When Can I Afford to GAMBLE?

When Can I Afford to GAMBLE?

Author: Startups.com January 27, 2025 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 to take risks, how to figure out your "minimum viable risk pool," and why having a financial cushion is key to surviving setbacks.

They share personal stories from their experience at Startups.com, emphasizing the importance of cutting personal and business expenses to stretch your runway and make smarter decisions. This episode is all about helping entrepreneurs understand the financial milestones they need to hit to keep their businesses afloat—and how time plays a big role in navigating risks.

This episode is packed with advice for anyone trying to manage the tricky balance of risk and reward in entrepreneurship. Tune in to learn how to take smarter risks and build a solid foundation for your business!

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:
00:15 Why Taking Risks Is a Luxury

02:08 Balancing Personal and Business Costs

03:44 Lessons from Startups.com

05:55 Why You Need a Risk Buffer

10:25 Figuring Out the Minimum Viable Risk Pool

16:51 Financial Discipline and Budgeting

19:09 The Freedom Fund Explained

26:51 How to Survive Financial Challenges


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
My Competitors Just Raised Funds - Am I Screwed? [not-audio_url] [/not-audio_url]

Duration: 36:25
In today's Startup Therapy Podcast, Wil and Ryan talks about what happens if your competitor got funded. Join as they discuss the common concern of competitors securing funds and share valuable perspectives on why this m…
Can Having Zero Experience Be a Huge Asset? [not-audio_url] [/not-audio_url]

Duration: 33:53
In today's Startup Therapy Podcast, Wil and Ryan explore whether lacking prior experience can be a game-changer for startup founders. Having zero experience means you're new to something, and surprisingly, that can be a…
What If I Build a Startup That Just Makes Money? [not-audio_url] [/not-audio_url]

Duration: 31:19
In today's Startup Therapy Podcast, Wil and Ryan talks about whether a founder should focus on building a startup that just makes money. Ever thought about ditching the whole fundraising craze and simply building a start…
How to Get Rockstar Startup Advisors [not-audio_url] [/not-audio_url]

Duration: 41:07
In today's Startup Therapy Podcast, Wil and Ryan discuss how you can get rockstar advisors for your startup. Discover the common mistakes people make when they are getting people to be their advisors and what are the bes…
Job vs Startup - What Should I Do? [not-audio_url] [/not-audio_url]

Duration: 37:14
In today's Startup Therapy Podcast, Wil and Ryan discuss whether you should get a steady paycheck or start your own startup. Choosing between a regular job and starting your own business is a big decision many face. Work…
Founders Need a Steady Hand in the Storm [not-audio_url] [/not-audio_url]

Duration: 37:39
In today's Startup Therapy Podcast, Wil and Ryan discuss the idea of managing chaos as a founder. Keeping a startup on track is like steering a ship through rough waters. Founders must stay calm and focused amid the chao…
So You Think You Need a Co-Founder? [not-audio_url] [/not-audio_url]

Duration: 34:35
In today's Startup Therapy Podcast, Wil and Ryan discuss the idea of having a co-founder. A co-founder can offer numerous benefits for a business. It allows for shared responsibilities, diverse skill sets, and a support…
Can I Scale My Impact Without Scaling My Team? [not-audio_url] [/not-audio_url]

Duration: 28:09
In today's Startup Therapy Podcast, Wil and Ryan discuss the concept of scaling without adding or hiring more people. Making a significant impact doesn't always mean having a large team. You can achieve remarkable result…
Grind or Guilt, the Founder Dilemma [not-audio_url] [/not-audio_url]

Duration: 43:41
In today's Startup Therapy Podcast, Wil and Ryan discuss about the grind and guilt dilemma of founders. Founders often struggle with the never-ending hard work of growing their business, driven by their passion and ambit…

«1...678910