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Ask IH: Share your failure stories (and what you learned)

I'd love to hear any IH failure stories. Courtland does a great job covering the successes, but it's healthy to have a balanced perspective. I'll kick it off!

Years ago a friend and I built a CRM for local political campaigns. In a years time, we built up a $10k MRR customer base. Unfortunately we took too long building a v2. Without new features, customers grew frustrated and we lost momentum. As revenues dwindled, we decided to shut it down. Lesson learned: release early, often, and in small feature blocks :)

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    Launched a Gmail-based to-do list app back in 2011. It made $2300 MRR in the first month we charged for it. Rather than sticking with it and growing the revenue, we pivoted away and built some generic undifferentiated productivity tool that ultimately flopped. Biggest lessons learned:

    1. Customers paying you is a sign of product-market fit, even if you don't think your product is particularly impressive.
    2. Validate something before you spend 6 months building it.
    3. Avoid huge rewrites. Instead make incremental improvements, so you can learn as you go.
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      Could we have a series on failed projects and failure in general? :)

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        I don't know if I'll build something like this into the website as a first-class citizen, but maybe! Until then, I think threads like this are a great way to share.

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          Maybe a section under interviews would be cool.

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      Thanks for sharing and great advice. I definitely learned #3 the hard way :)

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    My biggest mistakes over the years tended to be caused by not focusing and getting distracted by shiny objects. There's a huge amount of value that gets created by doing more of whats working every single day, even if it's boring. Startup founders tend to be creative tinkerers. When something gets monotonmous, they move on. When a marketing channel, product or anything else starts to get a semblance of traction, that's the precise time to double down on it.

    Looking back, I wish I had stuck with blogging and various other projects where I was doing well, but ultimately got bored and moved on. With my current startup, Tettra.co, I've learned to embrace the grind and enjoy the process. In the past year, we 4x MRR to $25K and plan to do it again this year. And I finally realize the only way to do that is by doing a little bit towards the goal every single day.

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      Appreciate the advice, Andy. I'm definitely with you on the compounding returns. Will be excited to see you hit $100k - keep us posted!

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    Check out failory.com

    Their website is dedicated to interviews about failed startups, and I think they source a lot of their interviews from past failed businesses of IH interviews.

    I did an interview for them of my previous failed businesses - https://failory.com/interview/delite

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      Looks like it's ripped off from IH, UI looks so similar...

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        It definitely could be. Who cares though, the content is what matters.

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      Great idea! I'll have to check these interviews out.

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    I got 2 stories to share:

    1. In 2008 I already had a side gig going with 2 partners, but was frustrated with our pace and some decision-making (I wanted to market product more aggressively but got nay-ed on the budget). So I started my own project - build a fantasy game for MLS (that's Major League Soccer) simply because I thought I could do better than Yahoo Sports (which I did). I built the whole thing from scratch and by myself and functionally it WAS better than any other app on the market - at the time I was the primary developer for MLS official site MLSnet.com and working out of MLB.com office so I knew the stats and space very well.
      The issues:
    • The biggest problem as you can guess was that the demand for it was so low that I couldn't monetize the product well, even at $5 CPM for the premium audience. I was running a dedicated server to allow myself full control and mgmt of DB and raked up CC bill.
    • It was high-maintenance because I was scraping official stats that could be corrected 1-3 days after a game and if I ran score updates too early and there was a correction I was in updates hell.
    • I was doing everything myself and I burnt out after 1 season/year.
      Lessons learned:
    • Size up the market to make sure it's not a micro-niche
    1. I started a business with 2 partners - another developer (my best friend at a time) and a product SME (his relative). We all got 33% share of biz but put no formal agreements in place on our roles and responsibilities or any accrual of equity over timeline - we had 1/3 ownership from day 1. Needless to say that effort spent wasn't even at any given time and eventually tensions kicked in over that. I ended up buying out the business form original 2 founders after lost momentum and 6 years and pivoted/grew it into a successful business that got acquired (interview is gonna get posted in a couple days).
      Lessons learned:
    • always have a founder agreement in place to define roles & responsibilities and have a vesting schedule in place (that's what all VCs actually look to have in place)
    • don't loose momentum - very hard to get back on track
    • grow fast to get to exciting milestones (esp. financial goals) - life events get in the way and team looses momentum and excitement
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      don't loose momentum - very hard to get back on track

      So important! We didn't appreciate this until we lost our momentum.

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      I ended up buying out the business form original 2 founders after lost momentum and 6 years and pivoted/grew it into a successful business that got acquired (interview is gonna get posted in a couple days).

      Wow, great recovery! I think most people would've quit at this point.

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        The business was making low 5-figures at this point, not enough if you split 3 ways, but some potential for 6-figure income for someone willing to invest more into it.

