Startup Therapy

Latest Episodes:

Should Startups Be a Family? Jul 28, 2025

Show notes

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the challenges and dynamics of blending friendship and professionalism in startups. They delve into the potential pitfalls of treating your startup team like a family, the consequences on both founders and employees, and the importance of setting clear boundaries. They highlight shared experiences from their early careers and emphasize the need for empathy, respect, and a professional approach to lead effectively without compromising authority.

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:

00:08 The Illusion of Startup as a Family

00:55 Early Career and Peer Dynamics

01:50 The Reality of Founder-Employee Relationships

03:46 The Pitfalls of Treating Employees as Family

05:54 Transparency in Startups: A Double-Edged Sword

07:13 Shared Risk and Misinterpreted Bonds

09:32 The Inevitable Strain on Relationships

12:17 The Limits of Friendship in Startups

16:18 The Evolution of Team Dynamics

18:12 A Throwback to Early Company Culture

18:31 The Impact of a New Hire

19:19 Cultural Misalignment and Realization

20:15 Adjusting Company Culture

21:43 Balancing Professionalism and Empathy

22:50 The Importance of Boundaries

24:18 The Dangers of Forced Inclusivity

28:24 Personal Experiences with Cultural Fit

32:20 The Family vs. Professional Sports Team Metaphor

36:42 Final Thoughts on Company Culture

Can Founders be Replaced by AI? Jul 21, 2025

Show notes

Ryan and Will talk about the growing role of AI in startups. They explore how AI is automating traditional founder tasks like writing, coding, and analyzing data. The conversation delves into the existential threat AI poses to the founder's role and how founders can adapt to this new landscape. They argue that founders should embrace AI to focus on creativity, curation, and leadership rather than being bogged down by routine tasks. The episode underscores the importance of evolving with technology to enhance productivity and innovation, ultimately redefining the founder's job description for the future.

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:
00:34 Can AI Replace Founders?
01:16 The Evolution of AI Capabilities
02:03 AI's Impact on Copywriting and Creativity
03:28 AI in Advertising and Idea Generation
04:44 Embracing AI for Efficiency
06:31 AI as a Force Multiplier
09:44 The Future of AI and Founders
14:36 AI in Coding and Development
17:08 Leveraging AI for Business Growth
19:13 Simulating Business Scenarios with AI
19:38 The Role of AI in Business Decision Making
19:53 The Timeless Nature of Business Challenges
20:48 Embracing AI for Efficiency
21:12 The Unique Human Element in Business
23:40 The Future of Founders in an AI-Driven World
25:50 The Evolution of Founders' Roles
28:05 Leadership and Determination in Business
30:47 The Importance of Vision and Adaptability

What if we run out of goals? Jun 30, 2025

Show notes

In this episode of the Startup Therapy Podcast, Ryan and Will talk about what happens when you hit all your big goals and realize there might not be any more mountains left to climb. They discuss the complex feelings and identity crises that can emerge when success is achieved, and reflect on how to find new meaning and satisfaction beyond traditional goal-setting. The conversation touches on personal anecdotes, the concept of enjoying the process, and how to appreciate the journey in a fulfilling way.

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:
00:27 The Identity Crisis of Achieving Goals
01:05 Personal Reflections on Goal Setting
02:25 The Evolution of Goals Over Time
04:14 The Reality of Achieving Big Goals
07:04 The Trap of Sensationalizing Goals
10:58 The Diminishing Returns of Goal Achievement
19:06 The Two Paths of Goal Setting: Pleasure vs. Pain
20:40 Understanding Pain and Relief
21:42 The Myth of Success Equals Happiness
22:32 Existential Goals and Realizations
23:31 The Challenge of Finding Fulfillment
25:23 Enjoying the Journey vs. The Destination
29:12 Reevaluating Ambitions and Goals
33:11 Building for the Sake of Creation
36:59 Infinite Games and Lifelong Pursuits

Founders, Reinvention IS your Constant! Jun 23, 2025

Show notes

Will and Ryan talk about the fascinating and often overlooked journey of reinventing oneself. Will shares his diverse background, from being an ad guy to becoming a multi-time startup founder, and stresses the importance of embracing various roles to build a comprehensive skill set. The duo emphasizes that becoming a founder isn't a job you get hired for but one you create yourself. They explore how personal and professional reinvention can be the key to success in the startup world, encouraging founders to see themselves as a composite of their varied experiences. The episode is filled with personal anecdotes, practical advice, and an inspiring message: you are not confined to one identity or role — your potential is ever-evolving.

