32 Valuable Startup Lessons From Successful Entrepreneurs - .TECH
startup lessons

32 Valuable Startup Lessons From Successful Entrepreneurs

Building a successful name for your startup is not a function of ‘by chance’. It takes a lot of discomfort, uneasiness, and creativity to start with an idea and build it every day. Every entrepreneur’s journey is riddled with startup lessons unique to their struggles and challenges.

Learning how to run a business and learning to be an entrepreneur has taught several business owners valuable lessons. Such is the journey of an entrepreneur’s life. We asked 32 successful entrepreneurs and business strategists to share their startup lessons and stories of struggle, learning, and success. This post will help you learn from successful entrepreneurs and gain evergreen insights when it comes to growing a startup.

We hope this will inspire you as you build your own sweet story of building a tech startup!
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32 Lessons from Successful Entrepreneurs

1. Anything is possible if you persevere. 

Don’t give up. Take the plunge and persist. The prerequisite is having something you’re passionate about to get you through the dark times – that mission is what will sustain you.

You should be excited and motivated to go to work every morning and feel like you made a difference in someone’s life at the end of the day. Once you have those feelings, that job will become more than a job – it will be your passion and your career.

In addition, be ready for anything: plan for scale, have the right team!

Startup lesson by Sara Schaer, co-founder and CEO of Kango

2. Find the right problem and solution.

You will make money on this problem if you find a perfect solution and sell it to the right people. If the idea behind your business is not bringing any value to people, it won’t last long.

Entrepreneurship means to live a life of daily motivation. People’s feedback about your product should bring you energy to bring more meaning to everything that you create.

Sometimes, you’ll regret the choices you have made because they didn’t prove to be right, but you should be willing to learn the lessons those decisions taught you.

Networking and meeting new people, mentors, and advisors crucial as these people can validate your business idea. Sometimes their advice is wise; sometimes it’s not. Learn how to filter everything you hear and keep only what you think is appropriate.

Lesson from entrepreneur Alex Shumaiev, CEO & Co-founder at CruiseBe.

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3. Learn four vital values and skills.

You must possess these skills to be a good entrepreneur:

  1. Patience: Only patience and your endurance will help you to get along your tough periods to welcome the good times.
  2. Improvisation: Sometimes you will face a sudden blockade when your automation is at full speed. You have to quickly perceive the deviation of the situation and take instant decisions to get hold of the situation.
  3. Confidence: Sometimes you will fall in uncomfortable situations and quitting might seem the right option. Your self-confidence will rescue you in those times.
  4. Loyalty: Whatever your business is, it won’t last long unless you remain truly loyal to your customers and employees.

Startup lesson by Andrei Vasilescu, CEO and Digital Marketing expert of DontPayFull

4. It’s all about people.

Team building is one of the most important things for any organization. It is an opportunity to build trust, strength, and reinforce culture. A common misconception about team building is that it’s meaningless or that it’s an empty exercise, which is far from the truth. Simple events such a potluck also go a long way, so team building events need not be extravagant.

Lesson by entrepreneur Marcus Harjani, Co-Founder at FameMoose .

5. Ask crucial questions before you start.

Too many startups overestimate how much demand there will be for their product or service. Even though you may love it, not everyone is going to like chocolate-covered olives. So the most important questions to ask are:

  • How large is your potential market?
  • Who are your competitors and do they have similar products or services?
  • What part of their business model can you improve upon?

Ask your friends and family for their opinions, run surveys and conduct focus group meetings to generate some authentic opinions on how well-received your product or service will be.

Startup learning shared by Kristin Marquet, founder and managing director of Creative Development Agency.

6. Get ready to be alone and lose friends.

While immediate family and close friends will always be supportive by sharing on social media, writing reviews, actually using your product, bringing food to the office at midnight, etc.

But, second-tier friends such as your bar buddies, ex-colleagues, and college mates, may not understand the work it takes to build something from scratch.

They can’t fathom why you won’t be able to grab a Happy Hour or dinner on a Tuesday.  Slowly, but surely, these friends will quit asking and become mere acquaintances.  Over the span of 4 years, many of my friendships have turned out this way.

Not that I would change anything but I wish I had known how much of strain being an entrepreneur would have on personal relationships.

