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Was Mortgaging My Life Worth it?
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You Only Think You Work Hard
SMALL is the New Big — Embracing Efficiency in the Age of AI
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Never Share Your Net Worth
This is BOOTSTRAPPED — 3 Strategies to Build Your Startup Without Funding
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$10K Per Month isn't Just Revenue — It's Life Support
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If It Makes Money, It Makes Sense
The Hidden Treasure of Failed Startups
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Why Having Zero Experience is a Huge Asset
How About a Startup that Just Makes Money?
How to Recruit a Rockstar Advisor
Risk it All vs Steady Paycheck
A Steady Hand in the Middle of the Storm
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Staying Small While Going Big
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How Startups Actually Get Bought
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Actually, We Have Plenty of Time
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Who am I Really Competing Against?
Investors are NOT on Our Side of the Table
Plan for Bad Times, Budget in Good Times
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Don't Fear the Reaper: AI Edition
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We Can't Stay Out Of The Game For Too Long
What if Our Dreams Are an Illusion?
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Founders, Not All Problems Are Apocalyptic
Stop Listening to Investors
Can You Build a Startup in Less than 40 Hours per Week?
Unlocking the Power of a Startup Community
Strategies to Effectively Raise Capital for Your Startup Business
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What Is an Entrepreneur? A 2023 Guide to Starting Your Own Business
A Guide to Different Stages of Funding for Startups
Time is Our Greatest Asset
The Toll of Everyone Around a Founder
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Once a Founder, Always a Founder
The Invention of the 20-Something-Year-Old Founder
When is Founder Ego Too Much?
Founder Impostor Syndrome Never Goes Away
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The Case Against Full Transparency
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This is Probably Your Last Success
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How to get Customers for Startups
Founder Sacrifice — At What Point Have I Gone Too Far?
The Power of a Growth Mindset: How to Achieve Success in Your Startup
Startup Board Negotiations: How do I tell the board I need a new deal?
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Series A Funding Rounds
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Choosing The Right Type Of Website For Your Business
Startup Failure is just One Chapter in Founder Life
What If my plan for retirement is "never retire"?
Is Quiet Quitting a Problem at Startup Companies?
If a Startup Sinks, Founders Go Down With it
Startup Growth Challenges: The Downfall of Becoming Internally Focused
Analyzing Startup Accounting Results

What Problems DO Just Go Away With Time?

Wil Schroter

What Problems DO Just Go Away With Time?

Every Founder feels like their startup must be the one company that is a total shit show compared to how those other startups must be running.

We believe that if we can just get past this next set of challenges, things will finally be smooth sailing.

What we don't realize, especially if we've never done this before, is that the problems never really go away. It's just a never-ending "whack-a-mole" game with different problems.

Problems Don't Go Away — They Just Change Names

When we're small and scrappy, our problems are all about survival. How are we going to meet payroll? How are we going to land that one early investor?

They feel weighty and life-threatening — and to be fair, they are. But those formative years are stressful in the way high school was stressful.

At the time, we thought if we could just stop getting stuffed into lockers and made fun of at the lunch table, we would be great. But as we got older, those childhood problems just morphed into adulthood problems like finding a spouse and paying a mortgage.

As we grow, our problems will also just change in nature.

Instead of being able to pay our one employee, we're going to be worried about paying 100. Our challenges of having to do "everything ourselves" will transform into not being able to get anything done as an organization.

"Well, What Problems DO Go Away In Time?"

While problems don't go away entirely, our ability to manage them changes. Obviously, with more infrastructure, we can better manage customer issues, product ship dates, and basic infrastructure — like making sure bills are paid on time.

With more revenue, we have more flexibility in how we manage our finances, which means even if we run too lean, we can still make some cuts to get things right again.

So we have more options than we did when it was just two of us in a room sharing a Starbucks.

Growth Actually Creates More Chaos

As the organization grows, so does the complexity. And with it, the chaos.

Every time another person enters the organization, the chaos grows even greater, until one day we look back and think, "Remember how awesome it was when it was just the two us just getting stuff done and not having to worry about all of these people?"

It may be hard to see now, but the problems we're dealing with may be the best problems we've ever had.

In Case You Missed It

What Happens After I've Made It? We always dream about our startups making it big. But what happens when they really do? What happens when all of the risks actually turn into the payouts we had always hoped for? Are we actually happier?

What to Expect in the First Year (podcast). As Founders, we think we know how our products and businesses will look and function for years to come, but as with time, it's nearly impossible to expect the unexpected.

Growth Isn’t Always Good. In many cases, our focus on growth runs counter to what our goals really should be: becoming a better startup — not just a bigger one.

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