Startup Therapy

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 panicking—when in reality burnout is a predictable capacity ceiling and most worst-case scenarios don’t happen. They argue the real danger is pretending burnout won’t come, pushing until physical failure, and keeping recovery secret, which can create the chaos founders fear. Using sports analogies, they emphasize that staying “on the field” nonstop makes you a liability, and that planned breaks build resilience, give teams room to step up, and help founders regain creativity and effectiveness. The core takeaway: treat recovery like required maintenance, plan for it, and build a company that doesn’t depend on you 24/7.
What to listen for:
00:57 Apocalypse Scenario
02:12 Always On Mentality
03:49 No Built In Breaks
06:56 Superman Plan Fails
08:06 Burnout Warning Signs
10:32 Atlas Shrugged Reality
15:22 Hockey Shift Lesson
16:23 Fear of Replacing Yourself
16:46 Stop Guessing Get Help
17:19 Burnout Nightmare Myths
19:14 When Investors Shrug
20:57 Youre Not The Main Character
23:24 Let The Team Step Up
25:14 Breaks Prevent The Crash
27:06 Vacation ROI Mindset
29:34 Plan Recovery Like Taxes
31:44 Durable Not Tireless
33:22 No Great Company Empty Tank
Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/
Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

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 works. The hosts challenge the myth of the linear startup path, arguing that side quests—small, intentional experiments with capped downside—create learning, reduce single points of failure, and help you earn the right to pivot with evidence instead of vibes.
They share how Fundable’s early equity crowdfunding push revealed founders were unprepared to raise money, which led to a major side quest: doing diligence on about 100 companies, talking to 200+, and acquiring six venture-backed businesses—work that became the genesis of startups.com. Along the way, they highlight the value of the quest itself (market intel, understanding what not to do, faster learning) and even mention an extreme near-distraction: briefly considering buying Atari.
The conversation also reframes common “side quests” like doing services work while building a product, arguing that bringing in revenue to stay alive isn’t a distraction—it’s the business. They clarify the difference between a side quest (exploration) and a pivot (committing to a new direction), and point to the podcast itself as an example of a side quest that became a major long-term asset after a rough start.
What to listen for:
00:40 The AI Newsletter Moment That Sparked the Topic
01:47 What a “Side Quest” Means for Founders
03:45 The Myth of the Linear Startup Path
06:34 When Focus Becomes a Liability: Certainty, Ego & Roadmaps
10:04 Side Quests as the Ongoing Lab (and Why It Never Ends)
12:01 Case Study: Fundable 2012 and the Crowdfunding Gold Rush
15:48 The Pivot: Founders Needed Help, Not Just a Platform
18:07 Side Quests Done Right: Controlled Experiments (…and Almost Buying Atari)
18:42 The Wild Idea: Almost Buying Atari (Nostalgia vs. Distraction)
19:48 Why Side Quests Matter: Learning More Than the Outcome
20:42 Founder-Forward Deal Talks & Market Intel as a Force Multiplier
22:10 Side Quests as “Insurance”: Selling the Learning to Skeptics
23:48 The Classic Startup Side Quest: Services to Pay the Bills
27:14 Side Quest vs. Pivot: Exploration First, Commitment Later
27:52 The Podcast as a Side Quest That Became Core to the Business
30:26 Earning the Right to Pivot: Evidence, Courage, and Finding Truth
34:20 Closing: De-Risking Through Exploration + Startups.com Community Invite
Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/
Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

