When Your Start-Up Fails

We are inundated with stories of successful start-ups and their founders. But sometimes — and in fact, most times — a start-up just fails. There are stories here too, stories that are worth telling. Here’s mine.

Marrio31/ Getty Images
Marrio31/ Getty Images

We are inundated with stories of successful start-ups and their founders. In this narrative, failure is shown primarily as a prelude to success, setting the stage for redemption — the founder overcomes massive odds story. But sometimes — and in fact, most times — a start-up just fails. Barring a spectacular fall from grace, coverage of these failed start-ups is often reduced to a few sad paragraphs in TechCrunch. But there are stories here too, stories that are worth telling. Here’s mine.

Three years ago I co-founded a business, Revere, with my longtime boss and mentor, Matt, and a third cofounder, Alex, who we were introduced to by an investor. On the surface, our start-up had all of the ingredients for success — huge market, seasoned operators and $3.5M in venture capital from name brand investors. We didn’t succeed though, and now, months after we wound down, I’m still trying to come to terms with what went wrong. My postmortem largely boils down to one question:

Whose company were we really building?

I’d spent my entire career working at early stage start-ups and had developed an itch — no, a dream — to build something myself. Matt and I had long talked about starting our own thing, regularly pitching ideas back and forth, and in 2016 he was approached by a group of well-known investors. They weren’t looking for his ideas; rather, they were on the hunt for an operating team to launch a business that was already being incubated: Warby for sports nutrition, or, said another way, We’re going to burn GNC to the ground. They chose Matt to be their guy, and he asked me to join. I was pretty sober and honest with myself (and him) about it. No, I wasn’t passionate about sports nutrition, and this didn’t exactly feel like mine — but I believed in the opportunity, and I thought the mission was a good one: building a better supplement company, one with transparency and integrity at its core (Hell, I’d be a customer). Most importantly, here was my chance to start a company — how could I pass it up? I joined (as COO), and we quickly brought on Alex (as CMO). She was the perfect complement — unlike Matt and me, she had extensive experience in the health & wellness space. I could already see the three of us on the cover of Fast Company.

The Revere founding team (from left: Matt, Alex, me). I was 28 when we started Revere. Three years later I have significantly more grey hair.

There were competing visions from day one, and in hindsight, it’s clear that we never fully reconciled them. One of the investors had come to the table with an existing asset: a renowned human performance expert, Mike, who’d already developed a line of safe sports nutrition products (technically speaking, this was the actual corporation that we’d be “starting”). Their vision was to build out this existing line and create the go-to supplement company for professional and elite athletes. This was more than just a “competing vision,” though — there was concrete pressure for us to go in this direction despite the fact that Matt, Alex and I were less than enthused about it. Alex thought we should become the GNC for the studio fitness consumer (or the “SoulCycler,” if you will). And I wanted to create a product line for people like me — the longtime GNC goer who’s grown tired of sketchy products and is looking for healthier options (“I’m ready to replace that giant tub of pre-workout on top of my fridge”). And then there was Matt, whose unenviable job was to reign in all of the visions and forge a viable path forward.

I often wonder if things would have gone differently had we fully committed to just one of those visions, each of which has real upside. But we didn’t — instead, we put each of the visions into a melting pot and trusted that what came out would be a winner. We hired a top tier agency to help us develop our brand voice and aesthetic, and all three of us attended the strategy sessions. In fact, all three of us made most decisions together in the early days. Here’s where I think we landed:

We rebuilt the products to cater to the reformed supplement user (from my vision), as opposed to the elite athlete (which Mike’s original line catered to). Our origin story, though, still spoke to our heritage in elite athletics (Mike’s vision). And our brand and marketing targeted the studio fitness consumer (from Alex’s vision). Now, there’s certainly some logic to this. The products struck a nice balance between efficacy and health (all-natural but built for performance). All athletes are aspirational, so putting Mike and his experience in elite athletics at the center of the story made sense (à la Nike and MJ). And there’s just a hugeamount of white space in the studio fitness market — the new breed of fitness consumer has rarely if ever dabbled in sports supplements before, a gap we looked to fill.

Marathon flavor-testing session.

It’s not to say that we thought we could be everything to everyone. It’s more that we didn’t have a singular vision, a north star, that kept our organization moving in lockstep. We were a bit too fast and loose in the partnerships we forged, events we hosted. The press that we drove across different types of media outlets (tech versus lifestyle versus health & wellness) didn’t stick to a clear, consistent message. Our buying model (personalized subscriptions) wasn’t totally compatible with our consumers’ buying habits. And we tried to compensate for all of this by pouring money into paid marketing channels.

TechCrunch headline on launch day.