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:
00:43 The Journey to Becoming a Founder
01:28 Reinventing Yourself as a Founder
02:31 The Value of Diverse Experiences
03:55 A Humorous Job List
08:11 The Role of Exposure in Career Choices
13:06 Breaking Free from Career Constraints
19:46 Early Career Hustles
20:22 Learning from Experience
20:53 First Sales Job
21:30 Unexpected Opportunities
23:22 Reinvention Starts Small
24:06 Curiosity and Career Growth
26:14 Building Skills Over Time
28:04 The Power of Starting Small
30:10 Embracing Continuous Learning
32:21 The Value of Diverse Experiences
39:59 Reinventing Yourself as a Founder

Founder Isolation is Getting Worse Jun 16, 2025

Show notes

Ryan and Will talk about the growing isolation that founders are feeling despite having more ways to connect. They delve into how the shift to remote work, the impact of social media, and the rise of AI have contributed to stripping away the humanity from our daily interactions. They share personal experiences and offer insights into why this sense of loneliness has worsened, and most importantly, explore actionable steps founders can take to reconnect, feel less isolated, and build meaningful relationships in an increasingly digital world.

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:
01:05 The Paradox of Connection and Loneliness
02:36 Impact of Remote Work on Founders
16:17 The Role of Social Media in Isolation
20:49 The Distorted Reality of Social Media
21:24 The Cynicism Towards Social Media Posts
22:19 Creating Private Spaces and Personal Connections
23:15 Declaring Relationship Bankruptcy
26:53 The Impact of AI on Authenticity
31:08 The Future of Human Interaction in a Digital World
35:33 Combating Isolation as Founders

Forging Founder Confidence Jun 09, 2025

Show notes

Ryan and Will discuss the journey of becoming a confident founder. Celebrating their 300th episode, they reflect on how learning to lead and building confidence starts with curiosity. They emphasize asking questions, even seemingly silly ones, to gain knowledge and confidence. Will and Ryan also dive into the importance of challenging oneself incrementally and being willing to make mistakes as key steps in growing confidence. They share personal anecdotes and practical advice, making a case for bravery, perseverance, and learning from failures. Perfect for any founder grappling with self-doubt or seeking actionable steps to boost their confidence.

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:
00:58 Building Confidence Through Practice
05:25 The Power of Curiosity
09:25 Asking the Right Questions
14:58 Taking on New Challenges
19:03 Building Confidence Through Small Victories
19:40 Teaching Kids Micro Challenges
20:09 Challenging Yourself Incrementally
21:17 The Line Between Ambition and Recklessness
22:19 Learning Through Incremental Steps
25:37 The Importance of Being Wrong
27:41 Building Confidence as a Founder
31:33 The Role of Bravery in Confidence

Is College a Waste of Time for Founders? Jun 02, 2025

Show notes

In this episode of The Startup Therapy Podcast, Ryan and Will discuss the true value of a college education for aspiring entrepreneurs. They explore whether the traditional path through higher education is the best route for those determined to start their own businesses. With personal anecdotes and economic insights, they argue that college may not always be the ideal path for founders, emphasizing the benefits of real-world experience and early entrepreneurial efforts. They also discuss societal expectations, financial implications, and alternative approaches to gaining the necessary knowledge and skills.

