Motivation, Startups

The Challenges We Rarely Talk About When Building Startups

Credit - Reuters/Sivaram V

Credit – Reuters/Sivaram V

This curated column is authored by Ryan Hoover, Founder, Product Hunt

Nearly everyone who’s joined a startup has gone through some really hard challenges, but we often don’t talk about them. Sometimes we can’t. Here are some anecdotes from some vets that have been through it all, written by the Product Hunt team.

Everyone who’s attempted to build a startup knows it isn’t exactly a walk in the park. It’s often embellished in mainstream media (ping pong tables, and free lunches, and sweatpants to work!)—but the realities of startup life are far from glamorous. In the past several years, it’s felt almost “trendy” to start a company. Unfortunately, many startups fail and founders flounder, partially as a result of the inevitable clash between expectations and reality.

Still, at Product Hunt, we’re always rooting for people to launch products and startups they really believe in. One of the best things you can do if you’re thinking about or have just started building something new is to learn from those who have already been through the journey you’re about to go on. Below, you’ll find wisdom from 12 entrepreneurs on overcoming early challenges, prioritizing growth efforts, trusting their intuitions, and more. Read on for some great insight that will help you along your own entrepreneurial journey.

Kayvon Beykpour, Co-Founder & CEO of Periscope

One of the toughest challenges for a startup CEO is prioritizing which features to build next. What guides you in establishing the roadmap and choosing where the team should focus its energy? — Chris Sacca

It’s a mix of different inputs:

  1. Our gut. There are features we just care deeply about experimenting with, either because they feel right or directionally they bring us closer to where we think the product should go.
  2. Feedback from Periscopers! We’re fortunate in that people who use our product are comfortable sharing (on Twitter, over email, and on Periscope) what they think is missing and what could be improved.
  3. Scaling needs. This one is interesting because it’s the least predictable. We’ve had to focus on so many “features” (many of these back-end or infrastructure, and some UX/user-facing) quite simply due to how insanely fast we’ve been growing. Focusing on this category of development is both necessary (to make sure the experience doesn’t cripple as the ecosystem grows) and naturally more disruptive because it was harder to plan for.

So the interesting/fun/challenging aspect is balancing inputs 1, 2, and 3 in such a way that it feels like the product is growing, becoming more interesting, and adapting to the growing ecosystem.

Amanda Kahlow, CEO & Founder at 6Sense

What have been some of your biggest challenges getting 6sense off the ground, and how did you overcome them? — Emily Hodgins

Staying focused on our mission. I am a big big believer in not focusing on the competition. Of course [it’s important to] know your competition, but don’t try to emulate it. You know what is best for your business. Stay true to yourself and your vision. Don’t let any one person’s opinion move you; listen, but be confident. Another big challenge: The more successful you are, the more you need to succeed. We’ve had great success and the bar just gets higher and higher, harder and harder. But truly, it’s so wicked fun when you know you are doing something very different and are solving real problems.


Peter Shankman, Founder of HARO & best-selling author

When you started HARO, if you knew then what you know now, what would you do differently? — Erik Torenberg

I’d be MUCH more careful with who I hired. I hired people because I thought they could do what I could — That was a mistake. I should have been hiring people who could do specifically what I couldn’t do.

Mariam Naficy, CEO of & board member of Yelp

What have been some of the biggest challenges of founding Minted? — Emily Hodgins

I think that one of the biggest challenges to founding Minted was the availability of capital. I founded the company in 2007, when there wasn’t much interest in funding e-commerce companies. Then we hit the recession in 2008. We had to bootstrap for a very long time, and every month for years we were worried about the cash running out. We overcame it with a very strong focus on hacking/optimizing to grow revenue, [as well as] very strong financial planning capabilities. This has become one of the company’s core strengths . So in retrospect, I’m glad that our culture was shaped in the middle of a recession rather than in a bull market.


David Heinemeier Hansson, Creator of Ruby on Rails, Founder & CTO at Basecamp

What is an alternative narrative of “building something you love” and working on it indefinitely vs. the current Silicon Valley definition of success, like being acquired or hitting an IPO in ~3 years? — Jonny Miller

I don’t think growing in a sustainable, long-term way is compatible with the VC founding-to-funding pipeline. So that’s simply mission number one: Give more people the strength, motivation, and insight to reject the angel -> VC -> IPO/sale pipeline. Because once you’ve stepped on board, there’s no getting off.

So that means highlighting all of the alternatives. Like starting a business on the side, [and/or] bootstrapping it with your own meager funds for starters, then relying on real customers to take it further. It’s a boring, slow way to build a business, but for most, I think it’s far more realistic, rewarding (emotionally and economically), and plausible.

