Startup Therapy

Latest Episodes:

When Our Startup Outgrows Us May 10, 2025

Show notes

In this episode of the Startup Therapy Podcast,Ryan and Will delve into the emotional journey of startup founders who feel out of place in the very companies they built from scratch. They discuss the guilt and struggle founders experience when their roles change and they no longer enjoy their jobs. They share personal anecdotes and examine the impact of forced roles, from management misfits to a loss of personal fulfillment. The duo also explores the concept of evolving with or beyond your startup, and how to come to terms with these difficult but often necessary transitions.

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:
00:48 The Shift from Building to Managing

01:29 The Struggles of Management

02:13 The Evolution of Roles

04:17 The Peter Principle in Action

05:29 The Emotional Toll of Management

08:34 Reflecting on the Past and Moving Forward

09:57 The Realization and Acceptance

12:39 The Dilemma of Founder Evolution

13:10 Learning from the Past

13:42 Commitment and Introspection

15:02 The Cost of Doing What You Hate

17:40 Recognizing and Embracing Change

20:16 The Hard Decision to Move On

25:03 Celebrating Growth and Moving Forward

When Being in the 1% Feels like Failure Apr 28, 2025

Show notes

Ryan and Will discuss the psychological challenges founders face by constantly looking ahead and rarely celebrating their achievements. They explore how important it is for founders to practice gratitude and recognize their progress, even if their ultimate goals haven't been reached. The conversation delves into personal experiences, including Ryan's move to Guatemala and Will's time in Beverly Hills, highlighting how perspective and gratitude can significantly impact one’s satisfaction and motivation in their entrepreneurial journey.

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:
00:29 The Psychological Cost of Milestones
00:58 The 1% of Startups
02:01 Celebrating Small Wins
02:38 The Comparison Trap
03:45 Balancing Credit and Complacency
04:33 Contrasting Success Stories
09:14 Perspective on Startup Success
16:26 The Olympic Mindset and Startup Mentality
17:39 The Power of Perspective and Gratitude
19:35 Balancing Ambition and Gratitude
21:16 Family Traditions and Simple Joys
22:47 Reinforcing Self-Worth and Capability
28:19 The Curse of the Exited Founder
31:02 Changing Perspectives for Greater Happiness

We Need Outside Interests that Consume Us Apr 21, 2025

Show notes

Dive into the common struggle founders face with burnout and the inability to truly relax. Ryan and Will share their personal experiences and discuss how traditional relaxation methods often fail for them. Instead, they highlight the importance of finding other meaningful and challenging obsessions outside of work to channel their energy. From woodworking and home-building to martial arts, they explore how these activities can provide a sense of accomplishment, progression, and actual mental rest, ultimately making them better and more effective in their startup journeys. Tune in to gain insights on how to recharge as a founder by embracing big, consuming projects that challenge and fulfill you.

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:

00:44 The Struggle with Relaxation
01:36 Failed Attempts at Relaxation
03:32 Vacation Dilemmas
05:52 The Need for Mental Engagement
09:47 The Importance of Completion
14:07 Finding New Problems to Solve
22:10 Woodworking as a Solution
24:13 The Obsession Begins: From Birdhouses to Building a House
24:48 The Challenge of Building a House from Scratch
25:35 Balancing Work and Passion Projects
26:31 The Importance of Completion and Physical Activity
27:53 Managing Overwhelm and Finding Solutions
29:14 The Power of Small, Consistent Efforts
30:22 The Role of Meaningful Side Projects
33:17 The Need for Mental and Physical Challenges
36:21 The Value of Overwhelming Projects

You probably should be TERRIFIED. At least a bit.. Apr 14, 2025

Show notes

Ryan and Will discuss the prevalent fear in the market due to economic uncertainty in April 2025. They delve into how fear is a constant companion for founders and argue that it's not a weakness but a strength. Drawing on personal experiences, including public speaking and risky business moves, they illustrate how leaning into fear can drive massive growth and success. Comfortable activities rarely lead to significant achievements, they argue, emphasizing that true progress requires embracing discomfort. They also highlight the importance of conditioning oneself to fear and rejecting complacency to ensure continuous growth and impactful outcomes.

