Growing a Business Beyond the Early Stage (and Where Cold Outreach Fits) — with Jonathan Grzybowski
Mon Feb 02 2026
What does it take to grow a business past its early stages? And how does your role change as the company gets bigger?
In this episode, Jonathan shares what it looked like to take his business from a very small team to a company of more than 500 people. He talks about the early days of building traction and how nearly 200 conversations helped shape the product, messaging, and direction of the business.
We talk about outreach as part of that growth — not as a formula, but as something rooted in persistence and direct connection with the right people. Jonathan shares what that looked like in practice and how those efforts opened doors to larger clients and wider reach.
The conversation also moves into leadership. Jonathan reflects on the shift from founder mode to leading a much larger organization, and what he’s had to learn about systems, processes, and decision-making as the company scaled.
We talk about how being a parent fits into all of this — the long days and the reality of continuing to build a demanding business alongside family life.
This episode offers an honest look at what changes as a business grows, and how the work of leadership evolves alongside it.
Penji Website: https://penji.co/
Johnathan’s LinkedIn: https://www.linkedin.com/in/grzybowskij/
Brittany’s Website: https://downeystrategy.com/
Brittany’s LinkedIn: https://www.linkedin.com/in/brittany-downey/
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What does it take to grow a business past its early stages? And how does your role change as the company gets bigger? In this episode, Jonathan shares what it looked like to take his business from a very small team to a company of more than 500 people. He talks about the early days of building traction and how nearly 200 conversations helped shape the product, messaging, and direction of the business. We talk about outreach as part of that growth — not as a formula, but as something rooted in persistence and direct connection with the right people. Jonathan shares what that looked like in practice and how those efforts opened doors to larger clients and wider reach. The conversation also moves into leadership. Jonathan reflects on the shift from founder mode to leading a much larger organization, and what he’s had to learn about systems, processes, and decision-making as the company scaled. We talk about how being a parent fits into all of this — the long days and the reality of continuing to build a demanding business alongside family life. This episode offers an honest look at what changes as a business grows, and how the work of leadership evolves alongside it. Penji Website: https://penji.co/ Johnathan’s LinkedIn: https://www.linkedin.com/in/grzybowskij/ Brittany’s Website: https://downeystrategy.com/ Brittany’s LinkedIn: https://www.linkedin.com/in/brittany-downey/