6 Lessons From Startup Founders They Learned The Hard Way

There’s no real way of knowing what it’s like to launch and run a startup without ever having it done it. You can read every book on the market and listen to every podcast and still every bit of imposter syndrome in the world. You can also have the most detailed plans and still feel like you got hit by a freight train.

Having some of the right information right from the start, however, can make a world of difference in early success. And some of that information can come from things real startup founders have learned along the way on the same path you’re planning to take or are underway with now.

So we reached out to founders in our network, and we asked them about real lessons from startup founders that they wish they had known when they first started out. Let’s take a look at what they had to say. 

1. Don’t Fall for Shiny Object Syndrome 

A lot of startup founders begin their venture with a really, really great idea. Too often, too many end up abandoning that great idea or straying from it because they come up with new, other exciting ideas along the way.

“Remember that focus is the ultimate force multiplier,” said Eric Siu, founder of the digital marketing agency Single Grain and established SaaS entrepreneur. “Too many founders, including myself, get shiny object syndrome. If you can combine focus with thinking in decades, you will be unstoppable.”  

So don’t get distracted— stick to your great idea unless the data is telling you that you’re stuck in a sunk cost fallacy loop, and try to not get too distracted by the shiny new ideas and objects in your periphery until it’s time. 

2. Know How to Sell Change to Your Customers 

Every time Facebook changes their interface, users complain for weeks, and when Netflix first changed its prices, I thought people would riot if they could. Consumers typically don’t love change, and knowing how to navigate this is crucial since no startup will stay stagnate. 

That’s the lesson that Brad Smith of Codeless and Wordable learned the hard way. 

“Customers do not like change. No matter how much you’re improving the UI/UX, introducing new features, or streamlining a process inside your app so people can find things faster & easier, existing customers will initially resist it because it’s different than what they’re used to. 

“So plan for that in advance by providing lots of preemptive updates about what’s changing, allow some time for people to still use the old version before forcing them to switch, and provide better education (whether through blog posts, video, or in-app messaging) to help them understand why these changes are better for them in the long run. You can’t and won’t win everyone over. But you will cut down on the self-inflicted headaches you give yourself.”

3. Audience is Everything 

Understanding your audience is crucial for everything startups do. It will shape product development, marketing, sales efforts, and your lead nurturing efforts. 

That’s the hard-won lesson that Dave Shanley from Content Camel had to share.   

“Audience is everything. 

“For startup founders – don’t get confused by marketing jargon, what your VC partner advises, or think that customer discovery is enough. When you’re building a product from the ground up, the first principle metric is your audience size. If you begin with thinking about how to attract and retain an audience, that is literally the foundation of any traction for your product and for your company. 

“After starting 4 companies, selling 2 startups, and advising other founders on go to market – audience size is the defining characteristic of success. By focusing on audience growth – it gives you permission to start now (with your email newsletter, your research, offering value, refining your ideal customer profile, nailing your messaging) and not waiting for product signups to be the sole endpoint for your audience. Hang in there, and the founders with the biggest audiences win.

“The “audience” totally gets lost in most efforts. VCs and PE don’t even get it. I advised a company that had an amazing product, but it wasn’t until they hired a dev with 40k Twitter followers that it really clicked.”  

4. Never Stop Investing in Your Sales Pipeline 

Lead nurturing is a process. Anyone who has ever worked in marketing or sales can tell you that, but it’s still something that startup founders sometimes forget. And if you do forget it, you can be in a world of financial hurt. 

 “Sales cures everything in a company,” said DJ Vallauri, founder and president of Lodging Interactive. “If you have a consistent pipeline of prospects and are closing profitable deals, you’ll have the financial resources to handle any obstacle that is sure to come up. Investing energy and resources into your entire sales pipeline is crucial, and on top of that, it’s important to keep a close eye on determining how to attract and convert high-value or high-retaining clients that will keep the sales coming in.”  

5. Determine How to Test Effectively Early 

Every resource online and in text will tell you that testing is vital for the success of most startups. Testing will only help you get the results you want, however, if you’re testing effectively, especially since it can cost thousands and thousands of dollars.

This is the lesson shared by Cassy Aite, CEO of Hoppier. 

“One lesson we learned the hard way was how to generate demand for our products and services. We have spent millions of dollars on testing channels that just didn’t have any results (from ad networks to sponsoring events and everything in between). We thought we were testing but in reality, we had no real strategy.  

“Eventually, we learned how to test different demand generation channels the right way. As a result, our customer acquisition costs are 1/10th of what they used to be. This means we can grow much more efficiently and need much less investment to grow fast!”

 6. Underestimating The Market 

It’s easy to think when you launch a great, inventive, and much-needed product that your target audience will be falling all over themselves to become users. Unfortunately, that’s just not how it works; momentum in the market is essential, and if you want to really disrupt an industry, it takes work.  

“An early mistake that I learned the hard way was thinking the best product always wins. Maybe I took Field of Dreams to heart but I secretly hoped that “if I build it, they will come,” explained Ajay Pondicherry, CEO of Curb Hero. 

“So I completely underestimated how much time and effort it’d take to get real estate agents to even consider trying Curb Hero.  We knew the product was better than anything else out there but would constantly see other solutions recommended by influential people in the business! It was really painful and I actually became cynical about the industry…but then got serious about marketing and getting our existing users to advocate for Curb Hero‘s value. That boosted the general awareness and also motivated more real estate agents to give us a try.”

Final Thoughts 

Every startup is unique, and every founder will have their own unique, bizarre, frustrating, and thrilling journey. It can be an enormous amount of hard work, but it’s also wildly rewarding. Knowing a few essential lessons upfront can help you stay focused and avoid a few expensive and time-consuming mistakes that can derail your progress.

These six lessons are a great place to start. 

What do you think? What lessons have you learned the hard way? Which stood out out to you most? Share your thoughts in the comments!