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
Is there a line between Founder optimism and delusion? [not-audio_url] [/not-audio_url]

Duration: 37:40
Can founders turn delusion into success? In this episode, Ryan and Will discuss the essential role of optimism in startups. Drawing parallels between founders and firefighters, the duo explores how belief against all odd…
Prioritize Productivity Over Popularity [not-audio_url] [/not-audio_url]

Duration: 31:59
Ever find yourself caught in the trap of confusing visibility with progress? In this episode, we'll delve into why seeking attention can often feel like momentum but doesn't necessarily translate to business traction. Wi…
Better is Better than Bigger [not-audio_url] [/not-audio_url]

Duration: 35:39
Is getting bigger always better for startups? This episode dives into the hidden costs of scaling up and how growth can sometimes make a company worse, not better. Ryan and Will discuss the trade-offs between size and qu…
Founder Authenticity: Use with Caution [not-audio_url] [/not-audio_url]

Duration: 31:17
Ever wonder if being your authentic self at work might sometimes do more harm than good? The delicate balance of authenticity and diplomacy in leadership. From discussing the rare contexts where pure honesty works, to sh…
Founders, Embrace Your Flaws [not-audio_url] [/not-audio_url]

Duration: 41:29
Are you convinced that you need to fix all your flaws as a founder? In this episode, we explore why that's not necessarily true. Ryan and Will dive deep into the idea that both startups and their founders are loaded with…
Can I Hand Off My Startup? [not-audio_url] [/not-audio_url]

Duration: 42:26
Ever dreamt of handing off your startup to a killer operator and sipping margaritas while the money keeps rolling in? It sounds perfect, but reality often has other plans. In this episode, we break down why passing on th…
Did I Just Get Promoted or Fired? [not-audio_url] [/not-audio_url]

Duration: 42:29
Ever wonder what happens when a founder gets 'promoted' out of the CEO role? Ryan and Will dive into the tricky terrain of founder transitions, exploring how it feels to be nudged into roles like Chief Vision Officer or…
Burnout is a Treatable Injury [not-audio_url] [/not-audio_url]

Duration: 39:42
Ever felt like burnout is inevitable in your startup journey? You're not alone. Burnout can feel like a silent co-founder, but it doesn't have to signal the end of your entrepreneurial story. In this episode, we discuss…
Stop Pretending You Don't Have Enough Time! [not-audio_url] [/not-audio_url]

Duration: 40:11
Ever feel like you need more hours in the day? Turns out, you don't. In this episode, we dive deep into time management for founders, starting with a viral Reddit post that stirred some controversy. We'll explore how com…
Are Founders Aligned with Those Around Them? [not-audio_url] [/not-audio_url]

Duration: 40:33
The complexities of alignment among founders, employees, and even spouses. They debunk the notion that perfect alignment exists, emphasizing that often, perceived alignment is more fiction than reality. The conversation…