What do you do when your best ideas fall flat, your clients say no to clear wins, and your carefully planned systems still lead to failure? If you’re Trevor Longino, founder of CrowdTamers, you treat it all as part of the job—and part of the process. In this conversation on Keep Going, we talk through the messy middle of building something that works: the clients you have to let go, the business models you have to fix, and the mindset shifts that only come after years of getting it wrong. It’s not about perfection. It’s about learning, adapting, and showing up anyway.

Keep Going: Fail Early, Fail Loud

John Biggs · Jun 2

This week on Keep Going, I talked to Trevor Longino from CrowdTamers, a repeat guest and someone who’s made a career out of iterating through failure. Trevor doesn’t just tolerate failure—he plans for it. He opens every client engagement with a $100 ad test that’s

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Here are some key takeaways from our conversation:

Failure isn’t a single event—it’s a process.
Trevor breaks down failure into stages. The lesson you learn one month after a mistake isn’t the same as what you learn a year later, or five years later. Each new perspective adds depth to what went wrong and why.

Iterate fast, fail small.
At Crowd Tamers, Trevor runs $100 test campaigns designed to fail. The goal isn’t to win early—it’s to find what doesn’t work quickly, so you don’t waste time or money chasing the wrong thing...

Most people don't think about engineering managers until something breaks. Code slows down. Tickets pile up. Meetings drag on. Then someone asks, “Who’s managing all this?”

John Kennedy, CEO of Actual AI, knows that problem better than most. He’s building software for the people holding the tech world together — engineering managers who plan, coach, and report across teams but are often stuck doing it with duct-taped dashboards or a dozen browser tabs.

I talked to John on Startup Show about why Actual AI isn’t just another dashboard or bot. It’s an agent. It sees code changes, turns them into business summaries, tracks developer velocity using Stanford-grade metrics, and cuts out the grunt work that usually drags teams down. Not by flooding your Slack with hallucinated code reviews, but by actually working — quietly, usefully, and consistently — in the background.

He told me their biggest goal is giving engineering managers their time back. Not with chat prompts or half-baked integrations. But by building something custom-fit: a true system of record for real-time development. The endgame? Let managers coach their devs, not babysit them.

It's not flashy. It's not buzzwords. But it’s exactly the kind of thing that matters if you’re trying to build something real and not fall apart halfway through.