Sam Rosen, CEO & Founder, MakeSpace

How did you overcome some of your big challenges while building MakeSpace? — Emily Hodgins

There’s no overwhelming challenge to getting a business like this up and running. Maybe that happens in highly regulated industries like insurance (e.g. Oscar Health) or medical fields with FDA approval. With companies like MakeSpace, it’s the small challenges we’ve faced:

  1. Build our own routing algorithm or find a company that can do it for us (we built it ourselves).
  2. Convince our insurance company to also cover our drivers/warehouse folks. It’s easy to get coverage for people who sit in an office. But [for drivers/warehouse folks], the premium is 2–3x what it is for office workers. After two years, we finally got them to cover the entire company for personal health care (as of 1/1/16). Now, thankfully, all MakeSpace [employees] have access to these benefits.
  3. We were growing so fast, Mercedes Benz wouldn’t lease us more vehicles. Rahul [MakeSpace’s co-founder and COO] and I personally have $400K of leased van rentals on our heads!
  4. Personal stuff. The hardest part about a business is running it while still being a human being. My partner Rahul has kids and a family. It’s not easy being a good dad or a good husband when you’re slogging through a startup. I’m not saying it can’t be done. But I certainly had it “easier” than Rahul in that regard, being single and without kids. What about personal health, friendships, wanting to travel, etc? You have to be willing to put “life” on hold. But at the same time, I’ve really found that my best friends are also CEOs of other companies because they can really relate. So it’s a constant battle. I love this post to describe all the stuff you have to be willing to put up with: Entrepreneurshit.

Aaron Levie, CEO and Co-founder of Box

What type of struggles and roadblocks did you face building Box in the very beginning? — Cuan-Chai Megghross

Initially, our biggest challenge was that we didn’t know what we wanted to be when we “grew up.” We started as a consumer product that also worked for businesses, and eventually (about 1.5 years into the business) we determined that balancing these two very different worlds and use-cases wasn’t going to lead to world domination. So we went back and forth a ton in the early days, but ultimately decided to “listen” to the market and go after a space where we felt we could best innovate (and compete). That was the enterprise market.

Nathan Barry, Founder and Designer at ConvertKit

How scary was it to make the next move from working on your own content products to working on ConvertKit full time? — Jimmy Jacobson

It was actually pretty scary, since I was investing all of my available cash. But my wife was very supportive. She said, “What’s the worst thing that could happen? ConvertKit fails, we lose all our money, and have to sell the house we just remodeled. We’ll move in with my parents and everything will be fine.” She was okay with that.

I simply responded, “What? No, it would never come to that. Worst case: I’d get a consulting gig.” Having her be willing to lose everything financially in order to allow me to build the company was very empowering.

Joel Gascoigne, Co-Founder & CEO of Buffer

Year after year, you guys have always delivered top notch content and when everyone thought you had reached the limit of your transparency strategy, you managed to take it one step further. How do you keep challenging yourselves? — Ines Silva

I think the key is to remember that you can change everything. As we grow, it can be harder to remember that, but it’s always true. Earlier this year, we fully embraced experimenting with self-management, and then it didn’t quite work out as we expected. We were completely transparent about it, and it was hard to come back and say, “we’re moving away from some of those ideas”, but I think that’s the key to continuing to grow. It reminds me of this quote from Jeff Bezos, which is kind of ironic since you asked me about consistency:

“People who are right a lot of the time, are people who often change their mind. Consistency of thought is not a particularly positive trait.”

Dave Gilboa, Co-founder & Co-CEO of Warby Parker

What has been the hardest aspect of growing Warby Parker, and why do you think it is that you have managed to beat traditional incumbents at their own game? — Harry Stebbings

I think hiring and building a world class organization is always the most challenging (but also most rewarding) part of growing a business. We are now over 700 people, and growing quickly. Having our core values codified and using them as the basis of our interviews has allowed us to scale while building a cohesive and impactful organization.

I think we are able to exist and grow while operating in an industry with massive incumbents due to innovators dilemma. It is really challenging for large, profitable companies to change and cannibalize business models that drive their profitability. As a result, there hasn’t been much innovation in the eyewear industry and [we’ve had] an opportunity to change that.

Bea Arthur, Founder and CEO of In Your Corner

What would you do differently if you were to go through the whole startup experience again? — Lester Choi

I would definitely have fired people faster. Don’t ever be understanding to unreliable people. When you’re a small team, one person can ruin even the best efforts. Also, I learned the hard way about being a non-technical founder. If you have an idea and you are a hustler but your company depends on tech, for the love of your business, take a class on Lynda. Do a One Month course.

There are so many shitty developers out there taking advantage of people who don’t have technical skills or the knowledge to call them out on their bullshit. This happened to me over and over again, and finally, I became my own product person. I do deployment schedules. I wireframe. I map out acceptance criteria. I would have saved so much time and money if I weren’t so dependent on dev shops and shitty developers. And these motherfuckers are divas, too. They’re like, “I want equity. I want more money.” In no other profession could you demand that without proving yourself first, and they know that. Learn the basics before you boss them around!

Dharmesh Shah, Founder & CTO at HubSpot

How many times in your entrepreneurial career have you thought, “This isn’t going to work,” but it did in the end? — Andrew Parker

I’ve been working in startups for most of my professional career, and I’ve been on that roller coaster many times. Often, I’ve felt the “can’t be stopped” and “we’re going to die” emotion on the very same day — for rational reasons.

The one thing I’ll say: Remember that you are not alone. Everybody (including the ones you’d label as “successful”) goes through this. The frequency of the oscillation goes down over time (I experience this less with HubSpot than I did with my first startup).

This is a curated post. The statements, opinions and data contained in these publications are solely those of the individual authors and contributors and not of iamwire or its editor(s). This article was originally published by the author here. 

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