Reflections on -1 to 0 and Exploring Ideas

Reflections on the -1 to 0 phase of exploring business problems and ideas

Nov 03, 2023

I wrote this to capture the lessons I learned navigating the exploration process 4 years ago to ultimately build Songbird. Since it’s a live document and I don’t know how frequently I’ll update this post, I’m also hosting it here. Please reach out to me if you have comments/feedback, especially if there are points you have a different take on. Thanks for following along!

The infancy stages of starting a company are some of the most challenging. If the 0 to 1 phase is building out the idea and getting initial customers, the -1 to 0 stage is the winding maze to figure out what idea to pursue.

The -1 to 0 stage (aka idea maze) usually breaks down into 3 components: generating ideas, validating ideas, and gaining conviction.

First, you generate ideas. You may have started with a specific idea, but it is rare for the first business idea someone has to work out perfectly, or for that idea to remain constant. More commonly one realizes flaws in the idea, and needs to figure out how to iterate on it or explore new paths.

Second, one must validate their idea, ensuring that it solves a real need. This often runs somewhat parallel to building an MVP and obtaining initial customers. Validating ideas is important because the most common startup mistake is not building something people want.

Third, at some point you must gain (and maintain) conviction in pursuing an idea. Conviction is the will to keep going, and is tough. Your conviction will be challenged when you’ve left your job, are 3 iterations past your original idea, and have no traction on the current one.

Having gone through this process once and now working on some new ideas, here are some of my thoughts for others going from -1 to 0.

Retro on Songbird exploration process

What we did well

Evaluating a large number of ideas - We explored about ~40+ ideas (writing up, spending at least a couple of days, MVP-ing or talking to customers). This helped us calibrate and understand what good looked like.
Iterating fast - We utilized mockups and no-code MVPs to prototype quickly. We were mostly decisive and quick to kill an idea or pivot.
Using personal interest to drive unique insight - We spent the bulk of our 9 month full-time exploration pulling a thread in special needs and children’s behavioral health. That led us to the then-niche space of ABA, which wasn’t something many other people were working on.
Building something people wanted - We were very focused on solving a hair-on-fire problem and ensuring there was a clear path to revenue. This led us to solve what was a deep problem (access to care for children with autism) and eventually build a meaningful revenue scale business.
Structured day-to-day process - We heavily documented our process: weekly task lists, 1-pagers, hypotheses/risks, retros. Even 4 years later, I can easily follow our thinking during that time (and also see what assumptions later went right/wrong).
Creatively sourcing customer and expert calls - I estimate we interviewed >100+ parents of children with autism/behavioral health challenges, >100+ from other user groups, and >50+ experts/stakeholders in spaces we were exploring (via LinkedIn, Craigslist, personal network).

Opportunities for improvement

Find a way to be more patient - 6 months into full-time exploration (around March 2020) I remember feeling anxious to figure out what to pursue. I don’t think this causally led us to pursue a bad idea, but it was unpleasant. Patience and time is needed to develop the insight that makes up a good idea, so it’s worthwhile to figure out what you need to feel that. For example, starting a side business or consulting can extend personal runway and give you projects to work on while exploring.
Assess key risk of your “type of business” - We focused on the level of customer need as the risk for the tech-enabled ABA business, and should have spent more time on margin/financials (analysis akin to what private equity investors do). While it’s dangerous to be revisionist about history I believe that would have led us to 1) evaluate the quality of opportunity differently, and 2) pursue the opportunity in a savvier and more financially-minded way.
Founder-market fit - I wish we had anchored 1-2 levels more on our own unfair advantage: our experience building digital/software-based products. (The flip side of this is that we were first-time founders 2.5 years out of school, so there wasn’t too much that was an unfair advantage outside of being technology oriented). Still, unfair advantage matters.
Prefer bootstrapping over starting a VC-backed business - Venture capital can be a useful tool to capitalize solutions to a certain type of problem. But it’s easy in Silicon Valley or related communities to forget that the aim should be to solve a problem you care about and have an unfair advantage in. The vast majority of businesses (even technology-oriented ones) don’t require too much capital.
(A little) Less breadth - I would have spent less time on spaces like creators and future of work, and more time on our actual interest in children's behavioral health. 4 years later, it looks like many other ideas we saw are potentially viable businesses. The lesson here is that within any big market and real problem, there are many opportunities (may or may not be venture-backable). Focus on a market or problem breeds unique insight that is transferable to similar ideas.

