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When Our Friends Resent Our Success

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When Our Friends Resent Our Success

Startup Therapy Podcast

The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it.

Hosted by

Wil Schroter

Founder + CEO, Startups.com

Wil is a serial Founder having launched 9 companies over 25+ years, 3 being venture funded and 4 having been sold. He generally argues that Founders need to take a much different view of how to build startups.

Ryan Rutan

Founding Partner + CMO, Startups.com

Ryan is a serial founder with 5 companies spanning 3 continents, 20 years and 2 exits. He generally argues with Wil.

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Past Episodes

Episode 295

May 5, 2025

When Our Startup Outgrows Us

Sometimes the most Founder move you can make... is letting go.

Episode 294

April 28, 2025

When Being in the 1% Feels like Failure

Founders are so wired to chase the next milestone that we forget to high-five ourselves for how far we’ve already come. This is a reminder to zoom out and give yourself some damn credit.

Episode 293

April 21, 2025

We Need Outside Interests that Consume Us

If you can’t sit still without spiraling, you’re not broken. You just haven’t found the right non-work challenge to recharge you.

Episode 292

April 14, 2025

If You're Not Terrified, You're Doing it Wrong

Fear’s always in the room when you’re building something that matters. The key is figuring out how to stop avoiding it and start using it as fuel.

Episode 291

April 7, 2025

Make Money First, Then Build a Product

Turns out you don’t need millions in funding to build a real business, just something people will actually pay for.

Episode 289

March 24, 2025

Does LOCATION Matter for Your Startup?

Startup success used to be all about location. Now, it’s about connection, no matter where you are.

Episode 288

March 17, 2025

Are The Sacrifices Worth It?

Startup freedom isn’t free. Let’s talk about the price Founders actually pay.

Episode 282

January 20, 2025

Can Founders Find Contentment?

Contentment or complacency: can entrepreneurs find peace without losing their hustle cred?

Episode 281

January 13, 2025

Why do Investors FIRE Founders?

Ever wondered why investors boot Founders? We’ve got the juicy details and tips on how not to get ghosted out of your own startup.

Episode 280

December 2, 2024

The Burden of Unrealistic Expectations

The only thing faster than startup growth? Founder burnout.

Episode 279

November 25, 2024

How Do I Stay Positive In Tough Times?

If your startup feels like a never-ending dumpster fire, allow us to offer clever ways to keep the flames of productivity burning without roasting your sanity.

Episode 278

November 18, 2024

Are Investors Trying to Push Us Off a Cliff?

Think VCs are just helping startups? Think again — find out why their focus on quick returns could leave Founders stranded.

Episode 277

November 11, 2024

What Previously Funded Founders Do Differently

The road to startup funding is paved with pitfalls — get insider tips to navigate it like a pro.

Episode 276

November 4, 2024

Are Startups Easier for Experienced Founders?

The myth of the "easy second startup" is busted: discover why experience doesn't guarantee success.

Episode 275

October 28, 2024

Who's Working for Who?

The unspoken reality of startup life: why Founders are constantly torn between their vision and the relentless demands of their companies.

Episode 274

October 21, 2024

Let's Get Back to Our Why

Don't let operational hurdles cloud your mission — Discover why staying true to your startup's core mission is key to long-term success.

Episode 274

September 30, 2024

Does Startup Success Validate Us Personally?

No matter how much success we create with our startups, it almost never "cures" our need for validation. If anything, it often makes it worse.

Episode 273

October 14, 2024

How We Secretly Lose Control of Our Startups

As Founders, we're so worried about losing control of our startups to investors that we completely overlook how we secretly lose control to everyone else.

Episode 272

September 16, 2024

Should Kids Follow in our Founder Footsteps?

Do we want our kids to follow the same path as us? Or should we just provide the tools and support to foster independent choices rather than push entrepreneurship?

Episode 271

September 9, 2024

The Evolution of Entry Level Workers

There's an evolving landscape of entry-level hiring for startups. With AI on the rise and global talent a click away, building efficient teams under tight budgets is a true balancing act.

Episode 270

September 2, 2024

Assume Everyone Will Leave in Year One

Employee turnover (whether untoward or amicable) is inevitable in the startup world.