So what did that net us? A mediocre launch, mediocre growth, a lot of money spent, and major identity issues. Five months into our launch, our investors were (rightly) unsatisfied with our progress and direction. Now, most start-ups don’t get it right out of the gate — the search for product-market fit is known to be an iterative, experimental pursuit and most great businesses are defined in that murky period of trial and error. But that wasn’t in the cards for us; as we worked to right the ship, a faction of the board began second-guessing many of our decisions, particularly those that went against their preexisting vision for the business. They demanded wholesale changes — a demand that quickly transformed into a huge amount of pressure applied directly to Matt and Alex. The way the board was structured, this one faction was able to overrule our other investors and board members, many of whom supported empowering the founding team to work through the changes ourselves. Less than six months after our launch — without the support of the board and facing impossible headwinds — both Matt and Alex left, and I was handed the keys to Revere.

Why was I the one effectively left in charge of Revere? Perhaps the board saw something special in me that made me the right choice — that’s certainly what my mother would like to think. More than anything else, though, it was a simple process of elimination. Alex had been running marketing, the easiest thing to blame when sales aren’t going well. Matt was the boss, so he was going to take the brunt of it regardless. And somebody had to be kept around to keep the machine running — as COO, that was essentially my job. But in reality, I felt every bit as much to blame for our struggles as Matt or Alex, and I had strong feelings of survivor’s guilt. We’d been through this roller coaster together, and suddenly, they were both gone. I could write another essay entirely on this, but I’m going to spare you the details here. I’ll just say that as painful and difficult as that time was, if there was an ounce of resentment from Matt or Alex, it was never shown. I’ve got nothing but love and gratitude for both of them (and we’re still friends).

Okay, so we’re 1.5 years into starting the business, six months into launch, and I’ve been asked to take over. Simply put, my job was to sharpen the vision, pivot and rebuild the business, and find that rocketship growth that VCs are so fond of. It felt like an impossible task, and I nearly quit. I asked myself, how did we get here? Competing visions, overcompensating for lackluster sales with paid marketing, and an unhealthy dynamic between CEO and board. If I could address these issues, maybe this thing had a shot. I talked it over with my friends and family and decided to go for it. Finally, something that never felt like mine could become mine.

I put together a thirty-slide deck that showcased my vision, and how it would extend across every facet of the business. We’d hone in on the frustrated (or lapsed) sports nutrition consumer who’s tired of choosing between the sketchy, powerful products from GNC and the healthy, crunchy stuff from Whole Foods. Our new product statement would be Elite Sports Nutrition, Powered by Nature, and our brand would feel both premium and gritty. Our line would gradually expand beyond sports nutrition, into healthier versions of a wide array of functional products. I made it clear to the board: take it or leave it — there could only be one vision, so I’d only take this on if there was 100% buy-in. To my surprise, I received it, with the caveat that they’d be looking for a seasoned executive to partner with me. I was totally on board with this (I’d take all the help I could get), but it never came to fruition.

At this point it was just myself and Arielle, our Director of Ops. We spent eight months rebuilding everything — our products (added flavors, changed packaging form), brand (from trendy and cute to edgy but refined), website (pivoted from a subscription model to more traditional e-commerce), marketing strategy (shifted from paid to earned growth), and team (grew to 6 FTEs). We relaunched, and that first month was the best month we ever had, with zero dollars in marketing support.

Revere 2.0 website, packaging and branding.

Finally, things were looking up. The team was excited, motivated. We were getting great feedback from customers, new and old, about everything from the new flavors to the new brand and packaging. It seemed that we’d achieved product-market fit. Most importantly, numbers were trending in the right direction.

Keith and Miles hosting a sampling event.

Except for one — money in the bank. We’d burned through nearly all of our seed round, most of which had been spent prior to the pivot. We were not in Series A territory, so we’d need to raise a seed extension round. One of my investors, Andrew, rallied behind me and the company’s turnaround by stepping up to create a term-sheet and commit a meaningful investment from his own fund. We quickly received commitments from other existing investors, but the group was already overleveraged, so we’d need to bring on some outside funding as well. The inside funds brought us to $1.3 million, and it was agreed that we’d need to bring on at least $2 million to have a real shot.

Completely new to fundraising, I went into the process confident and enthusiastic. It quickly became a full-time job on top of my other full-time job of running the company. The tone was set right away; I spoke to nearly 100 investors and heard some version of the same thing every time: “Very impressive turnaround, but given the history and financial situation, this investment is too risky for us.” After weeks and weeks of this, feeling completely drained, I found myself manufacturing enthusiasm in every pitch meeting.

With three months of runway left I stopped taking a salary. Sales continued to steadily climb, but we had no money to spend on marketing and we weren’t close to being profitable — plus we still had a significant amount of outstanding debt from both our original launch and the relaunch. Doing my best to broadcast optimism, there was a stark contrast between the energized vibe in the office, and how the fundraising process was going, not to mention what I was feeling inside.

Fundraising continued, and I kept hearing “thanks but no thanks.” With two months of runway left, an existing investor who had previously committed $500K to the round pulled out. I vividly remember the visceral feeling of hearing this news; truly, it felt like a kick in the stomach. Suddenly, things became dire. I had a come-to-Jesus meeting with the board — outside funding might not be feasible at this stage, and now we were down to $800K committed, 40% of our goal. Another option was presented: recapitalizing the business and raising money at a significantly lower valuation, something that would essentially mean starting the fundraising process over and wiping the original stakeholders off the table (Matt and Alex included). We decided to think about it for a few days and then regroup. I got drinks with one of my investors, Ben, who’d been nothing but helpful and supportive from day one. He said something to this effect:

“You’ve been pushing a boulder up a mountain for a year now. If this business fails tomorrow, that does not mean that you’re a failure. You should be proud of what you’ve done here, and you’ve got a long career ahead of you.”

