Startup Therapy

Latest Episodes:

Is Remote Culture, Actually Culture? Oct 06, 2025

Show notes

Have you ever wondered if remote work is better than being in the office? Ryan and Will dive into their experiences and how their work culture has evolved over 20 years. They discuss the pros and cons of remote work, the importance of autonomy, and how remote setups have stripped away some of the overhead, revealing who truly thrives in this environment. They also explore whether it's possible to create a strong company culture remotely and how the shift has amplified the best and worst in employees. Tune in as they break down their journey from being die-hard office goers to embracing the flexibility and autonomy of remote work.

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:
00:36 The Shift from Office to Remote Work

01:01 Challenges of Remote Work

01:57 Socialization and Remote Work

04:42 Remote Work Rituals and Failures

07:26 Digital Culture and Transactional Work

12:06 Evolving Company Culture

19:14 The Evolution of Workplace Culture

19:34 Starting Fresh: Can We Be Transactional?

20:20 The New Culture: Autonomy and Responsibility

21:37 Balancing Work and Personal Life

23:49 The Value and Challenges of Remote Culture

25:34 Autonomy: The Ultimate Compensation

26:10 Remote Work: Amplifying Strengths and Weaknesses

32:13 The Social Aspect of Work

37:22 The Future of Work: Remote vs. In-Office

Can I Hand Off My Startup? Sep 29, 2025

Show notes

Ever dreamt of handing off your startup to a killer operator and sipping margaritas while the money keeps rolling in? It sounds perfect, but reality often has other plans. In this episode, we break down why passing on the reins isn't as smooth as it seems—from the slow degradation of everyday tasks to the irreplaceable instinct and urgency a founder brings. Discover why certain roles and tasks can be handed off successfully while others, like maintaining culture and strategic vision, often falter without the founder's unique touch. Tune in for practical advice on what you can actually hand off and what you should keep a close eye on to keep your startup thriving.

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:
00:06 The Dream of Handing Off a Startup
00:54 Early Days and Initial Success
02:14 The Startup Dream and Its Challenges
03:47 The Reality of Handing Off a Startup
05:09 The Slow Decline: Signs and Symptoms
07:48 Personal Experiences and Lessons Learned
17:00 The Boiled Frog Syndrome
19:45 The Timeless Nature of Startup Challenges
20:25 The Disconnect Between Perception and Reality
20:53 The Unique Metabolism of Founders
22:06 The Importance of Ownership and Passion
25:01 Handing Off Responsibilities: What Works and What Doesn't
27:43 The Irreplaceable Elements of Leadership
32:58 The Impact of Founder Presence on Company Culture
39:06 The Inherent Urgency of Founders

Did I Just Get Promoted or Fired? Sep 22, 2025

Show notes

Ever wonder what happens when a founder gets 'promoted' out of the CEO role? Ryan and Will dive into the tricky terrain of founder transitions, exploring how it feels to be nudged into roles like Chief Vision Officer or Chairman—positions that often come when a new CEO is brought in. They discuss the emotions involved, the motivations of investors, and the strategies for turning this awkward moment into an opportunity. Whether you're in the thick of this situation or just want to be prepared, this episode provides valuable insights on maintaining dignity, negotiating effectively, and leveraging a graceful exit for future success.

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:
00:24 The Founder Promotion Dilemma
01:07 Personal Experience with Founder Titles
02:26 The Gary Coleman Effect
03:21 The CEO Replacement Backfire
05:29 The Emotional and Financial Impact of Founder Reassignment
10:44 Board Mechanics and Founder Control
13:06 Investor Strategies and Founder Leverage
18:34 Facing the Reality of Founder Reassignment
23:17 Famous Comebacks: Steve Jobs, Howard Schultz, and Jack Dorsey
24:36 The Emotional Toll of Being Replaced
25:10 Turning Emotions into Positive Actions
25:46 Negotiating Your Exit Strategy
30:54 Crafting Your New Role
31:55 The Importance of Maintaining Relationships
37:00 The Worst and Best Case Scenarios

Burnout is a Treatable Injury Sep 15, 2025

Show notes

Ever felt like burnout is inevitable in your startup journey? You're not alone. Burnout can feel like a silent co-founder, but it doesn't have to signal the end of your entrepreneurial story. In this episode, we discuss why burnout happens, how to diagnose it, and most importantly, how to treat it. Discover the importance of pacing yourself, the hidden costs of burnout, and why taking a break is crucial—not just for you, but for your entire team. We'll share personal anecdotes, practical tips, and the value of stepping away to recharge, so you can return stronger and more passionate than ever. Tune in to learn how to recognize the signs of burnout and create a treatment plan that works for you and your startup.

