I led marketing strategy for Fuckup Nights NYC.

Fuckup Nights was a paid event series hosted in WeWork locations around New York City: Chelsea, Brooklyn Heights, Grand Central, and FiDi.

Each event we hosted 3 successful entrepreneurs to share their stories of failure.

Over the course of 6 months, we hosted dozens of founders to share their stories.

Founders came to our events and talked to our audience about how they failed. Our event format was like The Moth's: stories are true, as remembered by the storyteller and always told live. Speakers have complete discretion and talk about their experience of failure as they wish.

What I learned from founders about failure

Stories about business failures are persuasive case studies

So much advice we hear in life comes from people who have personal motivations and incentives that influence the advice they give. Because of that, it’s difficult to trust and follow advice others give us.

Instead of hearing people tell us what to do, when we hear people tell us about their mistakes it’s easier for us to learn from their experience and apply these lessons to our own lives because vulnerability inspires trust. We often learn more from stories of failure than from success stories.

There are many ways to fail in business and much to learn from business failures

Founders shared their experience of failure in many different ways and unlike hearing success stories, these stories never failed to be entertaining.

Founders talked about how they crashed their startups into the ground. They told us how they became financially successful while their relationships fell apart. They told us how they succeeded briefly while destroying their marriages. They shared how selling millions of drugs in the LES prepared them to create a successful life outside prison. They shared how they raised money until they lost control of their company. They shared how they burned themselves out working late night after night with no end in sight.

More important than what founders failed doing, was how they failed.

Talking about failures in detail helped founders and attendees learn from their mistakes

It's rare for founders to have an open opportunity to talk about failure. To ensure success, so much of their time must be focused on developing a positive reputation for themselves and their business. That process doesn't allow showcasing much personal vulnerability. Many founders enjoyed presenting at Fuckup Nights because they couldn't easily talk about these experiences and share them elsewhere. Many found the experience cathartic.

At our events, founders openly talked about their business challenges: working with co-founders, negotiating equity, talking to customers, selling, fundraising, finding advisors, working with board members, hiring, managing employees, growing their bottom line, keeping customers, and selling their companies.

Founders detailed when they realized they had made mistakes, what the outcomes of those mistakes were, and what they would have done differently the next time around. They told us what signals people should look out for and what false positive signals kept them from seeing issues.

Founders are responsible for identifying the most likely reasons their business would fail and addressing those risks

Taking small and repeatable risks produces results that helps you identify better paths towards success. But many types of risks result in failures that close off paths to success. Our founders spoke candidly about when they failed to differentiate between fatal and non-fatal risks and were blindsided by the negative consequences as a result.

Founders repeatedly expressed that identifying which risks need to be avoided and which risks are worth taking is fundamental to being successful in business. By hearing directly from founders about their failures, we were given privileged insights on what sorts of risks prove fatal and which founders need to prioritize addressing in their business.

Founders must avoid "fatal risks" and pursue non-fatal risks

Almost all founders we hosted talked about risks they took in business and the differences between these two types of risks. Many founders talked about the everyday risks they took to persuade others on the value of their business. These founders took risks to persuade co-founders, their first customers, and investors. These risks were mostly to their reputation.

Several founders talked about their experience taking “fatal risks”. These were risks that could kill their business or stopped them from trying the same approach again. Some founders we hosted bet their business on fatal risks and lost their businesses when they lost the bet as a result.

Failures often feel personal and are hard to notice when they happen

For many founders, their experience of failure wasn’t confined to business. Failure often felt personal and served as a reflection of who they are. The challenges our founders experienced in business strongly affected their personal lives.

Founders became invested in their business identity and in the stories they sold their customers, investors, employees, and themselves as they worked hard to make their business vision a reality. Their blood, sweat, and tears went into their businesses as did the fabric of who they are.

Founders' failures were often not obvious at the time. Founders often noticed failures later once the effects of failure became engrained into their business results. This lagging effect made founders experience of failure more painful and caused them to seek out people with previous experience more as a result.

Failure inspires humility and respect

Among the founders who spoke at our events, the true gems easily stood out.

The audience and those of us who carefully listened noticed which founders took real risks and cared about the people who might follow in their footsteps. Some entrepreneurs were all too ready to talk about themselves and hand down advice to our audience, but those who did were easily forgotten.