Entrepreneurial lesson by Gene Caballero is the  Co-Founder of GreenPal


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7. Think about lifetime service delivery to customers.

If you’re going to create a solution, you should be able to deliver it for the next 10 years. That’s the only way to generate ongoing cash flow.

Don’t ask one customer to pay $500,000 but ask 500,000 customers to pay $1.00. If all customers contribute on a regular basis, you will grow your business for sure. I almost went broke not following this advice.

Another biggest change I made was to hire people to do everything for me so that I have time to think. Starting up doesn’t always mean you have to do it all alone.

Team related learning by entrepreneur Walt Bayliss, owner of Universal Media Online

8.  Build your business around the life you want to have.

Make time for your family, for leisure, and for self-care. It’s easy to get caught up in the challenges of running a business. It is important to make your business a priority, especially at the beginning.

But it’s also easy to fall into the habit of making it your only priority. And if your business structure is so dependent on you for the day to day operations, it’ll be difficult to carve time out for yourself.

Startup lesson by John Jonas is the Founder at OnlineJobs.PH 

9. Work on constant product iterations. 

Don’t attempt to achieve the end vision on the day of your startup launch. Think evolution rather than revolution.

In our early days, we made the mistake of believing that we knew what the final platform would look like, the features that would be required, and the entire user journey.

The result was a lot of wasted time, complex development projects that suffered from frequent delays and releases that were riddled with bugs.

We now work on a product iteration basis, always having a vision of where we’d like to take the product, but taking a step-by-step approach that allows us to constantly adjust and pivot where required based on customer feedback and sales statistics. I’d always recommend this approach to others.

Entrepreneurial lesson by Charles Cridland, co-founder of YourParkingSpace.co.uk

10. Cover all the bases across your co-founders.

In technology, you need to build a thing that is hard to build, and you need to sell a thing that is hard to sell because it’s new. A lot of founding teams have some of these skill sets but not all of them.

Don’t forget that you can always bring on a 3rd founder. Covering all the bases greatly increases your chances of being successful. After you lock in the core team, making your first few hires is also quite critical.

Another advice for tech founders is solving a problem that people are willing to pay for. Charge your very first customers to make sure they are willing to pay.

A good line to use when your prospective customers push back on paying you goes something like this, “I’d love to get you on-board here, and as an early adopter, you’re paying 1/10th what people are going to be paying in a year, because we’re going to be doing so much more so much better.

And your price will be locked in now. Also, you get to have a hand in shaping the direction of the product to solve your exact problems first.” That makes it feel a lot more reasonable for your prospects to buy early.

Startup learning by Steven Benson, Founder and CEO of Badger Maps


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11. Create an internal timeline of milestones but don’t judge yourself on that.

You’re just going to be wrong and way off base because there are so many things that you cannot account at the beginning.  This is critical to know because we always judge our progress against these timelines.

Going in with that understanding will keep you motivated and prevent you from quitting or getting down on yourself. Multiply your timeline by two in order to give yourself a range to work within.

This is especially critical for student entrepreneurs because their entire lives are predicated on judging their progress against timelines-semesters.  Setting a foundation for a business doesn’t work that way.  It requires a different mindset; getting an A in class vs. trying to win at life by building something unique to you.

Entrepreneurial lesson by Ravi Ramkeesoon, founder of FindMyFans

12. Be prepared to eat glass. 

Technology is difficult. New innovations disrupt the old at light speed. When I started off, there was just the web now we have mobile web, smartphone apps, VR-AR, crypto, the blockchain, AI and the list goes on.

If you aspire to be a tech entrepreneur, make sure that you are passionate about technology & engineering. Do not give excuses that you don’t understand tech stuff and that you will hire some tech resource to solve your problems. You should know the foundation of each and every technology out there and its relevance to your business.

Lesson by tech startup founder, Dibu Paul, owner of of Alchetron

13. Business is 80% sales.

Sales are the best indicator that your business is striking a chord with customers and meeting a real need (that they’re prepared to pay for). (Like you), I’m the type of entrepreneur who would prefer to spend my time designing and building new products and features. However, it takes an incredible amount of hustle to pitch and explain your business, convince your target market to try it and eventually decide to purchase.

