Our Story

How to pivot your startup

Ian Yanusko
July 13, 2023
min read

Turn back the clock to January 2022, and the Bracket team was working on an entirely different product. We applied to (and got into) Y Combinator with a fintech product for content creators, but five days into YC, realized that our low traction was a good reason to pivot. Thus began five weeks of pivot hell, which had plenty of lessons to teach.

The goal of this post is to drop some resources we found helpful and share the hard lessons we learned.


- Jared Friedman on how to get startup ideas

- Paul Graham on schlep

- Dalton Caldwell on pivoting and quickly evaluating ideas

- Our framework

Our process

First, we tried to soft pivot. We took our original idea (pipe.com for content creators) and tried to apply it to athletes. Then we tried to do anything in the creator space. Then we decided to do a hard pivot, leaving the creator space behind.

We sat down for a whole weekend as cofounders and told our life stories, especially focusing on problems we faced at our old jobs. This helped us figure out good discovery questions. It also made us closer as founders. This got us to ~70 problems on the whiteboard.

We messaged a ton of companies in our YC batch who were building things that most interested us, explained we were pivoting, and asked for 15 minutes. We reached out to almost half the batch and met with ~80 companies. The ease with which we could meet with so many great companies in a short amount of time is one of the great benefits of YC.

We ranked every problem we heard by its intensity, frequency, and our perceptions of people’s willingness to pay. The goal here was to find a hair-on-fire problem, regardless of the solution.

We then brainstormed solutions to the top problems and ranked those solutions by founder-market fit, how easy it seemed to get started, and how easy it would be to get customers 1-10. We also did back-of-the-envelope market size calculations. You can see our framework here.

We pitched these to our YC partners, who helped us avoid any tarpit ideas.

Mistakes we made

We should have done a hard pivot from the get-go. We wasted two weeks trying to force-fit our previous solution / industry because of sunk-cost fallacy. A soft pivot may make sense for some companies, but it did not make sense for us.

We didn’t focus on our own pain points as early as we should have. It’s always better to be your own product’s user.

We listened too much to VC twitter, which led us to conferences we shouldn’t have attended in industries we weren’t passionate about. There are few things worse for a pivoting founder than VC twitter.

We kept thinking of solutions, which led us to qualify problems based on our limited perceptions of the “business potential.” Don’t do this! Just get good problems, then figure out the compelling solutions.

In discovery calls, we would drop leading questions to positively affirm whatever the idea of the day was. We were asking people to speculate on their behavior, rather than focusing on their past behavior and the preferences it revealed. We finally learned that the goal of discovery is to be a scientist, not a lawyer.

Most importantly, we tried to validate ideas rather than quickly invalidate them.

Additional helpful learnings

If possible, focus on operations-light businesses. 

Think about sales cycle for the business: how quickly will be able to invalidate the idea?

Consider whether or not your customer would outgrow your solution: how does that change the market size?

What we chose to build

Pain point: data engineers are often tasked with getting data in front of nontechnical teammates. Often, engineers have to build internal tools from scratch, manually export data to CSVs, or set up high-maintenance data pipelines. 

With Bracket, engineers can set up simple one-way and two-way syncs with the tools that business users already rely on – tools like Google Sheets, Salesforce, and Airtable – to move fast and save money. 

Try it out for yourself here.