The founders who were remembered best were those who shared their struggles and talked about failure from experience. These founders held themselves back from giving out advice. They understood enough to know how much of their success was the result of hard work and much of it was luck. Their experiences humbled these founders enough to prevent them from patronizing the audience and the audience, in turn, respected founders for opening themselves up.

Stories about failure are hero’s journeys

It’s a beautiful thing to hear founders talk about failure. You can feel emotion come through in their voice. At every event we hosted, we heard another hero’s journey. Each Fuckup Night's story described another person who set off into the unknown and encountered challenges that resulted in struggle, transformation, and personal progress.

Unlike many stories about startups, the stories told at our events weren't idealized narratives of "how we made millions" or "how we save the world from today's biggest problems". A Fuckup Night's story is about breaking through self-doubt and taking action. This is a story that’s easy to love because it’s one we can relate to.

At Fuckup Nights, for the first time many people saw founders as they were instead of the polished images many entrepreneurs had crafted for themselves. Instead of company bios, we saw founders' real character and humanized selves.

In a community that's obsessed with hyping the next big thing, hearing about failure is refreshing.

What I learned about marketing events

Event series are dual-sided markets (at a minimum)

To ensure event series stay interesting for attendees, events need outside talent their audience is interested in.

Creating a successful event series depends on giving both your audience and the talent you host great reasons to come and to leave them with a positive experience they'll remember.

Every dual-sided market has one stakeholder type that's harder to satisfy. At Fuckup Nights, satisfying the needs of speakers (the founders we hosted) was more important than satisfying attendees because getting a great lineup of speakers had a bigger impact on our success.

Events series with external sponsors have at least 3 stakeholder types that need satisfying to be successful. We were sponsored by a few different companies (for example: Hooch). But many event series are self-sponsored. Meaning they are hosted by companies as a means of customer discovery or company branding.

Event series are labor intensive

We were lucky at Fuckup Nights to have dedicated team of volunteers who enjoyed our events and would happily trade their time helping us setup and close down for free tickets to attend our events. Completing set up and close required significant time and effort from volunteers: 1-2 man-hours of work in total for each event.

A big part of why we were able to put on events in multiple WeWork locations was that we worked with WeWork staff to ensure event setup and close worked with the needs of WeWork members and didn't disrupt normal community activities.

What I learned about marketing

The key to mastering social media is creating content for your audience's audience

Growing emotional engagement with customers is important for every business and social media is big part of how companies do this today.

Social media is one of the most effective ways to develop customer relationships and improve your brand especially for B2C businesses, so without a solid strategy to grow your social media engagement you'll be missing a huge part of your businesses potential growth.

To succeed in social media, create content for your audience's audience. Create content that influencers and your social media following either emotionally resonate with or think will make them look good, so they'll be happy to share it with their followers.

Retention is often more important than acquisition

If Fuckup Night events were so great, why didn’t Fuckup Nights grow into something big and stay around?

In the time that I ran marketing for Fuckup Nights, we grew all our acquisition metrics by more than 100%, ticket sales, revenue, email subscribers, social engagement, etc. We expanded from hosting one event per month to two a month, and finally to hosting an event every week.

But in that time period, average event attendance from event to event hadn’t risen. People were still paying the standard rate of $15 to attend every event and we had gained event sponsors, but attendance was soft.

We had expanded our events too fast to continue growing with momentum.

A quick dive into the numbers revealed the problem was worse than appeared. Attendee engagement and retention was well below healthy. The percentage of attendees that came back to a future event in the next month indicated we didn’t have product-market fit.

What did I learn?

While marketing's primary focus is usually growth, it’s often more important to improve customer retention.

Investing more time and effort into understanding our customers and what they did and didn’t want would have led to subtle conclusions that our event format didn’t fully satisfy the emotional needs or wants of attendees.

We prioritized growth without first ensuring we were satisfying the customers we already had.

How would I have done things differently?

To ensure attendees were satisfied, I would have prioritized customer discovery instead of growth. As I know well now, the best way to ensure your marketing messages will work is by ensuring you understand who you’re marketing to.

Using what we learned about our best customers would have lead us to improve our event series for the health of the underlying business and facilitate long-term growth.