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    Got two stories to share.

    1. I stumbled upon a small gold mine back when Android was just taking off. (I was a student at the time, so even small $$ were relevant). I published a fun app with close to zero competition, was getting good downloads and due to a unintended UI bug the CTR on the ads was like 5-10x of what was a usual click rate on similar apps from my friends. So after a few weeks I got a good ammount of "Beer and fun money" monthly... So far so good.

    Unfortunately I was too dumb to see the opportunity and the relevance of the timing ( Android as a distribution platform was just beginning to grow exponentially)

    I should have done two things in hindsight:

    • double down on the app concept and release more similar apps to grab market share
    • double down on the Android market in general and use all the free time (plenty) for other projects instead of using it to spend the few bucks I made with the one app on beer ;-)

    Lesson: Be smart enough to know that you are just getting lucky. And double down immediately!

    1. I had an idea for a web app but no time to do it myself so I thought "Lets just outsource this thing". It was my first experience with oDesk and Outsourcing Dev work. No clear specification, no budget, etc.

    As you can guess ... I spent around 1000 € in the first week until I panicked and realized the contractor was building something without specification but was using so much hours for even tiny Features that it would take around 30k for my tiny tiny web idea. Keep in mind that the 1000€ was like two months worth of living for me back then.

    Lesson: Think it trough before you start on something new. I still fall into that trap with new projects once in a while. But at least I dont spent money before I have a plan how to get it back ;-)

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    Biggest lesson I learned with my first project is: clients don't care about your code. I was trying to build things nice from engineering standpoint. Ended up with tons of wasted efforts. Can talk about that for hours.

    Launched backtrac.io in a year. Could have done it in few months instead if didn't write any automated tests, saved on the design etc.

    Second lesson. Focus on money. Project should be bring money from day 1 (dream scenario). Realistically -- set the deadline and budget. Second project we made it to be "break even" after half a year. After a year project made a return of investments.

    Third lesson. Be lean, cheap and build dirty MVP solutions. Longer you can stay in the game -- higher chances you have for success. You will have time to refactor and build thing properly once you have actual business.

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    10k seems like sizable revenue to just toss in the towel. What was the last straw that made you decide to shut it down?

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      Yeah, it really was unfortunate. 10k was peak MRR. By the time we finally shut it down months later, most of our customers had jumped ship and we were down to $2k MRR.

      Ultimately, we shut it down because we were burnt out. In different circumstances, I think we could have pushed through and recovered.

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        You probably should have sold it before you burnt out. Anything would have been better than shutting down. Many would have loved $2k/month (can work from a beach somewhere).

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          I know! I wish I knew about flippa back then :) And unfortunately the $2k wasn't purely passive due to the support involved - so it became a distraction as we moved on to new projects.

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    Launched a case management app for elected representatives, had a fairly successful beta and pushed to live. Almost overnight, everyone stopped using it, but we chugged along with 3 individual users and one major customer (with 25 users).

    A little while later, that customer left us and we had zero engagement, no new sign-ups, it was all going to the dogs. Explored the whole process in a blog series (https://medium.com/@stevenjmesser/please-give-me-another-chance-f1a1555c8974), but I learned
    – to build around user need,
    – to understand your positioning in the market, and
    – how to turn things around even though it goes against everything your boss believes.

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    Alder was the second iOS app that I built. It gives you one relevant political action to take each day directly from your phone. My goal for building this app was to get more people involved with politics and social justice.

    Alder was my first project where I followed Paul Graham’s famous advice to, “do things that don’t scale.” Since Alder provides users with a political action to take each day, I have to write a political action every day. I load them into my Firebase database each day. I’ve gotten into a good routine, but this has still been challenging. There have certainly been a few days that I’ve woken up early on a Saturday and realized I forgot to load the day’s daily action and all users are receiving error messages.

    My failure in this project was not building something that was sustainable and not being able to grow the user base to make it worth my time and energy to work on.

    My biggest learning was the need to balance not focusing too much on scalability for an MVP, with the realities of upkeeping an app that isn’t automated. While it’s good to “do things that don’t scale,” I need to find the right balance. Building things that require daily upkeep from me is not sustainable long term. When I start an app I should have a tentative idea of how I can scale the workload and make it manageable if I decide to continue to invest in a project.

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    Had a great idea, hired engineers with image processing and analysis skills for my R&D.

    Problem, i had no technical background and no co-founder or CTO.

    Result : a product that didn't work.

    Also i didn't listen to recommandations , i should have focussed on an MVP, not tiny details.

    So what i've leaned is that you shouldn't start any business without the proper team.

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    Would love to learn more about your specific story

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      Thanks! I'll do a proper write up one day - will let you know when I do.