Episode 269

August 26, 2024

Was Mortgaging My Life Worth it?

Want to avoid a future riddled with regret? (of course you do!) You'll need these specific goals and timelines.

Episode 268

August 19, 2024

What's My Startup Worth in an Acquisition?

Many startup Founders have unrealistic expectations when it comes to selling their business — yes, this means you probably do, too.

Episode 267

August 12, 2024

Is My Ambition My Enemy?

Ambition, while necessary for building innovative companies, can become more detrimental than beneficial — but where's the tipping point?

Episode 266

August 5, 2024

Are Startups in a "Silent Recession"?

Despite economic indicators suggesting otherwise, many startup Founders are struggling with reduced capital flow and stagnating customer acquisition.

Episode 265

July 29, 2024

Do Founders Deserve Their Profit?

First of all, success should be celebrated not vilified. So why do Founders get the short end of the stick when it comes to earning what they've worked so hard for?

Episode 264

July 22, 2024

The Utter STUPIDITY of "Risking it All"

There's a huge gamble in the 'bet it all' startup mentality.

Episode 263

July 15, 2024

Why Most Founders Don't Get Rich

There are many common struggles of making money in the startup world. Join us to explore what those are and what to do about it.

Episode 262

July 15, 2024

Investors will be Obsolete, The End of Venture Capital

These two details might reshape the future of funding in the startup ecosystem as we know it.

Episode 261

July 1, 2024

Why is a Founder so HARD to replace?

Removing a Founder often leads to failure for a startup. Some could say they're irreplaceable — and they'd be right!

Episode 260

June 24, 2024

We Can't Grow by Saying "No"

Here's a secret: startups thrive by committing to new challenges, even if the path isn't immediately clear.

Episode 257

June 17, 2024

This is WHY More Money Means MORE Problems

There's a BIG misconception that reaching revenue milestones in startups will solve all problems. In reality, each milestone brings new challenges.

Episode 256

June 10, 2024

Committees Are Where Progress Goes to Die

Founders should avoid relying on committees for critical decisions. Consider yourself warned. And here's why.

Episode 255

June 3, 2024

Giving Up Equity? Press Pause First

The most expensive decisions we will ever make as a Founder all come at the beginning — when we are most vulnerable.

Episode 254

May 27, 2024

Why Do 99% of Founders Suck at Asking for Help?

Tune in for tips on how to develop the muscle for asking the right questions — Founders do not need to reinvent the wheel with all the untapped wealth of knowledge available.

Episode 253

May 20, 2024

The Value of Actually Getting Paid (Avoid This Big Danger)

If we don't make money, it doesn't make sense. See the importance of paying yourself regularly, even when building a high-potential startup.

Episode 252

May 13, 2024

Will Investors Bail Me Out? Brutal Truth About Startup Investments

Founders commonly believe that future investments will pay back their financial commitments. When in reality, the chances of getting 'paid back' stem from other outcomes completely.

Episode 251

May 6, 2024

Is the Problem the Player or the Coach?

Should we be constantly evaluating our team's performance? Short answer: YES. Tune in to discover why, and learn how to take actionable steps toward building a higher-quality team.

Episode 250

April 29, 2024

Do People Really Want Me to Succeed?

Let's explore the harsh reality of seeking support as a Founder. Surprisingly, a limited number of people genuinely want to see a founder succeed. And this is the reason why.

Episode 249

April 22, 2024

You Only THINK You Work HARD — The Hard Work Illusion

There's a common misconception about 'working hard' within startups. Let's challenge the notion of what constitutes 'hard work' and the danger of equating all effort with success.

Episode 248

April 15, 2024

SMALL is the New Big — Embracing Efficiency in the Age of AI

Is AI the startup Founder's dream come true? Short answer: absolutely. Let us explain...

Episode 247

March 18, 2024

This is BOOTSTRAPPED — 3 Strategies to Build Your Startup Without Funding

In a world fixated on funding, could the real path to startup growth lie in resourcefulness and astute expense management?

Episode 246

March 11, 2024

The Spectrum of Investor Advice

There are many dangers of acting on investor feedback without considering its relevance, potential bias, and the investor's qualifications. Let's discuss the importance of understanding the context and motivation behind their advice.

