In this episode Ryan and Will delve into the intense pressures faced by founders from investors, peers, and the startup community. They discuss how these external expectations often drive founders to pursue goals misaligned with their personal beliefs and values. The conversation explores how unchecked expectations can lead to burnout and misguided efforts. They share insights on the importance of auditing and resetting personal and business expectations to ensure they align with one's true goals and values. The hosts also highlight the dangers of comparing oneself to other founders or industry giants, and emphasize the significance of building a business that meets personal fulfillment rather than external benchmarks.

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Resources:
Startup Therapy Podcast 
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn 
 
 / startups-co  

Join our Network of Top Founders 
Wil Schroter
 
 / wilschroter  
Ryan Rutan
 
 / ryan-rutan  

What to listen for:
00:32 The Source of Pressure and Expectations
03:32 Investor Expectations and Their Impact
04:05 Personal Story: Missing Investor Expectations
05:44 The Reality of Investor Expectations
10:15 Comparing Yourself to Other Founders
17:45 The Peer Comparison Trap
18:06 Personal Journey: From Poverty to Success
20:01 The Futility of Social Media Comparisons
23:07 Tying Success to Self-Worth
28:20 The Illusion of Goals and Success
31:53 Reevaluating Startup Expectations
36:43 Conclusion: Building What Matters to You

Ryan and Will discuss the omnipresent challenges that come with running a startup. They delve into the perpetual 'shit storm' that founders face and share practical advice on how to keep moving forward even when everything feels like it's falling apart. Key points include regaining perspective, converting anxiety into actionable tasks, breaking down large goals into manageable micro-goals, and finding healthy obsessions to channel stress. They emphasize the importance of maintaining a positive outlook, not just for personal sanity but for the wellbeing of the entire team, and share personal anecdotes and strategies that have helped them through their toughest times.

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Resources:
Startup Therapy Podcast 
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn 
 
 / startups-co  

Join our Network of Top Founders 
Wil Schroter
 
 / wilschroter  
Ryan Rutan
 
 / ryan-rutan  

What to listen for:
00:07 The Perpetual Shit Storm of Startups
01:01 Practical Advice for Founders in Crisis
02:10 Regaining Perspective During Tough Times
05:08 Personal Stories of Overcoming Challenges
15:29 The Importance of Taking Action
20:41 Managing Anxiety with Side Tasks
21:58 The Power of Micro Goals
23:37 Breaking Down Big Tasks
26:29 The Importance of Focus
32:07 Finding Healthy Obsessions
41:08 Building Momentum with Small Wins
43:14 Join the Startups.com Community

In this episode of the Startup Therapy Podcast, Ryan and Will delve into the often misunderstood motivations of venture capitalists. They discuss why investors push startups to grow rapidly, the pressures VCs face to deliver returns within a specific timeframe, and the fundamental differences between the stakes for founders and investors. The episode uncovers the reasons behind the 'push you off a cliff' approach, the impact of the 2 and 20 model on VC behavior, and the importance of understanding these dynamics to better navigate the startup journey.

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https://www.startups.com/newsletter

Resources:
Startup Therapy Podcast 
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn 
 
 / startups-co  

Join our Network of Top Founders 
Wil Schroter
 
 / wilschroter  
Ryan Rutan
 
 / ryan-rutan  

What to listen for:
00:11 Understanding Investor Motivations
01:12 The VC Time Crunch
03:57 Profit vs. Growth: A VC Perspective
13:25 The Reality of VC Salaries
16:29 Founders vs. Investors: Different Stakes
19:00 Conclusion: Aligning Goals with Investors

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the daunting realities of raising capital for startups. By sharing insights and experiences from both first-time and repeat founders, they delve into the recurring theme of regret found amongst entrepreneurs who've gone through the funding process. Topics include the hidden costs of raising money, the pitfalls of losing focus, and the challenges of working with investors. The hosts offer practical advice on when to raise funds, how to mitigate the risks of distraction, and the importance of being selective and strategic about bringing investors on board. Whether you're gearing up for your first round of fundraising or re-evaluating your approach, this episode provides valuable lessons to help navigate the complex landscape of startup financing.

