12 Startup Lessons I learned the hard way (so you don’t have to)

12 Startup Lessons I learned the hard way (so you don’t have to)
September 9, 2025

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12 Startup Lessons I learned the hard way (so you don’t have to)

By Jonathan Joel Mentor | @jonathanjmentor 

I’ve spent the last 15 years in the startup trenches—bootstrapped, VC-backed, B2B, B2C, local, global—you name it. And while I’ve had my wins, the hard lessons really shaped my game. This list? It’s not theory. It’s battle-tested advice for every founder trying to scale smarter, not harder.

 

  1. B2C? Think Twice.  

Consumer apps are alluring but often a gamble. The failure rate is significantly higher compared to B2B ventures. While B2B pays the bills, B2C can break your heart.

 

  1. Don’t Chase VC Before Chasing Revenue.  

Raising venture capital too early shifts focus from satisfying users to seeking media coverage and the next funding round. Impress investors by showing growth and happy customers.

 

  1. Early Hires ≠ Early Wins.  

Startups need doers, not managers. Founders should handle the work until traction is achieved. Hiring too early can lead to minimal output and a lack of innovation.

 

  1. Ignoring SEO? Big Mistake.  

SEO is a long-term investment that builds equity. Relying solely on paid ads can burn through your budget without sustainable results.

 

  1. Content Is King.  

Blogging and content marketing build trust and visibility. Even dedicating an hour a day can yield significant benefits.

 

  1. Social Media Isn’t Optional.

Delaying social media engagement can cost you. Building an audience takes time; start now to reap future benefits.

 

  1. Validate Ideas Early.  

Assuming what your audience wants can lead to failure. Validate ideas quickly to focus on what truly resonates with users.

 

  1. Managers in Startups? Not Yet.  

In the early stages, startups need builders, not managers. Execution is paramount; titles can come later.

 

  1. Don’t Chase Investors—Attract Them.  

Spending excessive time fundraising can detract from product development. Focus on creating value, and investors will come to you.

 

  1. Full-Stack Developers Over Specialized Teams.  

A versatile developer often outperforms a team of specialists in a startup setting. Efficiency and adaptability are key.

 

  1. Hire People You’d Hug.  

Cultural fit matters. If you don’t want to spend time with someone outside of work, think twice before hiring them.

 

  1. Be Cautious with Corporate Partnerships. 

Large corporations may promise big opportunities but can drain resources and shift focus. Ensure partnerships align with your startup’s goals and capacity.

 

Startups are unforgiving. The line between momentum and meltdown is razor-thin. But if this list saves you time, money, or even just one major headache—then it’s doing its job. Learn fast, move smart, and remember: you don’t need to make every mistake yourself to level up. Let mine be your shortcut.

 

These lessons stem from nearly two decades of experience in building startups across various sectors. By sharing them, I hope to guide fellow entrepreneurs navigating the startup landscape.

 

If you wanna see if you’re about to (or currently) f*cking it up, you can use the RevOps Scorecard to course correct and see where your revenue imbalances are coming from.

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Jonathan Joel Mentor is the CEO of Successment and architect of the Provoke Visibility™ campaign, scaling startups and challenging institutions to evolve. UN World Summit Award nominee. www.jonathanjmentor.co

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