He wasn’t telling me that it was over, but he was telling me that it could be over.

For months I’d been telling myself that I couldn’t let Revere fail, it wasn’t an option, there was too much riding on this. My conversation with Ben shook something loose in me, and I went home and broke down. I was so f*cking exhausted, physically, mentally and emotionally. I’d barely been sleeping. My mood had been completely unstable — I was living and dying with every investor meeting, every uptick and downturn in sales. I was neglecting friends and family, and my relationship was failing. And I was lonely. Feeling the need to keep a strong front, I had walled myself off, hiding my inner turmoil from my employees and investors, and avoiding talking about it with people outside of the business who I was sure just couldn’t understand. I’d been telling myself that this was all normal, this was part of the entrepreneurial journey, but suddenly it all caught up to me. I tried to dig deep and find something to help me keep fighting, but I came up empty — any passion once there had now been sapped. I wasn’t sure I could push the boulder any further up the mountain.

I was preparing to tell the board that I thought we’d reached the end of the road, but they’d all independently come to that same conclusion. The whole group was remarkably cordial and supportive about it. The board orchestrated a quick sale of the business (…not the kind that’s covered in TechCrunch), and I’d stay involved for another month or so to help manage the transition. I had to lay off my entire team, one of the worst days of my life. Again, this day could be the subject of another essay, but I’ll just say that the sense of shock and disappointment in the room was palpable, and delivering the news felt like an out-of-body experience. I’ll never forget these words from our Director of Marketing (who’d joined at the beginning of the pivot):

“It’s like we’ve been training for a marathon for eight months only to get kneecapped at the starting line.”

I went home and drank whiskey by myself in a dark room.

You spend every waking minute trying to realize your dream, and then one day it just hits you — it’s not happening, at least not now. My peers have insisted to me that there’s no shame in it. I’m reminded that Steve Jobs, Walt Disney, Oprah Winfrey, and so many others failed countless times before seeing real success. Sure, intellectually I know this, but for some reason it doesn’t lessen the sting. I do feel shame in having let so many people down — my employees, investors, and of course, myself.

There was no “getting right back on the horse.” I’ve had to stay down for a while, try to heal. About two months after this all went down my brother and his wife had a healthy baby girl, Zoey, and I became an uncle. With plenty of free time on my hands, I’ve learned how to change a dirty diaper, and have even earned the privilege of babysitting from time to time. I did some traveling and began reading and writing again — two longtime hobbies that I’d all but abandoned. I spent two days knocking on doors in a NJ swing district to help flip the House, and I became more involved in helping my Little Brother, Chris, deal with the challenges of his sophomore year of high school. Perhaps most importantly, I unsubscribed from How I Built This and a number of other start-up-related podcasts, and began listening to music on the subway again. Sometime during these past few months I’ve been able to separate my full identity from my “founder identity,” a feat that can be reallyhard for us entrepreneurial types to accomplish.

A very milky Zoey and me.

Of course I still think about Revere constantly. For one, I’m proud of what we built. Our products delivered on our promises — they were both healthy and effective — and thousands of people loved them. I still have a stash, one that’s often plundered by my friends, that I dip into nearly every day. And our eight-month turnaround is the most impressive professional feat I’ve ever been a part of. I’m also incredibly grateful to have met so many amazing people, including a number of investors that did all they could to set us up for success every step of the way (and I should add that despite the turmoil, there was never a question of anyone acting in bad faith). But I’ll always be disappointed about how things ended. My chest still tightens up every time I’m asked about Revere (near-daily, it seems), and I don’t think the second guessing of my decisions and abilities will ever fully go away. From a practical sense, the big question that still lingers in my mind is:

Would we have succeeded if we’d had a unified vision from day one, across the board and entire team, that informed every last decision that we made?

From a more personal, introspective sense, I wonder:

Would I have kept fighting at the end if I’d felt more passionate about and more ownership of the idea/business itself?

Both can be boiled down to: whose company were we really building? The answer to each, unfortunately, is I don’t know. But here’s what I do know — next time I start a business, I won’t have to ask myself these questions. To get through the hard times — a pit of self-doubt and loneliness — you need complete and utter belief in what you’re building, and a board that’s fully behind you and your vision. Any other way and there’s just no point.

It’s now clear to me that it’s not success for the sake of success that I’m looking for, but I’d be lying if I said I didn’t still dream of that Fast Company cover. Maybe it’ll come true one day, and maybe it won’t — but either way, I’ll continually remind myself that there is more to me, and more to life, than making my own “start-up success story.”

For more of my work, please follow me on Twitter and check out my website.

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