Lessons from the end.

Five lessons I learned while deciding to shut down Poppy.

There is an incredibly steep learning curve at the beginning of most ventures. I know that was true for Poppy. Every day, something new to understand, something new to learn, well enough that it kept my company alive.

There is exhilaration in these early days. A momentum that carries you along in its freneticism. It’s hard not to get addicted to it. Harder yet to learn to settle into the discipline and drumbeat of the “middle years”, where the work is just as ambitious and against the odds, but the pace needs to even out.

Here’s something I’ve learned though: the learning curve is just as steep if opposite in direction, at the end.

There is urgency and there is haste. There is never enough information and all too much input.

You find yourself getting pulled along by the momentum of your decision, begging for more time, more insight but seeing that it’s a futile request. It’s a bed of your own making and now you have to do as well as you can by it.

And yet, through it all, only one question haunts you:

Am I doing the right thing?

Here are the five ways I thought about the decision, to create clarity not only for myself but the reasoning for everyone that would be looking to me for answers that I wondered if I would ever have.

Let tenacity, not ego, guide you.

Startups are exercises in perseverance. All the odds are against your founding, your persisting, your succeeding. So when things aren’t going the way you need them to, you’re used to that — you’re used to going through walls. This is just one more wall, right? Well… maybe. You can get so caught up in going through all the walls that fool yourself into thinking you’re Superman. And when you finally hit a wall you can’t get through, the instinct is to use more force or more creativity. But there will be some walls that need to be seen as what they are: reasons to change course.

It’s why if you run your venture like a series of experiments, you can try to discern what is fundamental and what is superficial friction. Fundamental is structural issues having to do with unit economics or taxes or size of market. If they are things that don’t get better with scale, then no amount of tenacity or creativity (or money, btw) is going to help.

Don’t let your ego of feeling like Superman blind you to the fact that some walls can’t be bust through with the model you have.

Call a pivot for what it is.

Which brings us to the next most likely scenarios for a lot of start-ups: the pivot. A fancy way of saying, keep one foot in what you’re doing right now and spin the other foot into something completely different. Take a B2C play and make it B2B by selling it to employers or build out a piece of the software that was tangential to your users but you believe might have more growth potential. Whatever it is, it isn’t what you set out to build, it isn’t what your investors or employees signed up to build, but…. in the long arc of start-ups, it is life, and it is many times, the way to eventual success.

But call it for what it is. Because likely it will mean drastically cutting the team and talking to investors and essentially starting again. It will likely mean shuttering or vastly diminishing your existing service for users. There is much to recommend to it — it keeps you alive without going through the heartbreaking months-long process of winding down. But the odds are even longer. And the road is just as steep with a lot of added baggage. Fred Wilson wrote a timely post that more eloquently went into this topic. Pivots are likely the most common path for many floundering startups. It might yet be the right path. Just don’t get caught up in the hero narrative — choose it because you believe you can succeed, not because you can’t bear to have it all end.

Answer with brutal honesty — what do you want to do?

All this points to probably the most important question: What do YOU want to do? It sounds both deceptively simple and impossibly hard to answer. Does it matter what I want? I have all of these employees and investors and users. Yes. It does. Because consciously or subconsciously you’ll manage the team to that desire. So best to uncover it, examine it by the light of day and make decisions by it, as honestly as possible.

There are no right answers here — it could be that you want to bring it back down to a small team and you have enough money in the bank to make a pivot go. It could be that you’re connected to a company that you would love to partner with and they’re willing and able to talk about acquisition. And in so doing, you can continue your mission, but in a slightly different way and with more resources. Or it could be that you need and you want a fresh start. That either a pivot is not likely, or the funds are not there, or an acquisition won’t happen (or such that it’s attractive enough to do). Or you need a break, a breather, a new perspective.

Doesn’t matter where you land. It will be different for different situations. But before diving into all of the details of HOW, answer to yourself (not your spouse, your team or investors), “What do I want to do”.

Explore everything. Then accept the odds and make a call.

I mentioned at the beginning, that the slope of the learning curve in the descent can be just as steep as in the ascent. More than any other period, the clock is running against you. Every day you don’t make a call, your team is left wondering, you’re burning valuable cash and worst of all, you’re a sitting duck, rudderless and directionless. So like everything else, you need a plan. Set a 2–3 week timeline to explore everything you need to — pivot, acquisition, shut down. If you’re lucky, you’ll have 1–2 others on your team that you trust as a sounding board but also to keep the ship running as usual while you go chase these options down.

Talk to everyone whose opinion you value — weigh their thoughts against what you want to do. Then at the end of that couple week period, sit down, see what you have, and make a call. Again ideally you have one or two people on your team that you trust to run this by, but don’t expect to get affirmation. This is an impossible situation for them. Affirmation is nowhere to be had. At most, you can get support for how you’re seeing and making the call.