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 goal isn’t to “be right,” it’s rapid error correction: make decisions, ship anyway, learn fast, and recover even faster. The conversation covers how avoiding failure leads to paralysis (“steering a parked car”), why indecision compounds in startups, and how to reduce risk by keeping failures small, reversible, and frequent (kill switches, stop rules, and capped losses). They share early personal stories—school fights and a childhood cattle business collapse—to show how overcoming real consequences builds confidence and resilience. Practical examples include choosing an ICP quickly, improving poor conversion rates through iteration, using vesting/cliffs when picking co-founders, and why even top VCs still miss constantly. The key takeaway: the most dangerous competitor is the one who isn’t afraid to get hit, recover, and keep coming back—because that’s as close to “invincible” as a founder can get.
What to listen for:
02:01 Failure Isn’t the Enemy: Stop Optimizing for Being Right
02:59 The Founder Reality: Uncertainty, Rapid Error Correction & the Boxing Analogy
03:44 Safety vs Startups: Why Most People Avoid the Risk
05:24 ‘Steering a Parked Car’: Indecision Kills Startups
07:54 Make the Call, Learn Fast: Small Failures, Big Truths
09:02 We’re Conditioned to Fear Failure (School, Work, Relationships)
11:59 Will’s Origin Story: Jason Barker and Learning to Beat the Monster
14:48 Choosing to Fail on Purpose: Turning Fear into a Superpower
17:06 Ryan’s First Big Failure: The Farm/Cattle Business Lesson Begins
17:45 Cash-Strapped Expansion: Inventory Leverage & a Brutal Winter
18:09 When the Side Hustle Needs a Side Hustle (and the Cost of Neglect)
18:35 Failing Hard at 12: Losing Animals and Learning to Plan
19:51 Founders Don’t Win by Being Right—They Win by Taking Hits
21:36 Shipping While Wrong: Marketing Experiments, MVPs, and Momentum
22:51 Hiring, Co-Founders & Investors: Why Nobody Can Pick Perfectly
24:00 The Real Skill: Recovering From Failure (Resilience as a Reflex)
30:26 Small Blast Radius, High Frequency: Reversible Bets & Kill Switches
31:13 Failure Is Portable: Building a House, Living ‘Why Not,’ No Regrets
Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/
Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/

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 ecosystem. Ryan Rutan and Will Schroter discuss the rapid pace of change brought by AI, including the exciting opportunities and the unsettling uncertainties. They explore how traditional pillars of business like hiring, marketing, and customer acquisition are being upended, creating both new challenges and avenues for innovative founders to thrive. Tune in to understand how to navigate this AI-driven landscape and leverage the chaos for maximum impact.
Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/
Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/
What to listen for:
00:00 Introduction and Future Predictions
00:49 The Impact of AI on Business Models
02:06 AI's Rapid Advancement and Market Disruption
04:17 Challenges in Marketing and Content Creation
10:04 Hiring and Talent Management in the AI Era
15:18 Product Development and Market Relevance
17:04 Industries Vanishing Overnight
17:32 The Accelerating Pace of Change
18:20 Investment in the Age of AI
19:07 The Future of Startup Funding
22:31 The Shrinking Moat of AI
24:54 Compounding Anxiety in the Startup Ecosystem
33:37 Founders: Built for Chaos
35:53 Embracing the Problem Business

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 delve into personal anecdotes and discuss the ramifications of isolation in the workplace and the loss of shared experiences. We also contemplate the importance of reintroducing human interactions to ensure a balanced, connected, and more fulfilled work environment.
Resources:
Startup Therapy Podcast
https://www.startups.com/community/startup-therapy
Website
https://www.startups.com/begin
LinkedIn
https://www.linkedin.com/company/startups-co/
Join our Network of Top Founders
Wil Schroter
https://www.linkedin.com/in/wilschroter/
Ryan Rutan
https://www.linkedin.com/in/ryan-rutan/
What to listen for:
00:31 The Loneliness of Optimized Efficiency
01:48 The Impact of Remote Work on Human Connection
04:14 The Rise of AI and the Decline of Human Interaction
12:41 The Evolution of Remote Work Culture
17:20 The Dystopian Reality of AI Conversations
20:22 The Importance of Laughter and Human Interaction
21:23 Leveraging GPT for Problem Solving
22:18 The Downside of Relying on AI
23:45 The Value of Human Interaction in the Workplace
25:09 The Impact of AI on Team Dynamics
27:04 Balancing Efficiency and Human Connection
29:05 The Future of Startups and Human Connection
30:33 The Need for Human-Centric Work Cultures
32:06 Conclusion: Embracing Humanity in the Age of AI