This means that the most important role of an entrepreneur is to talk to customers – on the phone, in person, and via email or messaging platforms. Be prepared to spend the vast majority of your time in sales-mode. In one of my previous businesses, we tried to employ experienced salespeople and at one point we even attempted to outsource the sales function.

It wasn’t until I embraced sales myself and spent a large portion of each day making sales calls that we really understood what was going through customers’ minds and what needed to change.

Sales are really the ultimate feedback from the market and the sooner you can get this feedback, the sooner you can make changes to your business, product or message to get that elusive ‘product-market fit’. Take it from me, if you can’t make sales, something needs to change!

Tech startup lesson by Fiona Adler who writes about entrepreneurship at DoTheThings.com and is the founder of Actioned.com 

14. Nurture your professional network.

Whenever I am introduced to someone in-person or by email, I always connect with them on LinkedIn.

It is important to begin to develop your modern Rolodex while you are in college, or when you start your first job.  You never know when you need an introduction to a person or company that some acquaintance can provide.

Through proactively maintaining my LinkedIn network for a decade, I have over 5,000 connections working at every major company and industry.  It is rare that I need an introduction to someone that we do not have a mutual connection with, and I have used this network to meet investors, business partners, and future employees.

Startup lesson by Symon Perriman, FanWide’s President and Founder


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15. A tech start-up’s journey is similar to white water rafting.

You know where you want to go and the rapidly changing river is full of obstacles to circumvent in order to reach your destination. However, you have to design and test a new raft that is currently only a concept and drawing on a whiteboard.

You have to define how your raft is different and what benefits it will offer to potential customers. Next, you build your prototype and drink a ton of river water testing it. Then you realize that 8 of 10 startups fail; and you must ask yourself, “Do I have the grit to succeed?”. This answer is how a start-up founder defines either success or failure.

Tech startup lesson by V. Michael Santoro, Co-Founder of Vaetas

16. Determine if your business is scalable.

There’s a big difference between growth and scaling. Growth is expanding the business by increased use of resources while scaling is expanding the business with no additional resources. There are many successful unscalable businesses out there – McKinsey, Moleskine, etc. If you ever thought about scaling, the first thing to do is to figure out whether or not your business model is capable of it.

Business scalability lesson by Anna Polishchuk, Co-Founder at Lalafo 

17. Take inspiration from Kaizen. 

Kaizen ideology was coined by Toyota which believes everything can be and deserves to be improved.

With the devotion to improving a little bit every single day, any entrepreneur can accumulate incredible improvement and success. This is even more powerful if the entrepreneur is able to establish this ideology within the culture of their company.

Success advise by Kean Graham, CEO of MonetizeMore

18. Success comes from opportunities, not ideas.

There are lots of good startup ideas, but new entrepreneurs will find success from opportunities where they have a special advantage. For startups in established markets, find some non-obvious insider knowledge about a high-value problem. For startups in new markets, like the Blockchain, speed to market is the threshold to become an “expert”.

And, of course, new entrepreneurs need to understand what it would take to build an MVP (minimum viable product) – the cheaper the better. Most importantly, entrepreneurs need customers; as long as they’re building and planning, they just have an idea; once they can get someone to pay for the product, then they have a startup.

Startup advise by Mike Vladimer, co-founder of the IoT Studio at Orange Silicon Valley

19. Learn the importance of being lean.

Many tech startups start their business with an idea and a computer. Lots of young entrepreneurs worry about getting a fancy office, website, and all the “sexy startup” things when they need to focus on for generating revenue and building a bank account so the business can survive.

One other important aspect is the law of doubling. Young entrepreneurs should estimate the amount of time it will take them to be profitable and then double that estimate for a more realistic expectation of what it will take in terms of a time/effort commitment to getting the business profitable.

Tech startup lesson by Anthony Mongeluzo is the CEO of PCS

20. Get rid of team members who have weak skills.

In my business, I spent more time managing bad employees that finding new customers. That was a big mistake. It would have been better for everyone to let them the moment I figured they were probably not a good fit.

As soon as I let them go, the culture got stronger and the bar higher. “A” team people like to be surrounded by other stars. Also, I recommend NOT spending money on things like fancy brochures, letterhead, business cards, etc.

Until you know your business is launched I would say to put your budget into things that help fill your pipeline with customers.  Getting your domain name and a website up and running is key.

