POSTMORTEMS ★ 1,084 upvotes 2014

My startup failed, and this is what it feels like

CORE FOUNDER LESSON / TAKEAWAY

“A deeply vulnerable account of the psychological toll, identity crisis, and emotional wreckage when your venture-backed startup folds.”

Retrospective Overview & Key Insights

Distilled analysis of the business dynamics, operational challenges, and strategic takeaways:

In this postmortem from 2014, @wbharding candidly breaks down the dissolution of their startup, examining the fatal assumptions, misallocated resources, and market dynamics that led to its shutdown. At its core: A deeply vulnerable account of the psychological toll, identity crisis, and emotional wreckage when your venture-backed startup folds.

Core Principles for Independent Builders:
1
Early signals were often rationalized away instead of prompting an immediate pivot in distribution or pricing.
2
The psychological toll of running out of capital compounds operational friction in a solo or small team setup.
3
Key Antidote: Validate paying willingness before committing months to building sophisticated product features.
Community Debate Themes:

Community discussions on HN centered on identifying product-market fit early, avoiding vanity metrics, and the emotional recovery process after shutting down.

Community Discussions & Critical Reviews

High-signal perspectives, counter-arguments, and peer founder insights debated on Hacker News (252 total discussions):

DO @dools Peer Contributor

This is a "fail story" that stuck with me -- wish I'd been able to suggest it when you were looking for stories similar to your own!

http://blog.jazzychad.net/2011/05/02/startups-are-hard.html

Also here are some Mixergy.com interviews that I've enjoyed from failed entrepreneurs:

http://mixergy.com/interviews/adyin-mirzaee-fluidware-interview/

http://mixergy.com/interviews/chris-snook-no-limit-publishing-interview/

http://mixergy.com/interviews/rene-eric-forecast-interview/

http://mixergy.com/interviews/dean-soukeras-computergiants-interview/

http://mixergy.com/interviews/mark-bowness-tribewanted-interview/

http://mixergy.com/interviews/james-altucher-failseries-interview/

http://mixergy.com/interviews/eric-ingram-redtagcrazy-interview/

http://mixergy.com/interviews/sebastian-replanski-search-to-phone-interview/

This is with Chad who's posted I started with:

http://mixergy.com/interviews/etzel-notifo-interview/

And, finally, if I were leaving New York, I'd listen to this:

https://www.youtube.com/watch?v=0t4i7frhNUs

Hope you're feeling better and looking forward to seeing you sometime 'round Fishburners :)

ID @iD3 Peer Contributor

22 is so young.

At 21 I was on a plane headed home from another country. I cried in the office. I cried on the plane home. We'd Burned almost half a million dollars, a couple of years of work, let go a team - and had nothing to show for it. With no degree, no more money and no job I moved back in with parents.

So I suppose this article resonates, and in the most literal sense - I've been there.

I think the hardest thing for me at that moment in time was I didn't really have a handle on just how young I was and how much more I had coming. It was all I'd really done with my life up to that point.

It's taken me quite a few years to gain that perspective, and it's a difficult thing to communicate. The world is inconceivably vast and expansive and you have the next half century to build within it. Yourself, your ideas, your creations.

At that age and on that scale it's only a failure in the moment. Then, as time passes it becomes just another step along the way. It imparted knowledge upon you, and opened doors you don't even know about yet. All of the parts that hurt fade away and you're just left with the experience gained.

The fast-paced echo-chamber of the technology startup world is a particularly hard environment to step back and get a real sense of perspective in, which makes it a particularly hard environment to fail in, especially as you'll always be reading about someone else magically killing it.

I've failed since then, and I've succeeded since then. But as the years roll by, I've come to realise that the winning and losing don't even matter, because the journey just keeps on going regardless. If I saw myself now, when I was on that plane at 21, I'd have thought I was looking at someone who had mythically 'made it'. But you know what? I haven't. It's exactly the same: I've got another 40-odd-years of succeeding and failing ahead of me, in both my personal life and my professional life.

Personally I find that quite cathartic.

RW @rwhitman Peer Contributor

I've worked with a weirdly large number of female-run and female-focused startups and clients over the years. I could write a long, blunt tirade about this.

