I asked over a dozen successful founders about the single obstacles they'd found most difficult to surmount on their business journeys.

Check out their answers below, and keep in mind these are all bootstrappers, so you won't find anything about raising money from investors here.

Waiting too long to spread the word

👤 Jay Caetano of AnarchoCoffee ($760/mo)

The biggest challenge for AnarchoCoffee has been spreading the message about the product. Other smaller obstacles include things like shipping and handling and just not having enough time or capital to grow the business. But I have to keep reminding myself that the company is only six months old as I am writing this. My only regret is not starting on the entrepreneurial path sooner.

Finding the right pricing model

👤 Sarah Hum of Canny ($50,000/mo)

Pricing is one of those things that never stops being a problem. You should constantly adjust as you learn and improve your product. A simple pricing change could have such a huge impact on your business. But it’s tough. On one hand, we have customers willing to pay hundreds of dollars. On the other hand, we have competitors coming in to undercut us at $10/mo. Product founders are notorious for charging too little.

Sales

👤 Martijn Wijtmans of Tripetto ($5,500/mo)

We’re still now learning how to most effectively sell Tripetto and to whom. That’s hard enough in itself and also takes time. In hindsight we should have found a way to work out the sales angle far more concretely and much earlier. In that regard self-funding has helped creativity and quality but also taken away a healthy dose of urgency.

Public relations

👤 Dmitry Dragilev of JustReachOut.io ($30,000/mo)

The biggest challenge has been learning about PR from a non-PR perspective. I approach PR differently than the leading agencies do because I am looking to scale my own business or the business of my customers differently than a massive multinational conglomerate would. The stories and products that spring from small companies need to be nimble and adjust their strategy quickly.

Insecurity about the product's quality

👤 Eelco Jellema of Sjabloon ($1,000/mo)

Early on I felt somewhat insecure about the product, and thus felt the need to list that more was “coming soon.” These promises made it a little bit stressful at times; when asked about certain features, I needed to explain how there was no set timeframe just yet. On the other hand, these “pre-announcements” gave me a better idea for the roadmap of Sjabloon, as some specific features were asked about more often than others.

Loneliness

👤 Mitch Colleran of Join It ($40,000/mo)

When building a business as a bootstrapped founder, there is a focus on the lack of capital, but one of the challenges that caught me off guard was how alone it feels. Without investors, there are fewer people to check-in with and hold us accountable. Without investors, you’re going to be slower to build the team, so it's just you for a much longer period of time.

Taking on a team-sized work burden as a solo founder

👤 Andrew Fedoniouk of Sciter Engine ($9,000/mo)

I am building, selling, and supporting an alternative to WebKit and V8 engines, which is no small task for one person. From the start, I was aware that I was taking on a huge project that other companies have devoted entire teams to, but I chose to look at it as more of a mental challenge than a technical one. I knew I had the skillset to pull it off, I just had to keep myself motivated and on track.

How long it takes to build a good product

👤 Hiram Nunez of Tee Tweets ($1,200/mo)

The number one thing I was blindsided by was the sheer amount of time it would take to actually build and run a business. You're probably thinking, "It's just a t-shirt company, how hard could it be?" I thought the same thing. Turns out: very. This is due to a number of reasons: supply chain logistics, product quality, content creation, manufacturing, and marketing.

Being a non-technical founder

👤 Taylor Jacobson of Focusmate ($700/mo)

Being a non-technical founder. This issue is such a meme but it's a serious problem. What should you do if you don't know how to code your own product? In the end, I built my first prototype myself using Wordpress, Zapier, Google Sheets, and ScheduleOnce. There are a ton of tools out there now to build prototypes without code. You can get started validating your product without learning to code, and this will help you attract resources and talent.

Delivering products to customers on time

👤 Dom Wells of Human Proof Designs ($90,000/mo)

We struggled a lot with operations when things really started to take off. We just didn't have enough people to meet the demand, and we ended up having to refund customers. Our reputation took a hit back then because those same people who now praise us in Facebook groups would go there to complain about how slow we were.

Serving customers in different timezones

👤 Gilles Bernhard of SCPlanner ($3,500/mo)

Timezones were a huge struggle at first, since all we do is based on planning events. It took a while to properly master this aspect of SCPlanner. We now have all the dates in UTC and the browser sets the timezone for the users.

Software marketing

👤 Ivan Mir of Qbserve ($2,000/mo)

The biggest challenge was a very naive understanding of how the modern internet economy works. The idea that good software is easy to promote is just as silly as the "good software sells itself" myth. I would definitely spend more time learning marketing. I still have a lot to learn, even after all the experience with Qbserve.

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