Your story will evolve as you find your market, so you need to look professional and have a website to be taken seriously, but embossed paper with watermarks and heavy card stock is not going to accelerate your sales cycle.

Advice on team building for startups by Paige Arnof-Fenn, founder & CEO of global marketing firm Mavens & Moguls

Looking for a domain name for your startup? Get it here!


21. Soft skills are important.

Success comes from merging your product and tech skills with a focus on what will get you to your business goals, and the application of soft skills (such as communications, leadership, sales) that you need to operate your business successfully.

All the successful businessmen such as Bill Gates, Mark Zuckerberg, Larry Ellison – they all have great soft skills. The good news is that soft skills are learnable skills. If you don’t have them, you should prioritize learning them early on in your entrepreneurial journey.

It will help you in everything – from leading your team to selling your product to obtaining your share of investor dollars.

Advice on soft skills for entrepreneurs by David Radin, CEO & Co-creator of Confirmed Instant Scheduler

22. Your subject-matter expertise is not the most important thing.

I’m a computer science engineer, so I thought that in my virtual reality startup was very important to focus on the technical features of our product, which was a solution for full-body VR. This way, we ignored things that are much more important, like:

  • Timing: We had an early prototype that could rise a lot of interest, but we waited too much to release it on the market because we wanted to add a lot of features to it. When we did it, it was too late.
  • Marketing: It is as important as the product. Social media, blogging, outreach to magazines, etc are all of paramount importance. You can make the most beautiful product, but if no one knows about it, you’re doomed to fail. Invest at least half of your time in marketing. HALF OF THE TIME;
  • Business: A startup is all about money. Think about how to monetize your product, how to get investments, how you can make your investors earn something from investing in you. Without money, you shut-down, it’s simple.
  • Product/market fit: You have to adjust your idea to obtain something that your customers are interested in buying.

Advice for tech startup founders by Antony Vitillo, owner of the successful AR/VR blog ‘The Ghost Howls’ 

23. Do one thing at a time.

When you’re building a startup, the task list can feel overwhelming. It is tempting to try to do everything at once, but the more you can narrow your focus and do one thing at a time and doing it well, the more successful you’ll be.

Time management tip for startup founders by Manisha, CEO and founder of CottageClass 

24. You need to have a team that is relentless.

It’s not enough to be talented. In a startup, you must have people who are obsessive. Also, keep asking yourself, “What are you optimizing for?” Focus on the one thing that makes your business/product shine to customers. Those two things are the most important aspects of building your company.

Team related advice for startup founders by Paul Burke, founder and CEO at RentHoop

25. Be the cheerleader, the HR liaison, the bad guy and sometimes the maid.

Having a smart, talented team that understands the bigger picture will help push your goals and objectives into motion. Never just assume that your team “gets it” or even has the same motivations as you.

Make sure you’re playing your part in helping them “get it”. It’s important to convey your passion for what you’re doing. My co-founder and I spend a lot of time talking about the educators who benefit from Educents, even sharing love mail on a regular basis so the team can celebrate our impact.

That kind of transparency inspires and aligns the team to our vision. And also, make sure you listen. Listening is a key component to communication. You cannot motivate a team if you haven’t listened to what makes them tick.

Perhaps you are missing super simple that makes the team want to work all night to get the job done. Another lesson I have learned in my 5 years as a venture-backed entrepreneur is to never underestimate how long the road can be.

Companies are not born overnight. It takes months, maybe years, of hard work to get off the ground. When you think the long nights are over, something else will come along that’s worth staying up for.

Leadership advice for tech startup founders by Kaitlyn Trabucco, founder and COO of Educents.com


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26. You will never be fully ready. 

Ask yourself, “If not me, then who? If not now, then when”. Sometimes we need to take a chance on ourselves, and the time is always now. One of my greatest lessons I learned in business was that there was never going to be a point that my company would be fully ready to scale until it just happened.

And when we began to have difficulties, it was important to stay calm, learn from best practices, and figure out a feasible solution as quickly as possible and start testing. You won’t know what works until you start testing and sometimes that could be a bit chaotic and scary, but that’s all a huge part of the fun of the entrepreneurial journey.

Lesson in startup scalability by Siqi Mou, founder of beauty chatbot HelloAva.

