These now-successful founders failed (hard) so you don't have to

There's no better way to learn than through trial and error... and it's a whole lot less painful if you learn from the trials and errors of others. 😅

I asked successful founders about their biggest fails and f ups, along with what they took away from their experiences. Let's learn from their mistakes. 👇

Building in secret

Marc Louvion of ShipFast:

It's 2017. I believe I am Mark Zuckerberg. I can't tell you my secret idea because you might steal it. I over-engineer an app in my bedroom in the daytime, and I design the perfect logo at night.

One year goes by and when I finally decide to launch, someone asks me "How are you going to make money exactly?". I'm puzzled. I haven't thought about who's going to use the app.

24 hours later, I hate my startup. I hate it so much that I throw away a year of code, break up with my girlfriend, and move to the other side of the world.

Ah, in case you're wondering, the app was Tinder for sports lovers — to easily find a sports partner around you (keep it secret please).

Learnings Ideas don't matter. The earlier you share them, the faster you know if they're worth your time.

95% of startups fail. Validate your idea fast, move on fast. Someday, luck will find you.

Over-focusing on the competition

Jay Tan of Zylvie:

Earlier in my journey building Zlappo (circa 2020), I was so obsessed with stalking my closest competitor, Hypefury. We were both indie hackers who launched around the same time, but somehow they were getting traction faster than me.

So I subscribed to their email updates, I checked their product every day to see if any new features dropped, and, if they did, I copied them immediately. I was so obsessed with keeping up with them in every way possible.

I even downloaded a list of Hypefury's followers on Twitter and personally DMed them a personalized offer to try to get them to switch. When a few of them gave me the time of the day and asked me what made my product better or different, I had the whole "guppy fish at feeding time" look — I was stunned and had no response.

And all the while I was neglecting my very own paying customers! I was like an obsessive ex following every single move of my competitor, when I should have been laser-focused on the needs of my customers. I was driven by jealousy and toxic competitiveness to try to one-up them. I legitimately prioritized feature parity with my competitor vs. solving the supposedly mundane issues of my customers. And my MRR reflected it. I stagnated for months around $500, despite constantly adding new features and trying to poach new customers.

I thought that if I were better than them, customers would have no choice but to use my product instead of theirs. But this isn't how the real world works. Customers don't have perfect information about all the players in the market. They are susceptible to marketing/FOMO/herd mentality. And they also buy from people they know, like, and trust.

Learnings: It taught me that, in business, the battle isn't fought outside; it's fought inside. If you're growing, it's because your house is in order. If you're declining, it's because you're imploding from within. No competitor can decide your fate.

Keeping up or imitating competitors is a fool's errand. Should you be generally aware of what your competitors' moves are? Sure, it's important to keep abreast of what the "state of the art" of the market is like. Should that be your #1 priority that drives your product roadmap? Hell no.

What should drive your product roadmap is your own users' needs -- nothing else! Just because you're in the same exact market niche doesn't mean your own users have the same exact needs as their users.

Do your business (and your mental health) a favor. Focus on your own customers, your own product, your own journey.

Not talking to customers

Guillaume Moubeche of Lempire:

In the early days of lemlist, soon after our launch on AppSumo, I decided to start billing people on a monthly basis to start growing our MRR. However, I quickly realized that our conversion rate was not as high as expected. We had new signups but very few sales.

To understand this, we implemented behavioral tracking metrics and looked at the numbers. I made the hypothesis that our activation rate was low because our platform was too complicated to use. And based on that assumption, I rebuilt the entire platform, then pushed the new version… without warning our users. 😅

I was convinced that it was the right thing to do, but when I think about it now, I realize how stupid it might sound.

Our users clearly showed their dissatisfaction with the new UX. As a first-time SaaS founder, I really felt bad because our users were usually super friendly. Luckily, my technical team decided to put their robot mode on and fixed all of the different glitches that people were complaining about.

Within 24 hours, we fixed the issues and entirely changed the perception of the new platform.

Learnings: After a few weeks of iterating on that new version, we realized that we actually improved our conversion rate from free trial to paid customer by 3x. We also increased our activation rate by 4x and reduced the time it took to create a campaign by half!

