Catharine Montgomery

1: Origin Story

Starting a company was never the plan. My career was built in communications, working in-house and at agencies on campaigns across education, environment and labor rights. For a long time, that felt like enough.

Then came a set of experiences with systemic racism, in the workplace and across the industry, that made the gap undeniable. There were communities whose stories were being told badly or not at all. There were organizations that wanted to do better but had no framework for getting there. Better Together came from that recognition. My first venture was an attempt to build something the industry was missing. Getting it off the ground meant raising capital, and for a while, it felt like proof the vision was working.

2: The Cost of Capital

The most important lesson is one most founders absorb too late: alignment on mission does not equal alignment on control.

The investors who believed in Better Together at the pitch table had a completely different definition of success once capital was in. The company was mine in every way. The concept. The clients. The culture. But enough equity had changed hands that when disagreements came, the votes were not there to protect the direction I had built toward.

No amount of passion or proof changes that math. Read every clause before you ever need it. Nobody gave me that advice early enough.

3: Building on Your Own Terms

One rule was clear before Better Together Agency launched. Ownership stays with me.

That came from hard-earned clarity about what gets lost when control changes hands. Watching someone else steer a company you built toward a direction you did not choose makes you very specific about what you are and are not willing to trade for capital.

That accountability has made the work better. There is no outside pressure to compromise the values underneath every campaign and no ambiguity about who is responsible for them. That structure was a choice, and it was the right one.

4: AI as a Foundation

AI is not a feature at my agency. It is infrastructure.

From research to strategy development to TogetherAI, a private bias-aware AI platform my team built for campaigns, the technology is woven into the actual work. The biggest difference has been capacity. A small team can now operate at a scale that once required a much larger operation, without losing the strategic depth clients come for.

They automate tasks without asking whether those tasks should exist in the first place. The deeper question, one very few founders ask, is whose assumptions are baked into the models they use every day. My annual Biases in Generative AI survey, conducted with 1,010 U.S. adults, found that 92 percent of consumers believe companies must address AI bias. That is a business reality, not a footnote. Founders who skip that question are building on a foundation they have not examined.

5: The 2x Founder Lens

Separate the loss of the company from the loss of yourself. Those feel like the same thing when you are inside it. They are not.

Processing what happened with Better Together took real time. Trusting my own instincts again took even longer. But losing that company did not make me less capable. It made me far more specific about what to build and why.

Ask what this moment is actually teaching you about the decisions that led here and the ones still ahead. That answer is where the next company lives.