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Startup Therapy

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Startup Therapy

Startups.com

Where were you when I was broke?

June 30, 2026 10:29am 48 min

Ever notice how people show up loudest after you’ve already won? This episode digs into why founders often get the least support when the risk is highest—and the most opinions once success is “de-risked.” Will shares ear...

What if I'm the Best, but don't know it?

June 23, 2026 8:51am 54 min

What if building a company is the fastest way to find out what you’re actually capable of? This episode explores how startups don’t just get built by founders—startups build founders by forcing them into new roles like f...

Founders Don't Retire

June 15, 2026 8:35am 33 min

What if “retirement” for founders isn’t about stopping work, but finally getting relief? The conversation unpacks why builders rarely stop building: founders are wired to create, not to consume, and the fantasy of beach ...

The Right Time to Start is Right Now

June 08, 2026 11:00am 38 min

Ever feel like you’re “almost ready” to launch—just one more feature, plan, or credential away? This episode argues that “ready” isn’t a prerequisite for startups; it’s the result of starting and getting real market feed...

The Most Expensive Equity Doesn't go to Investors

June 01, 2026 9:21am 46 min

Why do founders fight over giving an investor 15% but hand out huge chunks to co-founders, employees, and advisors with far less certainty of return? The episode argues that investor dilution is often the cleanest trade ...

How to be Great at Worrying

May 25, 2026 11:00am 35 min

Ever wake up at 3:00 AM convinced your startup is about to break? The conversation unpacks how founders can’t really “leave work,” and how constant vigilance can turn into fear dressed up as responsibility—endless rumina...

Can Startups Be a Team of One?

May 18, 2026 10:36am 43 min

What happens if building a startup no longer requires a team? The conversation explores how AI is rapidly turning the classic “product + developer + marketer” founding trio into an optional choice, making one-person comp...

Why are we Really Building a Startup

May 11, 2026 8:26am 33 min

What are you really trying to fix by building this company—and what happens when you finally admit it? The conversation unpacks how founders often default to a public “change the world” story while their private motive i...

We Rarely "Control" Our Startups

April 13, 2026 11:00pm 46 min

Worried about “losing control” because of dilution? This episode breaks down why equity is a poor proxy for control in startups: the cap table splits money, while control is defined by decision rights in the operating ag...

Founders Need Finish Lines

April 06, 2026 9:31am 38 min

Ever feel like you hit a milestone in your startup and immediately get handed the next problem? The episode explores why startup work rarely delivers a true sense of “done,” how founders get trapped by the arrival fallac...

What Should My Expectations Be?

March 23, 2026 11:00am 47 min

Ever feel like you’re working nonstop and still falling behind? The discussion argues founder happiness and decision-making improve fastest by recalibrating expectations, because “happiness = reality ÷ expectations.” Usi...

What Actually Happens When A Founder Runs Out of Gas?

March 02, 2026 8:21am 34 min

What do you think really happens if you burn out and step away for a minute? The conversation breaks down how founders often imagine an apocalyptic chain reaction—customers leaving, the team collapsing, investors panicki...

The Value of Distraction

February 23, 2026 9:03am 35 min

What if the thing that looks like a distraction is actually the move that saves your startup? This episode breaks down why the “stay focused at all costs” advice can be risky when you’re still figuring out what actually ...

Master Failure

February 16, 2026 6:19am 36 min

What if failure isn’t something to avoid, but a skill to master? This episode breaks down why startups can’t be built on certainty—new markets, new products, and new teams mean you’re guaranteed to be wrong a lot. The go...

We Can't Predict the Future Anymore

February 09, 2026 7:38am 37 min

Is AI truly the game-changer for startups, or does it bring unexpected chaos? This episode dives into how AI is transforming forecasting, marketing, product development, employment, and investment in the startup ecosyste...

We wanted efficiency. We got isolation.

February 02, 2026 7:02am 41 min

How has the relentless pursuit of efficiency, aided by tools like remote work, Zoom, Slack, and AI, affected our human connections? In this episode, we're exploring the cost of optimized workflows on our humanity. We del...

Are startups the future of employment?

December 03, 2025 6:51am 47 min

What will AI do to everything? In this episode, we explore how AI is set to create a surge in new startups, reshaping employment as we know it. As jobs get displaced, the concept of big employment shifts, giving rise to ...

The Founder Hard Reset

November 25, 2025 6:49am 25 min

Ever felt like vacations just aren't cutting it when it comes to startup burnout? In this episode, Ryan Rutan and Will Schroter dive deep into why burnout is inevitable for founders and how quick fixes like vacations oft...

Is there a line between Founder optimism and delusion?

November 17, 2025 11:00am 37 min

Can founders turn delusion into success? In this episode, Ryan and Will discuss the essential role of optimism in startups. Drawing parallels between founders and firefighters, the duo explores how belief against all odd...

Prioritize Productivity Over Popularity

November 07, 2025 5:07am 31 min

Ever find yourself caught in the trap of confusing visibility with progress? In this episode, we'll delve into why seeking attention can often feel like momentum but doesn't necessarily translate to business traction. Wi...

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