Real Advice from Entrepreneurs Who Figured It Out the Hard Way

Entrepreneurship is often described as freedom, flexibility, and opportunity.

But if you ask anyone who has actually built something…

They’ll tell you a different story.

One filled with:

• Unexpected challenges
• Hard lessons
• Moments where nothing goes as planned

So I asked a simple question:

👉 What is one piece of advice you would give to aspiring entrepreneurs, based on an unexpected challenge you faced, and how you overcame it?

The responses were powerful.

Different industries. Different journeys.
But the same underlying truth:

💡 The lessons that shape us most are the ones we never saw coming.

1. Resilience Isn’t Optional - It’s the Foundation

Many entrepreneurs shared that the biggest challenge wasn’t external, it was internal.

Staying consistent. Showing up. Continuing even when motivation fades.

As Jamie Maltabes put it:

“Motivation disappears quickly… My confidence in myself was built through action, not the other way around.”

And Jessica Liew reinforced this:

“Setbacks are just signals, not stop signs.”

The lesson:
Success isn’t built on motivation, it’s built on discipline and resilience.

2. Don’t Confuse Activity with Progress

One of the most common traps?

Being busy… but not moving forward.

Glenn Orloff captured this perfectly:

“Don’t mistake ‘activity’ for ‘progress’. Focus on what has become easier for your customers, not how busy you were.”

And Abhinav Gupta highlighted the hidden drain:

“Tiny unresolved issues… together they slow you down.”

The lesson:
Progress comes from clarity and focus, not constant motion.

3. Start Before You’re Ready (Perfection Will Cost You)

Several founders shared a painful realization:

Waiting for “perfect” delays real learning.

Joe Spisak, CEO of Fulfill.com, said it best:

“If you're not a little embarrassed by your first version, you waited too long to launch.”

And Ameet Mehta added:

“Stop building demand. Capture intent that already exists.”

The lesson:
You don’t learn by planning, you learn by doing, launching, and adapting.

4. Adaptability Is the Real Competitive Advantage

Many founders started with one plan… and succeeded with another.

As Matt Goodwin shared:

“Our business took off when we expanded beyond what we originally offered.”

And Kevin Clancy reframed obstacles:

“Don’t try to break through it—turn that obstacle into your competitive advantage.”

The lesson:
Flexibility isn’t optional. It’s often the difference between stagnation and growth.

5. People, Trust, and Relationships Matter More Than You Think

A recurring theme across industries:

👉 Business is human.

Chris Lowe explained:

“Behind every transaction is a person with genuine concerns and emotions.”

And Lewis Hammond added:

“Be a resource and an advocate first; the sales will follow.”

Even hiring came up as a major challenge.

Aleina Almeida shared:

“Hiring the wrong people led to many setbacks… building a dependable team early is crucial.”

The lesson:
Trust, relationships, and people decisions will shape your business more than strategy alone.

6. You Are the Bottleneck (Until You Build Systems)

This one hits hard for many founders.

Olga Kokhan shared:

“The unexpected challenge wasn’t competition—it was realizing how often I was the bottleneck.”

And Dennis Holmes emphasized:

“Responsiveness matters more than scale… speed can determine whether you win or lose opportunities.”

The lesson:
To grow, you must shift from doing everything…
to building systems that scale beyond you.

7. Build the Right Foundations Early

Some of the hardest lessons came from things founders didn’t prioritize early enough.

Kanique Mighty-Nugent shared:

“Not setting up properly from a legal and financial standpoint created long-term challenges.”

And David Batchelor added:

“Fix the pipes before building the house.”

The lesson:
The “boring” foundations—legal, financial, operational—are what make a business sustainable.

8. You Don’t Have to Do It Alone

Another unexpected challenge?

Isolation.

Anthony Warren shared:

“The most unexpected challenge was the isolation… I overcame it by building a network.”

And Steve Schwab emphasized:

“Having a mentor can help you navigate uncertainty with confidence.”

The lesson:
Entrepreneurship isn’t meant to be done alone.

👉 Community is a competitive advantage.

A Shared Truth Across Every Journey

What stood out most wasn’t just the advice.

It was how similar the lessons were, across industries, backgrounds, and experiences.

Different paths. Same patterns.

• Start before you’re ready
• Stay disciplined
• Focus on real progress
• Build relationships
• Adapt quickly
• Don’t do it alone

Join the Conversation

The insights above are just a snapshot.

We received dozens of responses from entrepreneurs and builders, each with their own story, challenge, and lesson.

👇 You can explore their full responses in the comments below.

And if you’re building something of your own:

👉 What’s one lesson you learned the hard way?

✨ Contributors

We’re grateful to the founders, operators, and professionals who shared their insights for this piece, including:

Matt Goodwin, Kanique Mighty-Nugent, Abhinav Gupta, Kuldeep Kundal, Olga Kokhan, Bob Schulte, Essa Al Harthi, Glenn Orloff, Jamie Maltabes, Aleina Almeida, Thomas Danaher, Joyce Tsang, Jessica Liew, Joe Spisak, Guery Cordovadisla, Chris Lowe, Joe Hartman, Erik Daley, Jason Velie, Sergio Aguinaga, Kevin Clancy, Jesse Nguyen, Eric Camardelle, Matthew Slowik, Casey Ryan, Jacob Mullins, Alex Yeh, Steve Schwab, Assaf Sternberg, Damien Baden, Darren Tredgold, Lewis Hammond, Paul Myers, Joel Janson, David Batchelor, Matthew McCourry, Ameet Mehta, Chris Kirshenboim, Chongwei Chen, Eric Turney, Nick Elo, Dennis Holmes, Anthony Warren and others.

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