Episode 245

March 4, 2024

$10K Per Month isn't Just Revenue — It's Life Support

Earning at least $10,000 per month is one of the most important milestones in your startup career. Here's why.

Episode 244

February 26, 2024

Why Do VCs Keep Giving "failed" Founders Money?

Maybe investing in Founders who have shown they can bounce back and learn from failure can ultimately change how we think about startup success — tune in to find out why.

Episode 243

January 27, 2025

When Can I Afford to GAMBLE?

Risk is a luxury disguised as hustle. The less runway you have, the smarter your bets need to be.

Episode 243

February 19, 2024

If It Makes Money, It Makes Sense

Generating revenue and being willing to do whatever it takes to move a startup forward is essential for startup success. But how do we overcome challenges in achieving financial sustainability?

Episode 242

February 12, 2024

The Hidden Treasure of Failed Startups

Let's talk about the hidden treasure of failed startups and uncover the secrets of success amidst startup wreckage.

Episode 241

February 5, 2024

My Competitors Just Raised Funds — Am I Screwed?

What's the most common concern of competitors securing funds? Tune in for valuable perspectives on why this might not be a cause for panic.

Episode 240

January 29, 2024

Can Having Zero Experience Be a Huge Asset?

Having zero experience means you're new to something, and surprisingly, that can be a good thing. But for startup Founders, could a lack of experience help you succeed or fail?

Episode 239

January 22, 2024

What If I Build a Startup That Just Makes Money?

Ever thought about ditching the whole fundraising craze and simply building a startup that puts money in your pocket? It's not just about surviving in the business jungle, it's about thriving on YOUR terms.

Episode 238

January 15, 2024

How to Get Rockstar Startup Advisors

Navigating the advisor landscape is like treading a fine line between wisdom and well-intentioned faux pas. Let's decipher whether your startup needs an advisor's touch or if all you need is some solid advice.

Episode 237

January 8, 2024

Job vs Startup — What Should I Do?

Choosing between a regular job and starting your own business is a life-changing decision. Let's unpack the realities behind each choice to weigh out what is best for YOU.

Episode 236

December 4, 2023

Founders Need a Steady Hand in the Storm

Founders must stay calm and focused amid the chaos, juggling priorities and tackling problems as they arise. Ultimately, a Founder's ability to handle the daily whirlwind defines their success in the unpredictable world of entrepreneurship.

Episode 235

November 20, 2023

So You Think You Need a Co-Founder?

A co-founder can offer numerous benefits to a business. However, finding the right co-founder whose values align with yours and who complements your strengths and weaknesses is crucial for a successful partnership.

Episode 234

November 13, 2023

Can I Scale My Impact Without Scaling My Team?

Making a significant impact doesn't always mean having a large team. Let's delve into the strategies that empower a small team to make a substantial difference, proving that size isn't the only measure of success.

Episode 233

November 6, 2023

Grind or Guilt, the Founder Dilemma

How can we achieve a harmonious equilibrium that allows us to pursue our entrepreneurial dreams while also nurturing our mental and physical health and maintaining meaningful relationships?

Episode 232

October 30, 2023

Are Founders Driven by Fear or Greed?

What really drives Founders? Is it the fear of failure, or is it the pursuit of wealth and success (often labeled as greed)?

Episode 231

October 23, 2023

What if I'm Building the Wrong Product?

Have you ever had an idea, but you're just not sure if it's good? Welcome to the club. How does any entrepreneur know if they’re building the right product?

Episode 230

October 16, 2023

How Startups Actually Get Bought

It's easy to get confused about how much a startup is really worth, and people sometimes have high hopes that don't match reality. To succeed in this startup world, it's important to understand these details and be realistic about what to expect.

Episode 229

October 9, 2023

Am I Quitting My Startup, Or Letting Go?

Quitting isn't always a failure. Sometimes it's a strategic move toward a brighter entrepreneurial future.

Episode 228

October 9, 2023

How long do we ACTUALLY have?

It's easy to get sidetracked by short-term goals and immediate survival mode. But here's the deal: it's not about chasing quick wins; it's about building something that stands the test of time.

Episode 227

September 25, 2023

Can I Replace Myself as a Founder?

Founders struggle to step aside in a company because their deep commitment and personal connection to the company's mission are hard to duplicate. So, can Founders ever replace themselves?