27. Make things as simple as possible.

The time you have as an entrepreneur is extremely limited, so based on this condition is that you should focus strictly on validating if your idea (business model) is feasible or not, has a future or not?

The most valuable key tip we learned in the last 9 years was that we should not have focused on things that don’t scale. Your most important goal is to validate whether or not your idea has a product/market fit.

Advice on feasibility for tech startup founders by Cristian Rennella, CEO & CoFounder of oMelhorTrato.com

28. Stay one step ahead.

We’ve changed and expanded our service offerings many times throughout the life of our business. The ability to adapt and innovate is extremely important in any technology related field. If you’re able to stay one step ahead, there’s a chance to prosper. This philosophy has helped Atlantic.Net to prosper ever since it was launched in 1994.

Growth tip for tech startup founders by Adnan Raja, Vice President of Marketing for Atlantic.Net

29. An epic failure on ABC’s Shark Tank can lead to an investment of over half a million dollars

After four tumultuous years of building my startup with the wrong partners, lots of bad decisions and some major rookie mistakes, I was determined to find a way to take my business to the next level … and what better way than to apply to ABC’s Shark Tank?

In September of 2013, I found myself walking down that scary shark infested hallway into a stare off with 5 of the harshest millionaire investors in the world.

When I proclaimed I was going to change the population with my reverse engineered online dating business, serial entrepreneur and Dallas Mavericks owner, Mark Cuban, rolled his eyes, called me delusional and immediately snapped, “I’m out.”

Billionaire investor, Kevin O’Leary, demanded that I quit my “hobby” and shoot my business—my passion– like a rabid dog. After getting shot down by all five Sharks, I looked them in the eye and said, “Trust that you’ll all see me again.”

Although those final bold words of mine ended up on the cutting room floor (adding insult to injury), in the 48 hours after the broadcast, Cheekd.com received a record-breaking 100K unique visitors and our inbox filled up with thousands of emails insisting that the “Sharks” were “out of their minds” for not investing. A little under 50 of those emails were from interested investors.

Since then, we’ve raised 5 times the amount I’d sought on the show. It was only a matter of time and I’m thankful I didn’t take the Sharks advice to quit and move on.

Advice on turning adversity into opportunity by Lori Cheek, founder and CEO at Mobile Bluetooth Dating App Cheekd. @cheekd


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30. Celebrate little wins.

Building startups are extremely hard and the only way to avoid burnout and keep a team energized is to celebrate the little wins. Speaking from experience, the hard times get very hard and it’s hard to feel excited unless you acknowledge the wins that do come along.

After a startup launches its product (usually this is less of a problem pre-launch because there is always a lot of optimism that things will go well post-launch), things either really take off or startups go into a trough of sorrow.

If things do take off, in the rare case this happens, the company is in a frantic panic to keep servers up or fill orders. It’s madness and can burn out the company very quickly if not careful. If things don’t go well and are slow and steady, it takes a lot of perseverance to iterate and build traction.

The wins are slow and infrequent. People will abandon if they don’t get excited about it and excitement comes from celebrating the little things.

Leadership advice for entrepreneurs by Sydney Liu, Co-founder of Commaful

31. It’s easier to succeed if you only revolutionize one thing at a time.

There are standard ways of building startups and running companies that every entrepreneur can learn and follow. This frees them up to focus on their game-changing product or service. Once they succeed, they can focus on revolutionizing something else.

Think about how Tony Hsieh at Zappos first built a shoe company so successful that Amazon bought it—and only then did he start experimenting with Holacracy to radically change the way the business is run. If he had tried to do both at the same time, he probably would have failed.

Advice on learning from others by Mike Lingle, serial entrepreneur and managing partner at 10xU, a division of Rokk3r Labs

32. Enjoy the ride.

So many people get caught up in the black and white of success and failure that they forget to enjoy what they are doing. If you created this idea, the odds are that you love what you created.

Forget about success and failure; find a comfortable spot in the gray area and work your butt off. Failure isn’t your worst enemy. It’s the fear of failure that is your enemy.

Lesson for entrepreneurs on how to keep going by Bo Lais, CEO and Founder of Lula

What is your most valuable learning as an entrepreneur? Share with us in the comments below! Use this startup name generator to search for the perfect name for your tech business.


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