Basically the cards are stacked against these businesses from the day they are funded.

Male tech folks make a lot of false assumptions about female focused businesses. For investors it can mean leaving a complicated business model under-funded. For developers it means blindly taking a “cofounder” title in exchange for an equity-heavy compensation deal without thinking through what it means to work on a business you aren’t passionate about, for years, at reduced pay.

In both cases, if there isn't an early slam-dunk hockey stick marker of success, guys don’t have the stamina to tolerate a female-focused business for very long. They bail. The company never gets its next round of funding. The engineering talent runs for the hills. Its not cool to work on a company for girls, especially a struggling company for girls. So male talent will just split as soon as the going gets rough.

Each time the company has a setback, the guys all start to bail. So the company needs to find new talent and appease many people at every little bump in the road. This is hugely costly and results in a lot of unnecessary crisis moments, doubts, and subsequent pivots.

The sad part is that a lot of female founders leave startups for good after one failure. I have a linkedin network filled with former female founder superstars who work in humdrum non-tech management roles. Women take the loss on a much more personal level than men do. So every time a female founder is stunted, and then abandoned by her male support network, she may be gone for good.

What’s the solution? I’m not sure, but I think it has a lot to do with adding more female investors and developers to the world. That and encouraging more former female founders to come back, mentor and try again

JP @jpatte Peer Contributor

"Fail fast, fail early, fail often!” they all chant, trying to put a positive spin on the most excruciating pain any founder could experience."

Is it just an impression, or did she get this sentence the wrong way?

The whole point of this saying is to make you realize that failure should actually not be such a big deal. Failure isn't an dead end, it's a step forward on the difficult path of entrepreneurship. Therefore, saying things like "I couldn’t fail. This was my baby, and if it was going to fail it would be over my dead body." can only lead you, indeed, to excruciating pain in case of failure.

Resilience is an excellent quality, and I think the only way to give your best and surpass yourself is by facing real challenges, but please remember that you cannot in any way resume 4 years of ultra rich/challenging experience with the two words "I failed". Jeez, just having survived 4 years in her very first startup experience is already a success.

I sympathize with her pain; I just find it sad that she doesn't seem to realize the incredible experience and skills she gained from this adventure. Those years were absolutely not wasted; the chances of success for her next startup are incomparably higher than for her previous one, and I wish her all the best for the future.

Edit: A startup is first a human adventure. After it "failed", ask yourself the right questions: - Did I learn something? Do I know better? - Am I a different person? A better person? - Did I help some people in any way? - Did my social skills improve? Did my network grow? - What about my legal/technical/managerial/whatever-ial knowledge?

If you can answer "yes" to any of these questions, than this adventure wasn't a failure at all. :)

GU @GuiA Peer Contributor

I met Nikki while I lived at a Hacker House in Mountain View for a few weeks in January 2012, having recently moved to the Bay Area. I remember being impressed at the time by her intensity, and by the fact that she actually had a real product with real users that solved a real problem.

An audible "oh no" came out of my lips when I clicked this link and realized I was reading about someone I had shared a few dinners with.

It's important for little pieces of history such as this one to be recorded. For the founders, to whom it gives a sense of closure, and for the community. So that we don't forget our comrades who didn't make it to the other side, but still have insightful lessons to share.

The press likes to glorify the AirBnBs, the Googles, the Facebooks - but as founders, I think it's important for us to be realize that this is only a tiny visible part of the iceberg, and that at the end of the day, there are so many factors at play that it would be foolish for us to focus solely on the "how many millions did they make". Human stories are never boring, and experience is one of the most precious thing others can share.

Thanks for taking the time and effort to write this, Nikki. We're with you.

---

"Investing money, creating new products, and all the other things we do are wonderful games and can be a lot of fun, but it's important to remember that it's all just a game. What's most important is that we are good too each other, and ourselves."(http://paulbuchheit.blogspot.com/2012/03/eight-years-today.html)

HISTORICAL ERA Cloud & Mobile Era (2014–2019)
COMMUNITY SCORE ★ 1,084 points
TOTAL DISCUSSIONS 252 comments
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