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:
01:01 Personal Burnout Stories
04:46 The Hidden Costs of Burnout
08:41 Recognizing and Addressing Burnout
19:17 Recognizing Emotional Burnout
19:47 Impact of Economic Downturn on Founders
21:19 Personal Struggles and Their Impact on Work
22:13 Diagnosing and Addressing Burnout in Teams
23:04 The Importance of Personal Life in Preventing Burnout
27:32 Strategies for Treating Burnout
29:27 Finding Passion Outside of Work
32:59 Identifying and Mitigating Burnout Triggers
38:25 The Role of Leadership in Managing Burnout

Stop Pretending You Don't Have Enough Time! Sep 10, 2025

Show notes

Ever feel like you need more hours in the day? Turns out, you don't. In this episode, we dive deep into time management for founders, starting with a viral Reddit post that stirred some controversy. We'll explore how compressing your timelines can lead to greater efficiency and free up your schedule for the things that truly matter. Forget the chronic meeting bloat and endless email chains; it's all about optimizing every minute. Discover how focusing on small, incremental tasks can lead to significant progress, both in your professional and personal life. Whether you're a solo founder or leading a team, this episode offers actionable insights to make the most out of your 24 hours.

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:

00:26 The Reddit Experiment: Stirring Controversy
03:53 The Time Compression Revelation
04:32 Analyzing Time Management
07:52 The Cost of Meetings and Conversations
15:21 The Impact of Family on Work Hours
17:44 The Power of Constraints
20:02 The Power of Saying No
20:24 Focus as a Job
20:34 Timeless Solutions
21:06 The Importance of Prioritization
21:34 Efficiency in Communication
22:34 Breaking Down Big Tasks
23:14 Consistency and Compounding
23:25 Building a House with Focus
26:53 Weekly Timelines for Productivity
36:12 Reclaiming Time for Personal Use

Are Founders Aligned with Those Around Them? Sep 02, 2025

Show notes

The complexities of alignment among founders, employees, and even spouses. They debunk the notion that perfect alignment exists, emphasizing that often, perceived alignment is more fiction than reality. The conversation covers the inevitable differences in expectations, contributions, and risk tolerances that arise between co-founders and employees. The hosts also delve into the personal side, exploring how founders' professional decisions impact their relationships at home. Through candid anecdotes and practical insights, they highlight the importance of mutual respect and understanding in managing these fundamentally misaligned expectations in both business and personal life.

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:
00:42 The Myth of Alignment in Startups
01:06 Investor Alignment: Fact or Fiction?
01:48 The Role of Spouses in Startup Alignment
03:09 The Challenge of Aligning with Employees
04:59 Generational Differences in Work-Life Balance
14:50 The Reality of Co-Founder Alignment
21:16 The Challenge of Co-Founder Alignment
22:45 Spousal Support and Startup Life
25:45 Understanding and Managing Differences
28:31 The Myth of Perfect Alignment

Will the Payout be Worth the Sacrifice? Aug 25, 2025

Show notes

The challenging question of whether the sacrifices made in pursuit of entrepreneurial success are ultimately worth the payoff. Will retells his personal story of almost buying an expensive house in Bel Air only to realize, thanks to his wife's intervention, that it wasn't what he truly wanted. The duo explores themes of sacrifice, payoff, and how aligning personal goals with true desires can lead to genuine happiness and fulfillment. Whether it's the freedom to travel or the joy of creating something with your hands, this episode urges founders to carefully contemplate their end goals and ensure their sacrifices lead to meaningful rewards.