Episode 226

September 18, 2023

Who am I Really Competing Against?

Founders are often never satisfied because they constantly set new, self-imposed benchmarks and goals. Is it possible to find a balance between ambition and recognizing achievements?

Episode 225

September 11, 2023

Investors are NOT on Our Side of the Table

In the startup world, it's important to recognize that investors and Founders don't always see eye to eye (big surprise there). Good communication and finding common ground are key to ensuring the startup's success in the long run.

Episode 224

September 4, 2023

Plan for Bad Times — Budget in Good Times

It's not all sunshine during the good times, and not all doom and gloom during the bad times. It's about striking that perfect balance in your startup's strategy. So, what's the secret to achieving longevity in the ever-shifting landscape of entrepreneurship? Tune in the find out.

Episode 223

August 28, 2023

When a $40M is More Than a $200M Exit

Let’s delve into the maze of startup exits, exploring the delicate interplay between exit values, ownership, and the real-world implications.

Episode 222

August 21, 2023

Don't Fear the Reaper (AI Edition)

Founders shouldn't fear changes in technology because embracing advancements can bring various advantages, ultimately fostering growth and success.

Episode 221

August 14, 2023

Don't Let Investors Become Your Customers

When you prioritize investor demands over customer needs in pursuit of additional funding, you risk eroding customer trust and loyalty, negatively impacting your long-term business sustainability.

Episode 220

August 7, 2023

We Can't Stay Out Of The Game For Too Long

Startup Founders can't afford lengthy breaks from the game because the skills and mindset crucial for entrepreneurship can weaken over time. Here's why.

Episode 219

July 31, 2023

What if Our Dreams Are an Illusion?

Sometimes, the startup journey is more important than the final outcome, so it's crucial to think about whether the sacrifices are really worth it for your long-term happiness and sense of purpose.

Episode 218

July 24, 2023

What if this isn't a "Big Business"?

By reevaluating goals and priorities, Founders may discover the benefits of a steady and enduring approach that aligns with their vision and values, which can be mountains better than just "scaling rapidly" with no direction.

Episode 217

July 17, 2023

Founders, Not All Problems Are Apocalyptic

While running a startup can be challenging and bring various obstacles, not every problem leads to failure or signifies the end. Tune in to hear how Founders can view problems as opportunities for growth and improvement.

Episode 216

July 3, 2023

Stop Listening to Investors

While investors can provide valuable insights and expertise, Founders should exercise caution when relying too heavily on their advice. Here's why.

Episode 215

June 26, 2023

Can You Build a Startup in Less Than 40 Hours a Week?

Building a startup typically requires a significant investment of time and effort. While it's theoretically possible to work on a startup for less than 40 hours a week, it may significantly impact the chances of success.

Episode 214

June 19, 2023

Are Bootstrapped Startups Less Valuable Than Venture-Funded Startups?

The value of a startup isn't only determined by its funding source. It depends on things like its potential in the market, how much it's growing, how well its product fits the market, and the skills of its team, etc. — regardless of how it's funded.

Episode 213

June 12, 2023

Why Founders Don't Ask For Help

Founders sometimes hold back from asking for help because they worry about losing control, looking weak, burdening others, or feeling like they have to do everything themselves. However, it's actually really important for founders to push past these concerns and ask for help. Here's why.

Episode 212

June 5, 2023

Can I Design My Startup Around My Life?

By carefully planning, testing things out, and being open to adjustments, you can create a startup that fits seamlessly into your personal life instead of consuming it. It's all about finding that sweet spot where work and life complement each other.

Episode 211

May 29, 2023

Founders, Time is Your Greatest Asset

In the fast-paced world of startups, thinking long-term is a total game-changer. It not only toughens you up, but it also attracts investors and partners who are in it for the long run, boosting your chances of scoring lasting success in the crazy world of startups.

Episode 210

May 22, 2023

The Toll on Everyone Around a Founder

Being a Founder can take a toll on everyone around you in different ways. Let’s deep dive into the nitty-gritty of how it impacts family, friends, and relationships.

Episode 209

May 15, 2023

Big Starts Breed False Victories

There's a big problem with early praise and big hypes at the beginning of a startup, with no assurance of success. Let's discuss why early praise can be a double-edged sword for any budding entrepreneur.