In the end, communicating with your users prior to a huge UX update is key. But, I realized that trusting your gut, even when it’s tough, can really make a difference!

Not validating ideas

Joshua Tiernan of No Code Founders:

My biggest mistake was not validating ideas properly. I naively convinced myself that the ideas were going to work regardless of what the data was telling me. I repeated this mistake with multiple startup attempts over a full decade before I finally worked out what I was doing wrong.

Learnings: Ironically, having so many failed startup attempts has given me a pretty good sense of which ideas have a chance and which don't, so I now find it much easier to pick a business that will get traction right away... but I still test every time.

That normally means jumping on calls with some people in the industry to talk to them and learn about their challenges so that I can identify whether the business will work or not.

Kevon Cheung of BIP Mastery:

I used to build inside my head.

What I mean is that I used to imagine what people needed, look up existing solutions to justify my hypothesis, and then build a 10% better product. The result? It was insanely difficult to acquire & retain users.

Learnings: After picking up the Build in Public framework (and later teaching it), I don't build inside my head anymore. I am laser-focused on serving one group of people and I ask a ton of questions to get signals and feedback in public. When I make up my mind to build something new, I keep looping in my audience to make sure I'm on the right path.

This is such a different approach. I feel like I no longer need to do whiteboarding or brainstorming; I just need to get good at talking and listening to the community. They literally have all the answers I need if I know how to talk to them.

So now I'm building everything outside my head. You should too!

Not optimizing for long-term contracts

Steven Goh of Proxycurl:

My biggest mistake was letting brand-name customers become too significant in terms of usage and share of revenue, and not converting them into long-term Enterprise contracts.

When they churned — and they did churn — the sudden loss of significant revenue was not a nice pill to swallow.

Learnings: I learned the importance of a customer success team — I mean, I finally get it after so many years of wondering why companies have that. We are now signing regular customers into long-term contracts, which is reducing churn.

That said, this is a problem that comes about with scale-ups. In the early days, most startups should only be worried about building a great product and having amazing inbound marketing.

Skipping analytics

Alexander Isora of Unicorn Platform:

My biggest fiasco was neglecting product analytics. I knew it was a must-have thing. And it sounded so easy: Just plug in a JS script and enjoy the stats. But in reality, the task turned out to be so troublesome that I procrastinated on it for 4 years!

I couldn't figure out which tool to use. And setting it up was problematic too. So I just ignored product analytics. Such a mistake!

Learnings: Setting up Posthog and finally learning what my users were doing was the turning point in my life as a SaaS creator. I learned about the most used templates. I learned what was causing churn and how to win churned users back. I learned that users from specific countries weren't paying, and created a special plan for them. And so on.

Product analytics is a ticket from the mysterious world of assumptions to the objective world of numbers. If your SaaS is >1 year old and you have over 100 users, set up analytics!

P.S. Posthog is pricey, but they have a "startup" program which will give you enough credits for the first 12 months.

Over-committing (and pissing off your co-founder)

Alex Hillman of Stacking the Bricks:

One of the biggest mistakes I've made was over-committing myself. It cost me tens of thousands of dollars.

In the very early days of 30x500, Amy and I rewrote most of the course every time we ran it because we were learning so much about what people actually needed on the fly. In many cases, that meant we were re-writing large portions of the course week-by-week. All of this was transparent with our students, but it was also a lot of pressure on us.

At one point, we had sold 150+ seats to the semester-long version of 30x500, and a few weeks into the course, I realized I was in trouble. I was still balancing client work with my own business and this new project with Amy, and had bit off more than I could chew. I wasn't pulling my weight as a partner, and it showed. Amy was pissed at me.

So I said “Look, if you think it makes sense, I’ll give my portion of the money back from this last version of the course.”

Learnings: Bottom line for me is that when I'm working with someone, I value the friendship more than the money. But also, I value the potential to ever work together again, and sometimes that means making really hard decisions in the short term. Like giving back what was a lot of money for me at the time.

