Is Remote Culture, Actually Culture?

Is Remote Culture, Actually Culture?

Author: Startups.com October 6, 2025 Duration: 38:39

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


Building a company is far more chaotic and personal than any business school case study lets on. Startup Therapy from Startups.com digs into that reality, moving past polished success stories to focus on the raw, unvarnished journey. Hosts Wil Schroter and Ryan Rutan, who have each navigated these trenches themselves, lead conversations that feel more like essential conversations between founders than a standard interview show. They tackle the specific pressures that come with trying to transform an idea into something meaningful-the financial strain, the team dynamics, the personal sacrifices, and the frequent moments of doubt that rarely make the keynote speech. This podcast operates on a simple premise: the best guidance comes from those who have been there, not from abstract theory. Each episode is a candid session, dissecting the professional hurdles and the intense emotional toll that founders manage daily. You’ll hear direct talk about fundraising fails, partnership conflicts, burnout, and the small victories that keep everything moving forward. It’s a resource for anyone in the thick of building something, offering practical perspectives and a sense of shared experience when the path gets especially tough. The dialogue is straightforward and focused on actionable insight, providing a genuine look at the resilience required to change the world, one startup at a time.
Author: Language: English Episodes: 100

Startup Therapy
Podcast Episodes
Does LOCATION matter for your startup? [not-audio_url] [/not-audio_url]

Duration: 36:57
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 n…
Are The Sacrifices Worth It? [not-audio_url] [/not-audio_url]

Duration: 47:45
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 be…
Are Founders Forged Over Youth? [not-audio_url] [/not-audio_url]

Duration: 43:45
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 ear…
Assets OVER Exits [not-audio_url] [/not-audio_url]

Duration: 39:42
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 profi…
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Duration: 32:58
In this episode of the Startup Therapy podcast, Ryan and Will chat about how startup success isn’t always a straight path. They use Mark Cuban’s story as a prime example, showing why sticking it out for the long run is s…
What Would I do Differently [not-audio_url] [/not-audio_url]

Duration: 33:18
In this episode of The Startup Therapy, Ryan Rutan and Will Schroter explore the 'what if' scenarios that often preoccupy founders. Will shares personal milestones, showing how taking bigger risks shaped his journey. The…
When Can I Afford to GAMBLE? [not-audio_url] [/not-audio_url]

Duration: 30:41
In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroter dive into an interesting perspective: taking risks in entrepreneurship is actually a luxury, not the norm. They break down what it really costs…
Can Founders Find Contentment? [not-audio_url] [/not-audio_url]

Duration: 43:19
In this episode of the Startup Therapy Podcast, Ryan Rutan and Will Schroeter delve into the anxiety surrounding contentment in the startup ecosystem. They question the conventional wisdom that equates contentment with s…
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Duration: 45:48
Ryan Rutan and Will Schroeter discuss the complexities and challenges faced by startup founders, particularly the frequent occurrence of founders being replaced by investors. The conversation delves into the motivations…
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Duration: 38:00
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 misalig…