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:
00:17 The Value of a College Degree for Founders
00:55 Challenging the College Norm
01:37 A Real-Life Example: Skipping College for Startups
03:14 Generational Expectations and College
07:25 The Economics of College Education
08:04 The Financial Impact of College vs. Investing
14:19 The Opportunity Cost of College for Founders
20:21 The Power of Compounding Experiences
20:35 Learning at Your Own Pace
20:58 The Irrelevance of Traditional Education
22:19 Founders Need a Broad Skillset
22:57 The Limitations of College
24:33 Alternative Learning Paths
25:57 The Value of Practical Experience
27:44 The Diminishing Value of a College Degree
29:13 Questioning the College Path
33:30 The Founder Mindset
40:18 Restarting the Conversation on Education

Are We Preventing Our Startup From Evolving? May 26, 2025

Show notes

The realities of evolving a startup. Ryan and Will discuss how the first idea is rarely the final solution, sharing insights on how to navigate the pivoting process. Using Uber and their own experiences at startups.com as examples, they explore the dangers of clinging to an initial plan and the importance of staying open to change. They also touch on overcoming ego, internalizing market feedback, and avoiding self-sabotage to ultimately achieve a more successful and fulfilling business.

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 Myth of the Perfect Plan
02:04 The Uber Example: Evolving Business Models
03:55 The Importance of User Feedback
04:48 Facing Investor Expectations
07:44 Ego vs. Agility in Decision Making
08:47 The Afford It Story: Lessons Learned
13:21 Conclusion and Final Thoughts
13:53 The Original Plan and Its Challenges
14:25 Admitting Mistakes and Moving Forward
15:10 Evolving as a Founder
15:58 The Birth of Startups.com
17:26 Learning from Market Feedback
20:45 Detaching Ego from the Product
23:14 The Importance of Adaptation

Building a Startup That Loves You Back May 19, 2025

Show notes

Ryan and Will delve into the complexities of maintaining a healthy relationship with your startup. They discuss their personal experiences and challenges in balancing the demands of a startup with personal well-being. Will shares an incredulous story about a friend enjoying a Tuesday afternoon in the pool, leading to a broader discussion on the importance of setting boundaries and recognizing the signs of burnout. The hosts emphasize the need for self-awareness, prioritizing personal values, and finding joy in the journey, not just the destination. They also touch on the benefits of giving team members autonomy and creating a supportive, non-toxic work culture.

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:
00:32 The Pool Story: A Lesson in Work-Life Balance
02:08 The Toxic Relationship with Work
03:11 Startup Therapy: The Podcast's Origin
08:15 Balancing Work and Family
13:17 Non-Negotiables and Personal Values
14:51 Conclusion and Final Thoughts
15:35 Mitigating Guilt Through Productivity
17:29 The Elusive Goal of Profit
19:21 Emotional ROI in Startups
21:57 Autonomy and Company Culture
24:50 Balancing Safety and Happiness
28:26 Avoiding the Trap of Obligations
29:40 Creating a Non-Abusive Startup Relationship
30:50 Join the Startups.com Community

When Our Friends Resent Our Success May 12, 2025

Show notes

Ryan and Will discuss the surprising reactions founders often face when they achieve success. They explore how unexpected resentment from friends and peers can arise, why it happens, and how to navigate these tricky social waters. Through personal anecdotes and practical advice, they delve into balancing humility and openness about success while staying true to oneself. Tune in to learn about managing relationships as you climb the ladder and handling the inevitable pushback with grace.

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 Unexpected Reactions to Success
02:54 Personal Stories of Resentment
07:57 The Impact of Success on Relationships
12:32 Social Media and Validation
14:01 Processing Success and Insecurities
19:34 Navigating Conversations About Success
21:04 The Validation Loop Dilemma
21:21 Caring About Others' Opinions
21:57 The Spectrum of Self-Presentation
23:17 The Insecurity Behind Social Media Influencers
25:34 The Cost of Flaunting Success
29:04 Extreme Humility and Its Consequences
32:19 Balancing Humility and Pride
37:01 The Art of Humble Bragging
40:39 Avoiding Resentment Through Humility
41:46 The Power and Responsibility of Success
42:38 Join the Startups.com Community

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