lawn care.” “They can’t fathom why you are not able to grab a happy hour or grab dinner on a Tuesday because you have to work. Slowly but surely, these friends will eventually quit asking and become mere acquaintances.”
Over the span of four years, Caballero admits that many of the friendships he had before founding GreenPal turned out this way. As with any major change in a person’s life, creating a startup is likely to impact one’s social life. And since work may take over your life, it would help to know how to conquer stress at work.
“Passion is everything when creating and running a startup,” says Steve Carlton, founder of Invitd, an invitation-via-text-message service. Carlton stresses that running a startup can be “as much exhilarating as it is exhausting” and every founder hits a point in getting their project off the ground where they consider giving up or members of their team have trouble maintaining interest in the project. Often the only thing that pushes a project over these humps is the excitement of the person at the head. He has to be the motivator for everyone, including himself, and if the passion’s not there, it’s hard to pull that off.
“If your startup has you so intrigued that you stop caring about sleep and socializing then you are on to something,” says Carlton. “Anything less means you are more likely to give up instead of fighting harder when you are backed into a corner.” Staying passionate is also one of the rules that successful entrepreneurs follow.
But don’t let you passion go too far. Remember: Startup success is like dating: Bring the energy, passion, and optimism, but don’t talk about commitment until you’ve really gotten to know each other. “Never fall in love with what you thought was the best idea. It may be and often is simply not the best idea,” says Barry Henthorn, founder of ReelTime.com, an online video-on-demand provider. “Never care where or from whom an idea comes from. Evaluate on the merits not the origin.”
Most startup founders have at least a couple, if not dozens, of failed startups behind them. The difference between those who fail quickly and move on to the next project and those who throw up their hands is that the successful guys know there is always another great idea around the corner.
“Founders learn that there are an infinite number of paths to startup success,” says Ariel Quinones, cofounder of Ironhack, a coding bootcamp with campuses in Miami, Barcelona, Madrid, and Paris. “You don’t necessarily have to be a programmer, or an MBA, or a charismatic public speaker to build a successful startup. The one constant is passion.”
Jordan French, Fast 50 serial entrepreneur and tech journalist, says that in the tech world more than any other sector, old biases and traditions are of little interest when an idea is a winner. “The beauty of entrepreneurship is that it doesn’t matter what you look like or where you’re from,” says French. “Markets are refreshingly disinterested—and purely interested in whether, how and when your product or service works.”
Carlton says that sometimes “good” is plenty good enough. There are so many things a founder is juggling and so many decisions he’s making in a given day, or hour, that to try to do everything exactly right is not just unrealistic, it’s dangerous to the success of the project. There are always tweaks and improvements to make on a platform, but by delaying the rollout of it until it’s flawless, it’s probably never going to see the light of day. “If you are launching a new product or even a new feature get it out the door as soon as possible and then let your customers guide you from there,” says Carlton. “You’ll waste less time and your customers will be happier in the end.”
Ironhack’s Quinones believes that being “the little guy” or the underdog is a huge plus. “The benefit of being a young, smaller company is that you can be extremely focused,” he says. “A large corporation can have hundreds of product lines and customer segments in different markets. Meanwhile, a startup can be successful by focusing on the needs of one type of customer.”
Quinones says that means that one’s brand, positioning, can all speak directly to a targeted audience’s particular needs. “To successfully compete with larger players, startups must capture small and highly focused market segments that the big guys are ignoring or aren’t aware of,” he adds.
Entrepreneurs have a go-it-alone spirit, but to make their startup rise into the upper echelons requires a great team—and the wrong team can lead to disaster. This is a lesson Lori Cheek, founder and CEO of app-based dating platform Cheekd, learned as she transitioned from a career as a trained architect to building her own business.
“Team is everything. I just wish someone had told me the importance of having the right team surrounding me,” says Cheek, describing an early mistake in teaming up with two people with the same skill set, who owned 20 percent equity in the company, and created big problems. “The technical aspect of my business has been one of the bigger challenges I’ve faced and it’s the one thing I definitely would have approached differently from day one. I needed a CTO. Four years later and a little shuffling around equity, I found the missing link from all those years before who’s helped facilitate and finance the new face and technology behind the new Cheekd.”
“A great idea on it’s own, is almost worthless,” says Neil Mclaren, owner and founder of Vaping.com. “Just because you build it, doesn’t mean that they will come. In fact, if you build it and it’s good, someone else will probably build something similar, and maybe better.”
Remember: many successful startups are built more on successful marketing strategies than they are on perfect products. If you still have leadership questions, see if you can get America’s Fittest CEO, Strauss Zelnick to answer them in his column for Best Life.
The most difficult part about succeeding in getting a startup off the ground and succeeding is controlling your own mindset. “Managing yourself—your time, your mood, your mindset, your emotions, your consistency, your energy, your health, your balance,” is the sometimes the most important concern for a founder, according to Ben Brooks, founder & CEO of the tech startup PILOT.
According to Ironhack’s Quinones, even though founders often have vast reserves of confidence in their ideas and the power of their ideas, how they respond to hitting an obstacle will determine whether things succeed or fail. “After a while, you need to evaluate whether your initial beliefs have been validated or you’re just swimming against the current with no progress,” says Quinones. “Navigating this delicate balance between being optimistic and grounded is especially challenging for founders.”
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