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:
00:25 The Beverly Hills House Dilemma
03:05 Reflecting on Sacrifices and Payoffs
06:52 The Decision to Move Back to Ohio
13:42 The Value of Freedom and Purpose
17:46 The Danger of Undefined Goals
22:15 The Illusion of Goals
23:19 Realizing Unwanted Desires
24:13 Shifting Ambitions
26:21 The Fear of Losing Ambition
27:54 Evaluating Sacrifices
33:48 Finding True Fulfillment
36:31 Building a Dream
42:38 Advice for Founders

How Founders Blow Their Fortunes Aug 19, 2025

Show notes

The critical do's and don’ts after a big financial win as a startup founder. They emphasize the importance of not oversharing about your wealth, shifting from an offensive to a defensive mindset, preserving your gains, and being cautious about new investments. They also explore how to handle the psychological and social challenges that come with newfound success, using real-life examples and practical advice to ensure you don't blow your hard-earned money.

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:
00:52 The Myth of the Big Exit
01:52 Emotional and Psychological Impact of Wealth
02:58 The Speech: Congrats, Now Don't Mess It Up
04:23 Financial Management for Newfound Wealth
06:11 The Three Js of Wealth: Judgment, Jealousy, and Jockeying
06:47 The Importance of Keeping Financial Information Private
20:06 The Shift from Offense to Defense in Wealth Management
22:24 The Founder Mentality Shift
23:53 The Casino Analogy
26:45 The Importance of Playing Defense
30:18 The Danger of Proving Yourself Again
36:33 The Save Point Strategy
44:19 The Burn Rate Dilemma
45:24 Conclusion: Preserving Your Wealth

When is Enough, Enough? Aug 11, 2025

Show notes

Ryan and will talks about a critical issue many founders face: knowing when to say 'enough is enough.' They explore the constant pursuit of growth both personally and professionally and how it can turn into a liability if not checked. They dive into the psychological roots of why founders struggle with the concept of 'having enough,' the impact of a scarcity mindset, and the importance of recognizing diminishing returns. The hosts share personal anecdotes and offer practical advice on how to balance ambition with fulfillment, emphasizing the need for diversified 'buckets' of happiness beyond just business success.

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:
00:07 The Founder’s Dilemma: Knowing When Enough is Enough
01:26 The Scarcity Mindset and Its Impact
02:35 The Law of Diminishing Returns
03:12 Personal Anecdotes on Ambition and Satisfaction
05:38 The Concept of Utility in Economics
12:00 Balancing Growth and Happiness in Startups
16:56 Post-Exit: The Risk of Overreaching
20:11 The Downfall of a Legend
21:15 The Cost of Ambition
22:32 The Utility of Wealth
23:25 Chasing More: A Founder’s Dilemma
25:42 The Search for True Happiness
28:48 Redefining Success
33:50 Balancing Ambition and Value

Can Entrepreneurship Alleviate Poverty? Aug 04, 2025

Show notes

How entrepreneurship can transform lives and communities? Will shares his personal journey from a challenging childhood to becoming a successful entrepreneur. They explore whether entrepreneurship can be a means to alleviate poverty, emphasizing the importance of hope, a safety net, and access to education and mentorship. The conversation dives deep into the potential impact of entrepreneurial initiatives on economic development and the need for structured support to foster entrepreneurial success on a global scale.

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:
00:40 The Power of Entrepreneurship to Alleviate Poverty
01:17 Personal Stories of Entrepreneurial Beginnings
02:34 The Ripple Effect of Entrepreneurship
03:38 Teaching Entrepreneurship as a Lifelong Skill
04:46 Hope as the Foundation of Entrepreneurship
05:37 Early Wins and Their Impact
07:17 The Importance of Small Wins
08:20 The Role of Hope and Pride in Entrepreneurship
12:15 The Willingness to Fail
22:49 The Risk of Failure for the Broke
23:45 Historical Context and Immigrant Success Stories
24:46 The Luxury of Credit and Capital
27:03 Entrepreneur Welfare and Venture Capital
29:14 The Case for Minimum Basic Income for Founders
29:40 The Parallel with Education and FAFSA
38:47 The Need for Structured Entrepreneurship Education
39:47 The Role of Hope and Security in Entrepreneurship
45:46 Entrepreneurship as a Solution to Poverty
47:34 Join the Startups.com Community

Our TOPPODCAST Picks

Follow Us

Stay Connected

Related Podcasts

Links

Stay Connected