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:
00:35 Founders' Relationship with Fear
01:35 Fear as a Motivator and Asset
02:38 Personal Experiences with Fear and Risk
03:17 Balancing Risk and Reward in Decision Making
06:36 The Role of Fear in Entrepreneurship
07:05 Cultural Differences in Risk Perception
12:57 Embracing Fear as Part of the Job
14:55 Building Resilience Through Failure
15:39 Embracing Fear in Business
16:02 The Role of Fear in Motivation
17:46 The Danger of Complacency
19:25 Taking Big Risks for Big Rewards
21:23 Balancing Fear and Progress
25:44 Facing Public Speaking Fears
30:08 The Importance of Leaning Into Fear

Make Money First - Then Make a Product Apr 07, 2025

Show notes

In this episode, Ryan and Will discuss the common misconception that startups need funding before generating revenue. They emphasize that the actual business isn't just the product but the revenue it generates. The discussion covers various strategies to bootstrap and generate cash flow, including building a minimal viable product, offering related services, and even taking on side gigs or unconventional methods to bring in money. By doing so, startups can extend their runway and better validate their business model before seeking significant investment. The episode includes examples from famous startups like Zappos and Airbnb to illustrate these points.

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:|
00:51 The Broken Assumption About Funding
01:29 Generating Revenue Before the Product
02:39 Examples of Early Revenue Generation
03:07 The Zappos Story: Validating Demand
08:06 Personal Anecdotes on Testing Demand
10:27 The Importance of a Minimum Viable Product
18:39 Service-Based Proxies for Products
21:21 The Unexpected Success of Pitch Deck Services
22:04 Assumptions About Entrepreneurs and Investors
23:48 The Role of Services in Startup Success
25:33 The Importance of Revenue and Profitability
28:53 Creative Ways to Fund Your Startup
34:10 The Value of Bootstrapping and Hustle

It's really HARD to REPEAT A WIN Mar 31, 2025

Show notes

Will and Ryan discuss the dangerous mindset founders can fall into after hitting it big with their startups. They reflect on the story of Peter Chesky, co-founder of Wish, who became a billionaire during the tech IPO boom of early 2021 but saw his net worth plummet as the company's stock tanked. The episode emphasizes the importance of treating any major payout as if it's the last one you'll ever receive. With only a small percentage of startups ever having significant exits, and even fewer doing it repeatedly, Ryan and Will stress why founders should be cautious with their newfound wealth instead of assuming it will keep flowing.

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 The Rise and Fall of Wish
03:01 Lessons from the Wish IPO
05:15 The Psychology of Founders
11:52 A Counter Story: Priceline's IPO
15:13 Reflecting on High School Memories
15:37 The Illusion of Endless Wealth
15:51 The Reality of Financial Downturns
19:09 Understanding Venture Capital Statistics
21:28 The Rarity of Repeat Success
24:18 Advice for Founders: Secure Your Wins
28:11 The Importance of Financial Safety
30:39 Final Thoughts: Keep the Win

Does LOCATION matter for your startup? Mar 24, 2025

Show notes

Ryan and Will discuss the evolution of startup location strategies. They reminisce about the bygone era when relocating to major hubs like San Francisco was essential for success due to access to talent, investors, and networking opportunities. Now, with advancements in remote work, AI, and digital connectivity, these factors have become less relevant. Ryan and Will delve into the changing dynamics of raising capital, building teams, and cultivating networks without needing to uproot one's life to a specific city.