Generating Ideas

If you’re not ready to take the plunge, then work somewhere that will give you relevant experience

If you want your Next Next Job to be starting something, then be intentional about how your next job will bring you there. (Andrew Chen’s Next Next Job framework)
Working at a large company can help you identify an internal tool to “export” (Graphite exported stacked diffs from big tech companies) or a problem to “import” a solution for (MFM podcast).
If you want to start an industry-specific company (like in healthcare), then working at a company in that industry will give you unique insight into customer needs.
Or, just find a talent-dense company where you’ll meet other entrepreneurial people.

Burning the boats is destroying all possible ways to go back to a situation e.g. quitting your job to start a business

Quitting your job to go all-in, even without an idea, can be a rational decision if 1) you feel like you will benefit from the urgency it creates 2) you have a reasonable plan for personal runway.

Start with problems you’ve experienced or have a unique tie to

A lot of people in the -1 to 0 stage explore ideas they think might be good businesses, but they have no prior experience or personal interest in.
This is dangerous because you easily end up pattern-matching and applying business model heuristics (Uber for Zebras) instead of identifying a problem or solution from an angle of unique insight. This approach also tends toward breadth (surface-level exploration) vs. depth.

You will have more success the more your ideas are aligned with your unfair advantage

Unfair advantage can be a personal life experience, a problem you experienced, networks of people you know, types of products you’ve built before
A helpful heuristic is to ask yourself “why should we be the ones to start this idea?” (caveat: just a heuristic)

Consult to manually solve a problem that you can later productize into an offering

Consulting allows you to confirm that a problem exists and test ways of creating value (consultative sales is also a very effective approach to selling something)
If your goal is to start a business, then you will want to be careful about choosing projects when taking this approach, else you’ll loan out your time for income forever.

Focus on one or a small number of markets and problem spaces to develop a unique perspective

Depth is important because new and interesting ideas tend to be at the frontier of a field.
“Once you've found something you're excessively interested in, the next step is to learn enough about it to get you to one of the frontiers of knowledge. Knowledge expands fractally, and from a distance its edges look smooth, but once you learn enough to get close to one, they turn out to be full of gaps.” (How to Do Great Work, Paul Graham)

Talking to hundreds of customers and people in your space

Before I left my job I had ~140 conversations with folks in the mental healthcare space to understand how the system worked, since I had never formally worked in the field. Later we had ~100+ conversations with parents of children with autism and other relevant stakeholders to land on the autism therapy idea.
Doing it again, there was probably an opportunity to be more targeted. But when you’re early and new, talk to as many relevant people as possible.

Validating Ideas

Sell early and frequently: “Going to market with products is how you find PMF”

Lattice has a great story about how they originally built an OKR tool, convinced a CEO to try it out with their company, then learned through implementation with the HR manager that the real need was performance reviews.
“Going to market with products is how you find PMF. It’s the act of going to market that helps you see what people want.” (Jack Altman on Lattice on Invest Like the Best)

Avoid the distorting effect of hype. Niche/weird spaces often can be better businesses because competition erodes business quality

Areas have hype for a reason, but hype can be dangerous because you mistakenly attribute opportunity due to hype and not first principles.
Hyped areas also have way more smart competitors competing for the same pie. Competition is for losers.

You can save yourself tens of hours of work by talking to an expert who has tried your idea before or built a similar business

There are 31 million entrepreneurs in the US and most ideas (or some variant) have been tried before.
Be careful to stand on the shoulders of their knowledge, but not necessarily follow their prescription about whether it’s an idea worth pursuing.

