20 things I learned as a startup entrepreneur

As I approach my final days at Bib + Tuck, I’ve spent some time reflecting on lessons learned since the conception of this business venture more than three years ago. This post, addressed mostly as a reminder to myself, is a summary of some of the things I learned in the three years of building this company:

#1 Be wary of startup experts. Advice, by nature, is simple and straightforward, while starting a company is not. There is no roadmap or definitive guide that applies universally to all businesses. Every startup is unique to the specific problem/market it’s targeting. Other people can tell you what’s worked for them and you should listen carefully, but let your intuition guide you.

#2 Run a business, not a startup. The tech startup culture has given birth to a vibrant social scene, ripe with enough panels, meet ups, fireside chats, and conferences to keep your schedule busy every night of the week. But the fact is that unless your customers are startups themselves, most of these events are a distraction (with one important caveat I address in point #4). Your job as a founder is to put in the long hours of focused work to make your product amazing, and doing that right will consume all of your time. While other startup people are having a beer, throwing around startup buzzwords broadcasting ideas they have yet to build, you’ll be one step closer to making your product perfect. Every startup founders dream is to be featured on TechCrunch, and so was mine. But you know what TechCrunch coverage did to my business? It led to hundreds of inbound pitches from SAAS businesses and marketing consultants. And you know what coverage on Refinery29 did to us? It gave us 5,000 new paying customers. The key lesson here is: be where your customers are, not where the startup industry is.

#3 Nobody is out of reach. It is still possible to get in front of critical people without attending every “how to use content to grow your startup” panel. We live in an amazing world, where everyone is literally available with the touch of a button. Some of the best people I met throughout my experience I reached out to coldly via email or a tweet. You’d be surprised how effective that can be if you entice them to meet with you in a way that’s targeted and efficient. For example, I once saw Elliot Tomaeno from Astrsk PR was teaching a class on successful PR tactics at General Assembly that I wasn’t able to attend. Instead I sent him a tweet to treat him out to lunch in exchange for a 1:1 recap of the class. And he did. I also reached out to one of the startup founders I admire most, Sophia Amoruso of NastyGal via Linked-In and that led to developing a relationship in person. Social media may be daunting and intimidating, but it gives you access to your heroes. Take advantage.

#4 Learn to speak. There is one important caveat to point #2, and that is speaking events. I took on every opportunity to address an audience, whether it was investors, customers, students, journalists and it was the single best thing I did throughout this experience. Take EVERY opportunity you have to speak about your company. I am totally not the person I was back in 2011, and I largely credit the opportunities I’ve been given to take on speaking challenges. This doesn’t only apply to large audiences — even if you’re in front of a couple people, or friends of friends — the elevator pitch is more important than you’ll ever imagine. If you can’t explain what your startup does in one or two sentences, you probably haven’t found the right words to describe it.

#5 DIY is nice, but you need a real team. I tend to favor being scrappy and hiring slowly, but your company won’t survive long if you’ve got a great idea surrounded by a mediocre team. In the early days, you will be driving the product vision and doing a lot of the nitty gritty. But in retrospect, I micromanaged the business for far too long and wasn’t able to effectively transition from being product owner to focusing on the rest of the company. Ultimately, a CEOs job is to assemble the best team, not to execute. On that note, pick people with positive outlooks; negativity is viral and it only takes one person to turn an entire company upside down. It happened to us. The lesson here is, if you get company culture right, everything else should take care of itself. A great culture leads to happy employees, happy employees beget happy customers, and happy customers beget happy shareholders.

#6 Learn to have hard conversations. This one was particularly challenging for me and is a skill that I am very consciously working on improving. Firing people, apologizing, giving and receiving feedback, saying no, convincing investors, and delivering bad news are all situations you will face as a startup founder. It’s easy to dance around the issues and sugarcoat things, but it’s a lot harder to be direct and say things like “This isn’t working out.” “We’re not going to hit our milestones this quarter.” “We can’t give you a raise.” “I was wrong.” Delivering disappointment is not easy, but people will respect you and trust you for it.

#7 Transparency. Somewhat related to the previous point, but over communicate with your team and share results (financial and key metrics) with the company every month. Or even better, share them with the outside world. It makes you accountable. One of the best examples of this I’ve seen is the Groove company blog, where the CEO provides a rare, uncensored, and brutally honest view of the company’s wins, fails, and lessons along its journey to $500k revenue/month.

#8 Your assumption should be that nobody wants your product. My intention here is not to be cynical. This is an essential mindset that forces you to focus your time on finding who wants the thing that you’re building. Users don’t care about your product, they care about themselves, their problem, and finding a solution for that problem. As founders, we have a tendency to get emotionally attached to our idea and become dismissive of criticism. Assuming that no one wants what we’re building forces us to remain objective.

#9 Celebrate your wins as a company. When you’re burdened with a list of unmet goals, it’s easy to overlook what you have achieved. But not pausing to celebrate weakens motivation. It’s important to unify people around positive outcomes. People yearn to be inspired. Make them feel appreciated and give them a higher meaning for their work at your company.

#10 Make money. You can have a business that customers love, but if enough customers aren’t willing to pay you more than it costs to run your business, then there is no business. Don’t naively assume that the money part will take care of itself, validate your assumptions. The success of Google and Facebook is often used as an example to show that you don’t have to focus on generating revenue to create the proverbial ‘unicorn’. But they’re the exception rather than the rule. Revenue is important, it gives you the freedom to honor your values and it is the single most important metric to judge the health of your company. If your idea can only monetize at scale, then fundraising matters and someone in the team will have to actively take on this role. Discuss this with your co-founder(s) before launching.