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:

00:39 The Shift in Startup Location Importance

01:46 Reevaluating the Need to Move for Startups

01:58 The Impact of Remote Work and COVID-19

03:51 Debating the Necessity of Moving to San Francisco

06:12 Talent Acquisition in the Remote Work Era

09:23 Financial Considerations and Cost of Living

15:10 The Role of Investors in the New Startup Landscape

17:54 Questioning the Need for Large Engineering Teams

18:21 Capital Requirements and Investor Expectations

19:14 The Evolution of Pre-Seed Rounds

22:27 The Impact of Technology on Investment

23:43 Relocating for Networking Opportunities

27:13 The Shift in Startup Location Necessities

32:03 The Value of Flexibility in Startup Locations

35:59 Conclusion: Startups Can Thrive Anywhere

Are The Sacrifices Worth It? Mar 17, 2025

Show notes

In this episode of the Startup Therapy Podcast, the guys tackle the big question: was the entrepreneurial journey worth it? They discuss the sacrifices, the missed experiences, and the immense pressures that come with being a founder. Will shares a touching story about his daughter's unprompted appreciation for his hard work, leading to a reflection on whether the grinding was worth the outcome. Both hosts also highlight the freedom, flexibility, and the unique sense of achievement they've gained. However, they caution about the inevitable costs and the importance of balancing life and startup aspirations. A must-listen for anyone questioning the value of their entrepreneurial path.

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:

00:49 A Moment of Gratitude

02:42 Was It All Worth It?

06:02 Missed Experiences and College Life

11:00 The Weight of Responsibility

15:12 Habits and Hardships

19:32 Guilt and Work-Life Balance

24:20 The Timeless Nature of Startup Challenges

24:52 The Hidden Costs of Success

25:47 The Value of Sacrifice

26:39 The True Meaning of Freedom

28:04 The Journey to Personal Agency

29:20 The Impact of Entrepreneurship

31:15 The Irony of Wealth and Freedom

35:12 The Cost of Corporate Success

45:44 Balancing Life and Startup

Are Founders Forged Over Youth? Mar 11, 2025

Show notes

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter discuss how childhood experiences influence the entrepreneurial journey. They explore why many founders' origin stories trace back to their early years and how formative events can plant the seeds of entrepreneurship. Will shares his personal story of selling candy as a child, highlighting moments that taught him vital business skills. The conversation also delves into the importance of agency, the tools needed for entrepreneurial success, and the role of parents in nurturing a child's potential to create their own path.

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:

00:13 Exploring Founder Origin Stories
01:51 Will's Childhood Story
10:14 The Power of Agency
10:53 Teaching Kids About Agency
20:54 Personal Reflections on Agency
21:22 The Power of Agency and Optimism
22:14 Parental Protection vs. Empowerment
22:40 Real-Life Stories of Overcoming Adversity
24:40 The Magic of Agency in Hardship
26:42 Tools for Founders and Kids
27:23 Early Lessons in Entrepreneurship
34:56 The Importance of Sales Skills
42:29 Teaching Kids the Value of Agency
43:22 Join the Startups.com Community

Assets OVER Exits Mar 03, 2025

Show notes

In this episode of Startup Therapy, Ryan Rutan and Will Schroeter challenge the startup world's focus on big exits and venture capital. They highlight the benefits of cash-flowing businesses, showing how consistent profits can lead to financial security. Using real examples, they explain how making $10K a month can be as powerful as having millions in the bank—emphasizing sustainable growth and long-term 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:
00:19 The Value of Consistent Cash Flow

01:23 Examples of Profitable Local Businesses

03:37 The Misconception of Startup Exits

03:49 Real-Life Stories of Successful Small Businesses

06:16 The Broken Narrative of Startup Wealth

07:26 Reevaluating Business Success Metrics

09:05 The True Value of a Profitable Business

09:38 Calculating the Financial Impact

13:20 The Reality of Business Exits

18:09 Replacement Value vs. Exit Value

19:14 The Value of Experience and Pre-existing Solutions