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https://www.startups.com/newsletter

Resources:
Startup Therapy Podcast 
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn 
 
 / startups-co  

Join our Network of Top Founders 
Wil Schroter
 
 / wilschroter  
Ryan Rutan
 
 / ryan-rutan  

What to listen for:
00:14 The Reality of Raising Funds
00:38 Founders' Regrets and Reflections
02:15 The Perils of Not Getting Paid
04:22 Understanding Founder Compensation
11:04 Strategies for Better Compensation
13:24 Challenges with Profitable Companies
15:02 The Pressure to Grow or Bust
15:16 The Dilemma of Raising Too Early
15:47 The Vulnerability of Early Stages
16:22 The Importance of Timing in Fundraising
16:56 The Pitfalls of Early Funding
17:28 The Distraction of Fundraising
20:34 The Impact of Investor Expectations
28:23 The Challenge of Having a New Boss
31:50 Key Takeaways and Final Thoughts

In this episode of the Startup Therapy Podcast, Ryan and Will debunk the myth that each startup venture becomes progressively easier with experience. They explore the truths and fallacies surrounding repeat entrepreneurship, sharing personal anecdotes and insights from their extensive history of building and acquiring startups. Discussing expectation management, the double-edged sword of experience, and the harsh realities of repeating past mistakes, Ryan and Will emphasize that while experience offers certain advantages, it does not guarantee success in new ventures. They also highlight the emotional resilience required to endure the cyclical nature of startup challenges and the ever-present difficulties of achieving product-market fit and successful marketing, regardless of prior victories.

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https://www.startups.com/newsletter

Resources:
Startup Therapy Podcast 
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn 
 
 / startups-co  

Join our Network of Top Founders 
Wil Schroter
 
 / wilschroter  
Ryan Rutan
 
 / ryan-rutan  

What to listen for:
00:15 Debunking the Myth of Easier Startups
01:27 The Double-Edged Sword of Experience
02:32 Drawing from Multiple Experience Buckets
05:15 Expectation Management in Startups
09:39 Avoiding Duplicate Mistakes
13:01 Raising Capital: Lessons Learned
15:16 The Value of Experience in Decision Making
17:07 The Reality of Investor Promises
17:17 Understanding People: A Founder's Key Skill
18:38 Emotional Maturity in Leadership
20:00 Challenges That Never Get Easier
21:57 The Ever-Changing Landscape of Product Market Fit
25:39 Marketing Struggles for Experienced Founders
27:40 The Pain of Failure: It Never Gets Easier
31:30 The Value of Experience and the Role of Luck
32:38 Join the Startups.com Community

Ryan Rutan and Will Schroter explore the intricate and often misunderstood relationship between founders and their startups. They tackle the question of whether the founder works for the startup or vice versa, challenging common perceptions shaped by societal views and political discourse. The hosts discuss the unspoken 'contract' entrepreneurs form with themselves, the inevitable trade-offs of startup leadership, and the sacrifices founders make for their companies. They emphasize the emotional and financial tolls on founders, the discrepancies in founder-employee dynamics, and the need for startups to stay aligned with the founder's original mission. This episode stresses the importance of maintaining control and balancing personal goals with the demands of the startup ecosystem.

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https://www.startups.com/newsletter

Resources:
Startup Therapy Podcast 
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn 
 
 / startups-co  

Join our Network of Top Founders 
Wil Schroter
 
 / wilschroter  
Ryan Rutan
 
 / ryan-rutan  

What to listen for
00:35 The Founder vs. Startup Dilemma
00:51 Political and Economic Perspectives
01:40 The Reality of Founders' Lives
03:00 The Initial Contract of Founders
05:11 The Shift in Founders' Roles
06:15 The Permanent Struggle of Founders
07:43 Revisiting the Founders' Goals
10:34 The Reality Check
15:30 The Investor's Impact
15:44 The New Boss: Investors and Liabilities
16:49 The Pain of Payroll: Sacrificing Founder Salaries
19:10 Credit Cards and Cash Flow: Desperate Measures
21:20 The Founder’s Dilemma: Sacrifice and Equity
23:42 The Reality of Startup Success: Rare and Elusive
28:28 The Emotional Toll: Identity and Relationships
31:49 Conclusion: Building a Startup That Works for You

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter explore the vital importance of maintaining a startup's foundational 'why' – the core reason for its existence. They discuss the excitement and clarity that founders experience in the early stages, the operational challenges that can cause them to lose sight of their mission over time, and practical strategies for rekindling that original passion. Through personal anecdotes and examples of companies like Apple and Google, the hosts underscore how minor compromises can erode a company's core mission. They emphasize the need for founders to continuously revisit and reinforce their original motivations to ensure sustained passion and purpose. Listeners will gain insights on recognizing when they've deviated from their vision, the benefits of realigning with the 'why', and actionable steps to recenter their focus, all while maintaining clarity and engagement within their teams.

