Stop Hiring to Solve Big Problems You Don’t Understand Yet

by | Mar 28, 2025

Most new founders have it backwards, believing you hire people to solve the big problems in your business.

But it rarely works to hire someone to solve a complicated problem you don’t understand well yet.

You need to understand it well enough to start fixing it before you hire someone to solve the rest of the problem and take it over.

If your software startup has explosive growth, this hire-to-fix problem is multiplied.

Rebecca Shostak is co-founder and chief brand officer of Flodesk, the popular email marketing software for small business owners who care about beautiful brand design.

After prototyping the product and validating the problem, they launched in 2019 with a viral explosion that still powers their bootstrapped growth.

They have been profitable since the second week after launch, driven by great product design, the email footer “viral loop,” and referrals from customers and influencers.

Six years later, Flodesk has over $30M in annual recurring revenues, with 75 employees and over 100,000 paid customers.

They never outgrew having big problems to solve, but the cofounders quickly learned the better way to hire:

“The reason you hire is never to solve a problem. You need to be sharp and figure out how to solve the problem on your own. Then, you hire people once you’ve proven something.

“When you want to hire someone to run your paid ads, for example, you first need to figure out the basics and get a good return on investment. Then, you can hire someone to come in to own that so they can scale that operation.

“It doesn’t work to hire someone to come in and figure out something that you can’t figure out yourself. How can you hire someone to manage something you don’t understand?”

In this episode, Rebecca shares her deep insights on software product design, their unlimited pricing model, working with her co-founder/CEO, Martha Bitar, why they haven’t taken outside funding, and where AI is showing usefulness in their products.

Check out this revealing interview with Rebecca Shostak on the Practical Founders Podcast. 

Greg Head posted this on LinkedIn on March 28, 2025.

Check out the comments and join the discussion on LinkedIn.

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