Episode 208

May 8, 2023

Once a Founder, Always a Founder

Being a Founder is an integral part of our identity, and setbacks with one startup shouldn't make us doubt our ability to succeed in the role. After all, being a Founder isn't just a job – it's a deeply ingrained part of our DNA.

Episode 207

May 1, 2023

The Invention of the 20-Something-Year-Old Founder

With the changing landscape of technology and business, more young people are starting successful companies. Let's discuss the opportunities available to young people today, and how starting a business has evolved over the years.

Episode 206

April 24, 2023

When is Founder Ego Too Much?

We all know that confidence is key when you're starting a business, but sometimes it can be hard to tell when that confidence has turned into full-on arrogance. So how do we avoid this trap?

Episode 205

April 17, 2023

Founder Imposter Syndrome Never Goes Away

Imposter syndrome can be tough, whether you're a seasoned startup pro or just starting out. But with the right mindset and tools, you can learn to recognize and overcome those nagging self-doubts.

Episode 204

April 3, 2023

Always Take Money Off The Table

Let's discuss how Founders often miss out on paying themselves and why it's essential to grab it when it happens. You might not get this chance again — seize the moment and take that money off the table now.

Episode 203

March 27, 2023

Should I Feel Guilty For Failing?

While it's perfectly natural to feel disappointed when a startup fails, it's not cool to let guilt eat away at you. The key is to bounce back from setbacks and keep pushing forward, no matter how tough things get.

Episode 202

March 20, 2023

The Case Against Full Transparency

Being honest with your customers and clients will help attract more people to your company, but excessive sharing of information could also create some problems. So, how much transparency is too much?

Episode 201

March 13, 2023

Does My Startup Really Need Full Time Employees?

Let’s find out what full-time employment realistically is for a startup and how you make the most out of it.

Episode 200

March 6, 2023

This is Probably Your Last Success

You’re there, you finally made it — so you think you can replicate that success? The truth is: the probability is low, so what can you do to change this mindset?

Episode 200

March 6, 2023

This is Probably Your Last Success

You’re there, you finally made it — so you think you can replicate that success? The probability of remaking that success is probably low and you can’t base your future success on something that you’ve done before, so what can you do to change this mindset?

Episode 199

February 20, 2023

How Many Times Can My Startup Die?

Starting a business is just a series of recovering from deaths — but when does it start getting better and when would you realize that you should stop?

Episode 198

February 13, 2023

How Should I Share My Wealth with Family?

If you're always one call away from your family or friends whenever they need money and it’s supposed to be a “loan” but they have yet to pay anything back — Tune in to find out how you can actually build a financial relationship with your family!

Episode 197

February 6, 2023

Why Do VC Funded Startups Love "Fake Growth?"

Some Startup companies may look like they are soaring and scaling really fast but in reality, these Startups are spending more than they are getting back from revenue. So how can we identify whether we are going the real growth route or the fake growth route?

Episode 196

January 30, 2023

Founder Legends Are Less Fun When You Are Living Them

Whenever we hear a story of somebody else’s win most likely we find it inspiring and decide that we want to be like them someday. But are you really willing to go through the pain they had to live through just to be where they are now?

Episode 195

January 23, 2023

Can Middle Schoolers be Founders?

There are tons of benefits when you teach young children about entrepreneurship. Not only do you raise children with better critical thinking skills, but you’ll also raise problem solvers.

Episode 194

January 16, 2023

Founders, At What Point Have We Sacrificed Too Much?

You might think now that the return on investment of all the time you spent working instead of doing the things you will never get back will be worth it in the long run but think again — are you willing to pay that price?

Episode 193

January 9, 2023

Founders, How to Tell the Board "I Need a New Deal"

If you’re a Founder and your company is earning a lot of money but you can’t even touch the profit – then maybe it’s time to have that conversation with the board. But how can you do this without being turned down?

Episode 192

December 12, 2022

Founders, Failure is Just One Chapter in Life

Stop thinking that failure is forever. Your whole life is a book with different chapters and each has its own challenges. Once you finish a "bad" chapter, started on the next one, because failure is just one chapter in your life.