Sign up for the Startups Newsletter
https://www.startups.com/newsletter

Resources:
Startup Therapy Podcast 
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn 
 
 / startups-co  

Join our Network of Top Founders 
Wil Schroter
 
 / wilschroter  
Ryan Rutan
 
 / ryan-rutan  

What to listen for
00:29 The Importance of 'Why' in Startups
03:17 Losing Sight of the 'Why'
05:24 Diagnosing the Loss of 'Why'
09:21 The Impact of Compromises
15:56 Tiny Compromises Lead to Major Changes
18:48 The Slippery Slope of Compromises
19:50 Losing Sight of the 'Why'
20:50 Rediscovering the Purpose
22:12 The Importance of Remembering the 'Why'
24:30 Practical Steps to Reconnect with the 'Why'
30:55 Identifying and Correcting Misalignments
35:36 The Constant Battle to Maintain the 'Why'

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the complex dynamics of maintaining control in a startup. They explore the misconception that not having investors means maintaining control and highlight the various ways founders inadvertently lose control—from customers, co-founders to their own staff. They delve into the idea that control is a currency spent for growth and emphasize the importance of understanding and strategically managing the areas founders are willing or unwilling to cede control over. They reveal how seemingly routine decisions can lead to significant shifts in control, urging startup founders to be proactive in understanding and negotiating these exchanges.

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https://www.startups.com/newsletter

Resources:
Startup Therapy Podcast
https://www.startups.com/community/st...
Website
https://www.startups.com/begin
LinkedIn
  / startups-co 

Join our Network of Top Founders
Wil Schroter
  / wilschroter 
Ryan Rutan
 

In this episode of the Startup Therapy Podcast, Ryan and Will explore the complexities of encouraging their children to become entrepreneurs. With nearly 300 episodes discussing the founder's journey, they delve into whether they'd want their kids to follow the same path. They recount personal experiences, weigh the pros and cons, and discuss the importance of allowing their children to make their own decisions. The episode emphasizes providing the tools and support to foster independent choices rather than directing them towards entrepreneurship.

Sign up for the Startups Newsletter
https://www.startups.com/newsletter

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: The Founder’s Dilemma
00:55 A Proud Yet Conflicted Parent
02:27 The Value of Experience
05:03 Balancing Passion and Practicality
08:10 Nurture vs. Nature in Entrepreneurship
09:59 The Role of Education and Constraints
16:21 The Reality of Entrepreneurship
18:56 Reflecting on Founders' Struggles
19:39 Balancing Optimism and Realism in Entrepreneurship
19:59 The Timeless Nature of Startup Challenges
21:31 Empathy and the Reality of Startup Therapy
23:10 The Impact of Parental Influence on Career Choices
25:23 Encouraging Authenticity in Children's Career Paths
30:12 Empowering Kids to Make Their Own Decisions
35:07 Final Thoughts on Raising Future Founders

In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Will Schroter discuss the evolving landscape of entry-level hiring for startups. They dive into why U.S. college graduates have fallen to the fourth pick for entry-level positions, overtaken by AI, global talent, and experienced young professionals who leverage new tools and platforms to gain relevant skills. They explore the benefits of each hiring option, debunk common misconceptions about global talent, and outline how these changes empower startups to make smarter, more economical hiring decisions. The discussion offers valuable insights for startup founders navigating the challenges of building efficient teams under tight budgets.

Sign up for the Startups Newsletter
https://www.startups.com/newsletter

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: The Changing Landscape of Entry-Level Talent
01:26 The Rise of AI in Startups
03:48 Global Talent: A New Frontier
07:30 Young and Hungry: The New Entry-Level
10:19 Challenges and Opportunities for College Grads
15:57 Resource Allocation in Startups
24:06 Stop Guessing and Get the Answers
24:16 The Global Talent Pool Advantage
25:15 Quality Concerns and Misconceptions
27:21 Parallel Validation in Startups
32:51 The Rise of Young and Hungry Talent
35:51 Evolving Job Market Expectations
39:50 The Changing Landscape of Hiring
45:20 Conclusion: Embrace the New Opportunities

In this episode of the Startup Therapy Podcast, Ryan and Will discuss the challenges of managing early-stage startup teams, particularly the high likelihood of turnover and the risks of handing out equity prematurely. They talk about the emotional toll of losing key team members and offer practical advice on creating vesting schedules and setting realistic expectations to safeguard against these common pitfalls. The conversation also touches on the dynamics of initial hires, the importance of flexibility, and the need to balance passion with practical considerations in team building.

Sign up for the Startups Newsletter
https://www.startups.com/newsletter

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 to Startup Challenges
00:09 The Reality of Early Startup Teams
01:25 Startup Weekend Insights
02:38 The First Love Analogy
03:44 The Commitment Dilemma
04:24 Life Happens: Unplanned Disruptions
12:02 The Fragility of Equity-Based Compensation
13:45 Long-Term Team Dynamics
15:32 Understanding the Nature of Turnover
17:44 The Emotional Impact of Employee Departure
18:52 The Reality of Passion and Commitment
27:20 Equity Distribution and Vesting Schedules
31:50 Preparing for Inevitable Change