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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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.

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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
00:29 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

In this episode of the Startup Therapy Podcast, hosts Ryan Rutan and Will Schroter delve into the sacrifices that come with building startup companies. They explore the dangerous ambiguity of not having specific goals and timelines, using personal anecdotes to illustrate the costly trade-offs. Will reflects on his milestone birthday and the realization that 'later' never seems to arrive, sparking a discussion about the true worth of deferred happiness and success. The conversation underscores the importance of quantifying goals and ensuring that sacrifices made today lead to genuinely rewarding outcomes. They emphasize that the journey must be carefully balanced with immediate gratification to avoid a future riddled with regret. Through vivid storytelling, they highlight the crucial lessons for founders on how to navigate the complex landscape of ambition, sacrifice, and personal fulfillment.

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

00:21 The Danger of Vague Goals

00:57 Personal Reflections on Sacrifice

02:16 Quantifying Sacrifices and Rewards

04:03 The Reality of Sacrifice

05:27 Anecdotes of Sacrifice

15:08 The Moment of Truth

18:04 The Grand Experiment in Beverly Hills

18:36 The Struggles of Finding a Home in LA

19:07 Realizing the Cost of Living in Bel Air

20:34 Questioning the Move: A Moment of Clarity

23:10 The Decision to Return to Columbus

23:21 Reflecting on Sacrifices and Rewards

25:42 The Founder's Paradox: Happiness vs. Sacrifice

28:31 The Reality of Achieving Success

35:27 Balancing Sacrifice and Returns

In this episode of the Startup Therapy Podcast, Ryan Rutan and Startups.com founder Will Schroter discuss the unrealistic expectations that many startup founders have when it comes to selling their business. They detail the common pitfalls and misconceptions about startup valuation, the differences between raising capital and selling, the realities of private equity, and the dangers of deferred compensation. With insights from their own experiences of buying and selling companies, Ryan and Will provide a candid look at how to navigate the tricky world of startup acquisitions and set more realistic expectations for exit strategies.

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 Acquisitions

00:16 Realistic Expectations in Business Sales

01:09 Understanding the Acquisition Process

01:37 Our Acquisition Experience

02:29 Challenges in Closing Deals

04:31 The Importance of Direct Communication

07:08 The White Knight Fallacy

13:07 Investor Expectations vs. Reality

20:35 The Figma Acquisition: A Case Study

21:12 Understanding Market Leadership and Valuation

21:44 The Reality of Acquisition Multiples

24:53 The Spectrum of Potential Buyers

26:07 Private Equity: The Predatory Buyer

28:32 The Harsh Truths of Selling a Startup

32:53 Cash vs. Deferred Compensation

39:15 Managing Expectations in Startup Exits

In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter discuss the often overlooked costs of ambition in the startup world. They explore how ambition, while necessary for building innovative companies, can become a debilitating force, leading to severe health issues, strained relationships, and emotional burnout. Using personal anecdotes and analogies, they emphasize the importance of recognizing the tipping point where ambition becomes more detrimental than beneficial, and advocate for a balanced approach to sustain long-term personal and professional health.

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 Ambition in the Startup World
00:30 The Double-Edged Sword of Ambition
01:27 The Escalating Costs of Ambition
02:18 Ambition's Impact on Founders' Lives
05:22 Personal Stories of Ambition and Sacrifice
12:52 The Cultural Reward of Sacrifice
16:16 Understanding Technical Debt and Burnout
16:58 The Hidden Costs of Ambition
17:06 Financial Struggles and Early Warning Signs
18:20 Impact on Relationships
20:40 Mental Well-being and Isolation
23:55 The Ultimate Price: Physical Health
27:12 A Rational Perspective on Work-Life Balance
28:46 Final Thoughts and Advice