#11 eCommerce is tough: The problem with eCommerce is that the joy of the consumer experience and top line growth is not yet met by strong business fundamentals. Zappos created the standard for ecommerce companies — free shipping, free returns, great prices, great customer service. But the irony is that all other businesses ended up emulating a company customer’s loved but which remained financially non-viable — Zappos ultimately sold to Amazon in 2009. Our buyers expected free shipping, free returns and great prices while our sellers expected maximum value for their sales and low commissions. Our sales and growth picked up substantially when we gave our customers discounts and perks, but it was shocking to realize how little the return was after subtracting acquisition costs, support costs, free shipping and other gimmicks that have become a given in e-commerce. Andy Dunn of Bonobos wrote a fantastic piece on the topic, with clear, action-oriented takeaways on what drives success in eCommerce.

#12 Execute. This one speaks for itself. There are more half written novels than published books. Break down your idea into actionable steps, set a deadline, and ship your project.

#13 Be different. Identify your unique selling point and build a story around it. There are too many apps and websites and standing out has becoming increasingly difficult. If you take a quick survey of some of the most successful companies, you’ll find they have shockingly clear mission statements. For example, Walmart’s “to help people save money so they can live better”, 7 Eleven’s “around the clock, around the corner, around the world,” Google’s “we organize the world’s information”, Ritz Carlton’s “ladies and gentlemen serving ladies and gentlemen”. These companies found a way to reduce their lofty and sometimes complex goals to one sentence so you clearly understand what makes them who they are. Some more recent examples of beautiful brand storytelling I’ve seen are mattress company Casper, Everlane, and Warby Parker. These companies make sharing their story easy. Their uniqueness can be easily articulated.

#14 Fear doesn’t go away, it simply evolves. One of our advisors, Ali Hamed, wrote one of the most thoughtful pieces on the subject here. But to sum up, the challenges you deal with will just get bigger and more complicated over time. I now see CEOs of companies who have raised tens of millions of dollars and I empathize because I know they are afraid. But fearlessness is like a muscle, the more you exercise it, the more natural it becomes to not let your fears get the best of you.

#15 Beware of chicken and egg products. For a two-sided business to work, both producers and consumers need to be on the platform. But consumers don’t see value in joining the platform when there are no producers, and vice versa. You may have the best interface in the industry, but in 2-sided marketplaces, liquidity is the most important KPI. In other words, if you provide a seller with a pool of qualified buyers, and a transaction happens, they will continue to sell through you. Otherwise, they will go elsewhere. eBay may be sketchy. But from a seller’s perspective, sellers will take flakes and weirdoes any day of the week so long as there are buyers. This is not to say that marketplace businesses are not good investments; some of the most disruptive new businesses have successfully gotten around this issue (think Airbnb, Uber, etc…). But you have to have a plan to scale quickly, because in platform businesses, to be the best, you often have to be the biggest.

#16 Don’t waste your time building it in-house, leverage APIs. Nowadays, there’s an API for pretty much anything, which means you don’t have to build your entire tech stack from scratch. For example, instead of building sophisticated site search tools, leverage a tool like Algolia. Instead of building fraud prevention tools, use a tool like Sift Science. Instead of building user reviews and social features, use a tool like Yotpo or Olapic. There’s a perception that building it in house is easier, but using third party services is always cheaper (and more sophisticated) than building it in house. The risk of course is that many of the companies offering these tools are startups and you never know when/if they will suspend their services. But do your research and leverage them.

#17 Replace the phrase “I don’t have time” with “this isn’t a priority”Not sure where I got this, but it’s one of the best pieces of life advice I’ve ever received. For example, instead of saying “I don’t have time to exercise,” try saying, “Exercising isn’t a priority.” It doesn’t feel good, but that’s the point. Doing this prevents you from ignoring the truth and allows you to better prioritize your goals. It’s amazing the impact that this small mindset shift can make in your life and work.

#18 Entrepreneurship is glorified. This is contentious, but I truly think it is a misconception to believe that being an entrepreneur is something anyone can/should do. You have to have an almost crazy level of dedication and hustle within you to succeed, which is not something everyone has. Few people talk about the hardships and the sense of isolation that comes with being an entrepreneur, probably because it doesn’t fit with the perceived personality type of the stereotypical entrepreneur. But if you don’t have high tolerance for stress, I think it’s just as respectable (and effective) to join an existing company pursuing an idea you believe in.

#19 Be humble. There are plenty of smart people who get nowhere. Don’t beat yourself up about your failures. Acknowledge that an important part of anyone’s success is luck.

#20 Lastly, know that it’s not a straight line. The media makes it sound like startups trajectories are linear. But straight lines are for bankers and 9–5 employees, not entrepreneurs. The straight line story for Bib + Tuck might seem to follow the stereotypical startup lifecycle: talk to people… build an MVP… learn… pivot… grow… sell… etc but that ignores the intricacies and highs and lows we experienced throughout the process. What journalists won’t tell you is that there’s a dirty prelude to every success story. People think it looks easy because they don’t know the whole story. As Twitter’s cofounder once said, “Timing, perseverance, and ten years of trying will eventually make you look like an overnight success.”