T.S. Elliot, in his poem The Hollow Men, writes:
This is the way the world ends
Not with a bang but a whimper.
I recently ended my 3-year journey as a start-up founder, not with a whimper but a bang, and it was one of the best decisions I’ve made.
When a start-up, a project or an employment relationship goes south, it matters how you end things, far more than how you start them. It’s hard because instead of shouting from the top of the world about the excitement you have about what the future holds, you’re broadcasting from a hole you’ve dug yourself into. However, precisely because it is so hard, doing it well speaks volumes about who you are as a professional and as a person, and will open far more doors than it closes. It signals that you can be trusted, that you have a growth mindset, and that you are resilient in the face of adversity.
For three years, I poured every ounce of my being into my start-up. I walked away from a steady FAANG paycheck, and moved my family halfway across the world to Silicon Valley, all to take my shot at building a successful venture-backed company.
I was a founder. That was my identity.
Saying it was hard to quit is a gross understatement. But this post isn’t about how I made that decision; it’s about how I implemented the decision once it was made.
I can say now that I managed to turn what might have been perceived as a weakness into a strength. I parlayed a story about failure into a success story.
Here’s how, and here’s how you can too.
1) Confront and own your mistakes
When founders choose to communicate their decision to shut down their start-up, most write a ‘goodbye letter’ that goes out to investors and their extended support network. Some use it as an opportunity to celebrate what they accomplished. Others use it to chronicle their journey from start to finish.
My goodbye letter was a post-mortem. Here I was calling ‘time of death’ – how could I do that without also documenting ‘cause of death’?
While external market conditions were part of the story and were out of my control, there was a lot that I could and did control as a founder - including what market to focus on, how to go to market, and when and how to pivot. I carefully examined the decisions I made, and owned up to the fact that some decisions turned out to be bad ones.
2) Learn from your mistakes but also crystallize, document and share your learnings
So I made some mistakes. We all do. It’s called being human. The question isn’t whether you make mistakes or how much that cost you; the question is whether those costly mistakes will have been worthwhile.
Mistakes you don’t learn from are things to regret and can be a source of shame or embarrassment. If you learn from your mistakes and don’t repeat them, then you’ve converted something regrettable into something to be grateful for. When I reflect back, I realize that I wouldn’t have learned or internalized the lesson if I hadn’t made the mistake in the first place. As Laura Schaffer, VP of Growth at Amplitude, says: “Failure doesn't have to be a wall, it can be a compass, it can be the thing that leads you to the right thing.”
The exercise of writing up what you learned is the process by which that compass takes shape, and sharing the write-up can help lead others to the right thing. In letting others in on your lessons learned, your mistakes become even more worthwhile.
3) Do it out in the open
I’m a big believer in aligning what I think, what I say, and what I do. That means that with me, you always know where you stand.
I owned my mistakes in the open. I called every one of my investors to share the news and give them a chance to process and ask me questions. I’ll never forget how hard it was talking to one angel investor who wrote us two checks over two rounds. As it dawned on him that he was never going to see that money again, the silence was deafening.
I then sent my goodbye/post-mortem letter not only to my start-up’s investors, but also to the wider network of investors I had one day hoped would fund my start-up.
I also published it on LinkedIn for my entire network to see. Almost 14,000 people saw my mea culpa.
In doing it out in the open, I told the world I felt no shame or embarrassment about my start-up failing. I also played a small part in correcting the survivorship bias that exists in the startup world, where you think all startups succeed because you only hear about the ones that do.
Many people told me they benefited from reading my lessons learned. Others shared it with founders they knew. Others still asked to speak and go deeper into what I’d learned.
The dividends from #1 and #2 above multiplied because I did them out in the open.
4) Sit in the discomfort
This one was by far the hardest for me personally. Through working with coaches, I’d pinpointed that I can have a tendency to work harder and get busier as a way of avoiding sitting in discomfort.
There’s no tangible output of just this part of the process, but it was only by forcing myself through this personal process that I was able to do all of the above from an authentic place.
5) Enlist support throughout the process - both moral & practical support
My first few phone calls to trusted investors also doubled as calls for help: “How do I navigate this?” The best advice I got was: “Show us what you’ve learned.”
My goodbye letter went through more drafts than I can count. I shared the work-in-progress and invited direct feedback from my inner circle. Based on feedback, I threw out early versions in their entirety. Just as I couldn’t let my pride be the reason I stayed attached to a failing start-up, I couldn’t let my ego be the reason I drafted a mediocre goodbye letter.
It was the ultimate exercise in letting your guard down, and I hope everyone is lucky enough to have the kind of support network you can be this vulnerable with.
***
In the end, my goodbye letter left my reputation with investors intact, if not improved. The response I got was unexpected:
"From when we first got your deck we marked you as a team to watch, and that remains true despite where you landed - maybe even truer. Please know that your wrap up email is phenomenally impressive."
"I just wanted to say what a brilliant, honest, thought provoking close out email this was."
"For what it’s worth, this is one of the most insightful, thoughtful and gut wrenchingly honest perspectives I’ve heard of or read in years."
On LinkedIn, my goodbye letter and post ended up being the single highest engagement post I’d ever made, outdoing announcements about being featured in Forbes or being accepted into top-tier accelerators. In addition to 13K impressions, I got a ton of comments and DMs.
When I shared it with strangers I wanted to meet, they were more inclined to meet with me. When I met with strangers who’d read it, they came into the conversation already thinking more highly of me and my capabilities. (Spoiler alert: one of them went on to hire me.) The letter got sent around by friends, acquaintances and investors. I was told over and over that the fact that I wrote this and shared it spoke volumes about my character.
At first, I was a little taken aback by how positive the reaction was and how much of it I got. Then I realized why: as a society, we have come to expect people to hide when things aren’t going well or go quiet when what they have to say isn’t what people want to hear.
In ‘quitting’ my start-up how I did, I defied expectations. I beat the odds and stood in my vulnerability. I turned my vulnerability into my strength.
And you can too, starting now. I’d like to invite you to seize the moment and put my advice into practice right away. Here’s how: Leave a comment about a time you quit and did the opposite of what I advised above. And try answering these two questions: what you could have done differently and what might have been different as a result?
Maria Wang-Faulkner is a product manager and career coach. Here is her start-up post-mortem. If you would like her help to reflect on and post-mortem a past job, career, start-up or project, she has offered to do this for a handful of Elpha members - for free. To take advantage of this, send her a DM on Elpha with what you’d like to post-mortem and why.