Evaluating your opportunities using a standardized framework can make this process less emotional and more rational

The path from ideation to conviction that an idea is worth pursuing is inherently unstructured.
When building Songbird, we used a business canvas for “Total Conviction,” which included criteria like: success selling a prototype, having validated the concept with smart friends, and having a why now.
Note: this framework was based on our desire to start a venture-backable company, so if you’re not aiming to do that your evaluation criteria will be very different.

Write out specific risks and align your validation activities with them

When exploring an idea, I force myself to write out the top 3 risks for why this might not be a good idea.
Often the top risk is related to not solving a problem or there existing willingness to pay, but for some healthcare service ideas it might be unit economics or margin.

Prefer manual/lightweight prototypes over building something

One of the most common situations in the tech startup community is a team which has spent 3-6 months developing a prototype, only to realize nobody wants their product.
Many ideas can be validated with zero or little development: LOIs/paid pilots/design partnerships for business software, painted-door tests with some paid advertising for consumer, 1:1 sales, starting a community, delivering a service manually.
And if you really do need to build something, then scope it small and intentionally.

For B2B, put together a customer advisory board

My friend Matt Schulman of Pave put together a customer advisory board of enterprise HR leaders to get feedback on and validate his HR/compensation software idea.
An advisory board can increase your conversion rate to meetings with your prospective customer, and provide a mechanism to establish a longer-term relationship that might evolve into a paying customer.

Motivation & Other Thoughts

Be clear about the game you are playing

Know whether you’re playing the bootstrapped or venture-backed (or other type) game. Nowadays, it’s easy to get caught up in broad visionary narratives like “transforming industries.”
Being clear about this will determine the scope of ideas you explore, what criteria should be in your evaluation framework. For example, starting a bootstrapped/non-venture company opens up the scope of ideas that fit this criteria.

Develop and stick to your own semi-structured process

The -1 to 0 progress is not linear. The north star of “conviction on an opportunity to pursue” is inherently abstract. Each idea that you invalidate will feel like a failure, and it’s easy to feel demotivated.
Lightweight process can help you feel momentum amidst the uncertain ups and downs. For example, we’d write a “Week Plan” doc on each Monday and then retro at the end of each week to checkpoint progress.
Also, goal-ing on an intermediate metric like # of ideas validated or invalidated can drive a sense of progress on the inputs that matter. My friend Parthi shipped 12 functional products before deciding to pursue Letterdrop, a MarTech platform for content marketing automation.

Optimistic about the opportunity to solve problems, skeptical about individual ideas

Folks who quit their jobs to start something are by nature optimists - I know I am. Counterintuitively, a healthy amount of skepticism about your own ideas can be useful to avoid leaping into working on something that won’t go anywhere.
Note: This advice is for ideas that you hope to turn into a more full-time business (bootstrapped or venture-backed), but isn’t as applicable for “small bets”-type projects. For those, the cost to build and launch is much smaller.

Have patience; ensure that you fish in the right pond

There was a period of 8-9 months between leaving my job in October 2019 and gaining conviction on Songbird in mid-2020. Many folks told us we spent too much time in this phase, but ideas matter and choosing what to work on is one of the highest leverage decisions.
Figuring out ways to give yourself time can help ensure that you work on the right thing (working a job, consulting, smaller income streams).

Every heuristic here will invariably be disproven; reason from first principles

Heuristics need to be applied in context. The advice here is more useful for healthcare, marketplaces, B2B, SaaS and likely much less for frontier tech, consumer social, highly technical business ideas.
There’s no one path to building something successful, and probably the only two axioms are working extremely hard and reasoning from first principles.

The -1 to 0 stage is a unique place to be. You have full freedom: to explore any opportunities and paths you might want. And it’s highly leveraged: the choices you make now will substantially impact the flavor of the next couple of years of work. Good luck.