Last thing: be brutal about the odds. Acquisition is a particularly hard one. There were many encouraging conversations that made me want to continue exploring. But when I looked at the data — were they in a position to acquire, had they done any/ many before, what would it be like to work with/for them, the odds became so impossibly long. Sure there might be the magical, miraculous offer but unless you have established relationships, it’s going to be unlikely. You have to fit into their priorities, their timing. If you don’t figure into them prominently and don’t have a lot of time, they’ll just be able to string you along until you’re dead. So beware. (Also, perhaps a side point to create and nurture relationships with possible partners along the way. But even then, hardly a guarantee.)

Call it kindly and do the right thing.

If you end up where I did, with the decision that a pivot would be unlikely (on the runway left, cutting 80% of team, and shuttering existing service for users) and that acquisition wasn’t going to happen with the most likely/ attractive partners, and that calling it was the right thing, then I urge you to do it quickly and do it kindly. How you act in the end, for these weeks, will cement how you’ll feel about it forever, and more importantly to me, it will influence what your future holds.

There were 12 days between deciding to call it and when we announced to our users. In those 12 days I talked to our investors, I told my full team and we worked on the product and communication plan that would see us through this process.

One common question I’ve gotten is: what did your investors do/say? Did they pressure you in any way? And I have to say this — I am so very grateful for every one of my investors. Not for one second did I feel anything but supported. First of all, having done monthly investor updates, the news didn’t come as a surprise. But even then, sending an email or calling them up to say that I was deciding to stop was excruciatingly hard for me. It’s not in me to give up and it very much felt like giving up. It felt like failing their faith in me, beyond the funds they had invested in me, and this vision. But almost to a one, the response back to me was: I’m sorry, I know how hard this must be for you — you certainly gave it your all. Now, what’s next?

I was hoping for understanding but these responses floored me. They also bolstered me for the rest of the hard to come.

So I will say this: I have always tried to treat my investors as an extension of my team — in taking their money, in regularly updating them and in respecting their faith and capital with honesty. I am so glad I did that because it made this part of the process as positive as it could be.

Next, employees: No contest, this was absolutely the hardest for me. These 11 beautifully talented people poured their everything into making Poppy into what it was. They walked away from bigger paychecks and cushier lifestyles to do this hard thing together. And man did we have fun. God, I loved working with this team. Waking up not knowing what challenges the day would bring but that it would be in solidarity and in feisty joy.

For these people, I was the one to kill the very dream that I had handed to them. It’s a brutal position to find yourself in. I very much felt like I was failing and giving up on them. But, and here’s the incredible, incredible thing: even after telling the team that they no longer had jobs, every single one of them showed up on the day we announced to our users. Because that’s what this team does.

Part of the reason that I decided to do everything so quickly was so there would be something to buy a bit of time for them. There certainly was no financial “upside” but I needed these talented people to have a bit of time to decompress over the holidays and then find the next thing they were super into. So if you’re in a similar place consider how to make a hard thing just a touch less so.

And finally users. This was going to suck no matter how we did it. Building a product that became such a mainstay for families and caregivers was an incredible honor and privilege, but telling them it was no longer going to be there was killing me. I know what it’s like to be left in the lurch and not have options — I was now going to be taking away the thing they relied on.

But here’s where we still had choice. Even though it would be harder and would be work while we were grieving, we choose to find every way to soften the blow. I talked to two leading competitors to get offers for families and caregivers to use their platforms instead. We worked on a plan to connect families and caregivers directly so they would still be able to work/ get coverage. We did this because we felt like it was the right thing to do and we wanted to act in the end as we did throughout the life of our company. We did everything we could. It was still painful and hard. But we could stand by the fact that even in the end, we would work to make it right. And though I had hoped for it but couldn’t expect it, our users came back to us with devastation, yes, but also love and support and above all, gratitude.

So through all that, here’s what it boils down to: even in the end, maybe especially, in the end, the most powerful thing you have is choice. The power to decide and dictate how this is all going to go down.

Maybe it wasn’t the way I envisioned Poppy to go. But so little of it was. And I am proud of how we ended up being the grace within the fire.

This venture was a deeply personal part of me. This team was an extension of my family. I gave everything I had for this mission.

Yes, this an end. There was much to learn from it. But it’s not THE end. There is so much power in knowing it’s within me to see a thing, start a thing and do a thing.

This end was hard but I also learned so much. I also learned the most powerful lesson: there is nothing to be feared in the end. There is no boogeyman.

I am bigger and more powerful than the fear and the illusion of failure.

I will keep these lessons near and dear, in the hopes that I don’t need to use them again, but in the faith that they fuel my next beginning.