Founder-market-aspirations fit ⛷💰💭
A serial founder figuring out what (not) to create next, pivoting to a less “risky” yet more impactful venture, and the exacting work of building on top of platforms.
Welcome to the fifty-fourth edition of The Baton. A fortnightly newsletter that brings you three, hand-curated pieces of advice drawn from the thoughtful founder-to-founder exchanges and interviews taking place on Relay (curated with 💛 at Chargebee) and the interwebz. So, stay tuned!
In this edition, you’ll find instructive and inspiring pickings from the brains of (#1) SavvyCal’s Derrick Reimer, (#2) Momento’s Khawaja Shams, and (#3) Boomerang’s Aye Moah.
Recently on Relay:
Heuristics and Hunches — “How Moving Away from Per-User Pricing Helped us 4X our Growth, Why We Were Moving Back, and Why We Won’t (For Now)” with Tability’s Co-Founder, Sten Pittet
Heuristics and Hunches — The Why Behind 78 Pre-Product User Interviews, The Difference Between Pitching and Research, and Why MVPs Don’t Work Anymore with Cord’s Co-Founder, Nimrod Priell
#1: “My process for narrowing down what to build next” — SavvyCal’s founder, Derrick Reimer, lists some of the attentive filters he deployed for arriving at his next bootstrapped idea; a personal sieve projected outward to net real founder-market fit. (Source: Derrick’s blog)
Most business ideas are neither objectively good nor bad. The quality of an idea for you (as a founder) depends on your goals, your skill set, and your risk tolerance.
Even the quintessential lousy idea of trying to “build the next Facebook” is not necessarily a bad idea. Someone will eventually pull it off – it just comes with an enormous amount of risk and requires one hell of a skill set.
So given a list of potential ideas, how should one go about picking The One?
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Before trying to establish my filters, I need to understand why I’m doing this in the first place.
Do I want to change the world by creating innovative new products? Do I aspire to make a life-changing sum of money and retire early? Am I just tired of working for someone else?
My primary motivation is to earn a comfortable living for my family, with a bit left over to fund causes for which I have a passion. I want to achieve predictable product revenue that does not directly correlate with the number of hours I work.
I want the freedom to build products that are interesting to me as a maker. I love to strategize, design, and create. I don’t enjoy managing people. Eventually, I want the ability to take a month off of work without negatively impacting the business.
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[My filters look like this right now:]
Since I want to bootstrap my next venture, the market must already exist. There should be competitors attempting to serve the market (but perhaps not doing a great job of it).
I’m relatively risk-averse, so an MVP must be shippable within a few months. It’s hard to know upfront if this is possible, but I can confidently eliminate ideas that I know will take a long time. The product must be valuable to a particular niche, even when it’s new.
The product should not be mission-critical. By mission-critical, I mean so vital that even a short period of downtime will have a significant impact on my customers’ businesses.
Making a sale shouldn’t require more than a few decision makers. A counter-example would be a product like Slack, which requires buy-in from every stakeholder in a company to adopt.
Native apps should not be a minimum requirement. These days, users have come to expect native desktop and mobile clients for specific categories of applications (communication, project management, and note-taking, to name a few). It’s hard enough building for one platform as a small operator, let alone three or four platforms.
Since I regularly invest in growing my following on Twitter and my weekly podcast, the market should overlap with my existing audience.
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There is no perfect business idea, and I may have to compromise on some of these criteria – that’s okay. I expect these to evolve as I gain more clarity.
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No business exists in a vacuum. There will always be parts that keep you up at night – but hopefully not too often!
#2: “You don’t want to pivot for the sake of pivoting” — Momento’s co-founder and CEO, Khawaja Shams, recounts how a confident, self-determined constraint led them adrift and how they found their way back with a pivot. (Source: Engineering Founders)
One of the constraints that we put on ourselves was to not be constrained by domain expertise. We wanted to be brave and bold.
Our initial idea that we ended up picking was in the consumer space and if you know anything about Daniela’s background [Former Director of Engineering, Lightstep] or my background [Former VP of Engineering, AWS Elemental] you’d see that we had zero expertise, zero domain experience in building consumer products.