That experience established what me and Amy’s professional relationship was going to be like. We need to be able to be honest with one another when things aren’t going the way we want them to, or when one or the other is not holding up their end of the bargain.

Unexpected tech meltdowns

Pichou of Naker:

One day, at my former company Homadata, we released a big update to our backend. At first, everything went pretty well. But very quickly, we ran into our first problem: We couldn't make a request to a specific route. We looked into the problem but couldn't find an explanation, so we decided to try a new Apache configuration... aaaaaaaaand boom! Everything went down.

There was panic, and everyone in the company sensed that something serious was going on. We had already passed the end of the working day, but everyone decided to stay and try to find a solution by any means necessary. Even the non-technical department stayed to show their support. We ordered pizzas for everyone and searched all night for a solution.

We found out that our Apache modification triggered a security flag with our domain provider, and that we had to contact them to deactivate it. As it was late, we knew we'd never get an instant answer, but we sent a few emails and tickets to their support in order to get the fastest possible response, and everyone went home. The next morning, everything was back to normal.

Learnings: It was tough and we were all exhausted that day, but I still had a great time with my colleagues. One of the best, quite simply because we showed each other that we were a strong team and that, no matter who was struggling, we'd be there for them.

Years later, we still remember it, laugh about it and even refer to it to new arrivals as "panic day". The day reminded us of who we were as a team. It was an important event in the development of our corporate culture.

Being careless

Brad Adkins of Designfly:

The biggest failure I recall happened when I was producing my music full-time at bradkinsbeats.com. For Black Friday, I put together a bundle of 200 beats for $99. I then launched an advertisement for this offer on beatstars.com.

After the first day of running the ad, I knew something was off. While I’m used to this type of offer doing very well, I only managed to get one sale. I logged in to investigate, and that’s when my heart dropped. My beat store was empty! All 200 beats from the bundle had disappeared.

While setting up the bundle, I mistakenly set the price at $99 for Exclusive Rights instead of the Unlimited Lease. When a beat is sold with exclusive rights on BeatStars, the platform deletes it to prevent a second sale.

I had to cancel the order and refund it, then re-upload all 200 beats again, along with their metadata. By the time I finished, it was too late to schedule another ad, missing out on thousands of dollars in revenue given my previous success with a similar Black Friday ad the year prior.

That’s not even the worst part. When the beats were deleted, all backlinks to those beats were also removed, and they were no longer part of any playlists they had been saved to. As a result, my website's traffic plummeted overnight, and I’ll never know the full repercussions of this simple but dire mistake.

Learnings: As someone who tends to work fast, I've learned when to slow down and double, triple, and quadruple-check my work. Years of hard work and SEO efforts can be wiped out in an instant.

Outsourcing before doing it internally

Luca Micheli of Customerly:

I wanted to create a sales team but had no experience in outbound sales. So, I decided to outsource it to one of the most successful agencies on paper. They had a track record with a similar solution in a different market, so I thought I'd found a shortcut to success. However, after six months and 36,000 euros with zero results, I realized I'd missed the mark.

Learnings: Before you ever consider outsourcing a core part of your business, like sales, you must first understand your own positioning, marketing messages, and communication processes. By doing this internally first, you're better positioned to manage an external team effectively. This lesson has since been integral in how we approach not just sales, but other key aspects of our business.

Ignoring platform risk

Angus Cheng of Bank Statement Converter:

In early 2015 I was working as a game developer. In my free time I developed a virtual girlfriend chat app called Girlfriend Plus. It was selling really well, so I quit my game programming job. And a month after I quit, my app was removed from Google Play. Revenue went from $5000 a month to $0 immediately.

The issue was I had paid models to use their Instagram images in Girlfriend Plus. Unfortunately, I used some photos which had been taken by a photographer, and he owned the copyright. This photographer reported the application for copyright violation and it was removed from Google.

To deal with this, I formed a new company and relaunched the app with a different name. It was annoying because it set growth back by about 18 months.

Learnings: I learned a bit about the nuances of copyright! More importantly, I realized that developing for controlled app stores like Google Play is not a good idea. They can kill your business overnight.

This event and others have led me to strongly prefer building web applications.

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