But we did not let that deter us. We really fell in love with this constraint…
And, unfortunately/fortunately that led us to over-index on it and pick something that was really not in our domain expertise because we were always curious about what it was like to build a product in the consumer space.
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You don’t want to pivot for the sake of pivoting. You want to make sure that the particular idea that you’re pursuing, you’ve given it a fair shot. You’ve tried everything. And you have the right success criteria that you have defined.
Because before you hit the success point you’re inevitably going to have a bunch of disappointments to deal with on your way to success…
If things aren’t going well, ask yourself why and don’t use pivot as the natural answer necessarily. Keeping that in mind, for us it was just our ability to disconfirm our beliefs.
We were really passionate about this idea [a social fitness app] but we were vocally self-critical that a) we weren’t getting the adoption that we expected us to be getting and we weren’t getting closer to getting it, and 2) we weren’t becoming the experts in the particular, new field that we were in despite working really hard for months…
That notion that we weren’t getting better and that we weren’t getting the expertise we needed to really differentiate us from every other person in that space, made it a little bit easier for us.
So, disconfirm your beliefs, set concrete criteria ahead of time, and value yourself against them and ask yourself why you aren’t meeting them.
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Bluntly, we were failing. We failed to raise money. Many investors were very generous with their time. They would take our calls. They would hear our idea very politely. They’ll say: ‘yup, we like the idea, we like you, you should do something different.’
We didn’t realized that investors are going to be taking meaningful risks on us and founder-market fit is a pretty good de-risking facility that investors really like. And for good reasons. It’s a rational thing.
It took us time, but we eventually realized that we are not the domain experts in this and in some cases, we learned that the investors knew more about the space than we did.
That’s a bad sign. That’s a great thing for an entrepreneur…but it’s a really difficult position to put the investors in. So that was one thing.
The second thing was that the app that we were building when we compared it against the state of the art, vs what we had imagined, we just weren’t making as much progress. It didn’t feel as different as our previous, arrogant selves thought that we could make it.
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On 90% of our investor calls, they’ll say: ‘This is nice. Not interested. If you do something in the infrastructure space just let us know.’
Some of them were just hinting, ‘you have this big opportunity why aren’t you taking it.’ And then, one of the investor contacts that Daniela had actually gave us a pep talk:
‘Take the biggest thing you can take and find your unfair advantage. You are no more uniquely qualified to do this than a random student at Stanford, for instance. What makes you uniquely qualified to do this particular consumer startup?’
And we couldn’t answer this question…We thought about it and we kept answering it to ourselves and we just were never happy with the answers we gave ourselves.
Those were the kind of signals that led us to say, ‘alright, let’s see what else we can be doing, let’s go back to our list.’
#3: The ever-demanding work of building browser extensions — Boomerang’s co-founder and CEO, Aye Moah, speaks to the compounding “layers” of upkeep that extensions (and platforms) require and what that means for new entrants. (Source: Going Deep)
An extension developer’s life is really hard. If I see a new entrepreneur, asking me, ‘hey, Moah, I want to talk to you about this new extension I’d like to bring,’ and I’m like, ‘hey, are you sure you want to do this?’
Because you’re at the mercy of multiple layers of controls and systems that are not quite logical. And may not be the top priorities for those companies.
So you’re always keeping up with different policy changes. ‘Hey, Safari is changing their API to this and is going to be deprecated in three months.’
So we dedicate December, the whole month of December to this. We don’t do any new product development to just keeping up with all kinds of changes that everybody is bringing.
From Python language changes to Chrome Web Store is going to require these new things, to Gmail API is going to need this. Outlook is doing this. All of that… One out of every 12 months, we have to resource everybody on that. That’s just to keep alive.
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When we first started, it was just a wild west, anybody could put whatever they want. Put it out there. Everybody is installing. Access to [their] Gmail inbox. And there were some shady businesses that came out of that…
Now Gmail has a very strict security process that we have to pass every year. To actually go through and get certified by them. To know that we’re handling their data respectfully, securely, and not doing any shady stuff.
That, in a way, is a little bit tougher for the new developers that are coming in. Because that takes a lot of understanding and monetary resources to get through the process.
Until next time,