Lessons Learned


Not all lessons learned have to be from your failure. Why not learn from the failures and mistakes of others? Here are some of the most important lessons our community of successful entrepreneurs have learned. Enjoy!


The Lessons

I would listen more. There are some wise people out there who truly believe in you and have your best interests in mind. Dispose of the youthful arrogance, and listen. Wisdom is king! Rick Martinez – Founder of Project Bink

I haven’t always been 100 percent honest with myself or my team. But this only leads to failure. Only when you face reality can you take the right action. If things aren’t going great, tell someone, then people can start helping you. Matthias Wagner – Founder of We Create Stuff

I made a hire based on friendship more than fit. The person hired definitely made great contributions to the company, but it just wasn’t the best path for either the person or the company. Six months later I was looking again and the sales pipeline was not where I wanted it to be and business did suffer. I overcame it by owning the failure and being solutions oriented about the solution with the team. Now the sales role is being played by someone who jumped over from project management and that person is doing great. T.J. Cook – CEO at CauseLabs

Ask for help sooner. Al Wynant – Co-founder and CEO of Eventinterface

I’ve had several learning experiences as an entrepreneur, but having my teammates leave is always difficult. The first one is tough, and the second one is usually pretty difficult, too. But by number three, you start to realize that it’s just a part of business. The biggest thing to remember is not to take it personally. Rather, focus your energy on what needs to happen moving forward. Jay Olsen – Founder of Jobsite Unite

In hindsight, we had a ridiculously complex pricing strategy at the beginning. Hospitals and patients were bewildered by the array of choices in healthcare providers we offered. They didn’t want choice so much as they wanted quality, so we listened. Now our pricing is very straightforward. Aschkan Abdul Malek – Founder of AlemHealth

I made the pretty big mistake of using my heart instead of my head when choosing a partner for one of my ventures. I really shouldn’t share too many details about the situation at this point. Let’s just say that this mistake created a huge mess that was difficult to clean up. This reinforced my belief that emotion clouds intuition, and any time you feel emotions about a decision, you need to step back, detach, and wait until you get into a neutral space before making the decision. Don Siclari – President of InChek

I failed to see things coming before they did. I was so consumed with what I was doing at the time that I didn’t jump on things quickly enough. We learned to pivot and got better at seeing things before the mass market did, but I wish I would’ve lifted my head up more. Jack Berlin – President and CEO of Accusoft

I failed to retain our original founding team members. It’s difficult to align individual growth trajectories with a quickly growing company. The people who take you from one phase of growth to another aren’t always the right fit for the next turn. Chris Kelly – Co-founder and President of Convene

Getting website security immediately upon starting my business. I found out the hard way, two years in, that shelling out the money to get my website protected is a very important investment. There’s nothing quite like the horror of having your website – your online business! – hacked. Lauren Tharp – Owner of LittleZotz Writing

If I were to start again, I would be a lot less concerned about what others think. Melissa Steach – Design & BDM of CORT Interiors

It took me too long to realize that what everyone else says, does, and believes is not as important as my gut. I would try to get some of my earlier, crazier ideas of the ground instead of waiting for validation. Isaac Morehouse – Founder and CEO of Praxis

If I could give my younger self some advice, it would be to “let go of anxiety, knowing your failures are leading to your greatest achievements and your disappointments are leading to your greatest joys” because today, I am definitely enjoying the journey! Mina Chang – CEO and President of Linking the World

I’d listen to the sage advice that it takes twice as long & costs twice as much money as you think to launch a new business! Heidi Zak – Creator of ThirdLove

I would have made growing my network a priority way earlier than I did. Especially as an entrepreneur, it’s so important to meet people who could potentially become business partners or even customers. Mike Peroni – COO of Content Raven

If I was to start again I would charge more as a consultant; I made many people a large sum of money and charged very little because at the time I didn’t have the courage to ask for what I was worth. Craig Handley – CEO & Co-Founder of Listen Up Español

We got distracted with several different offshoots and side projects and should have remained laser-focused on our core business. Haroon Mokhtarzada – Co-founder of Webs

When we got our company core values right and were willing to hire, fire, and promote based on them, everything changed. Robert Glazer – Founder of Acceleration Partners

One of my greatest failures was starting multiple businesses at once. At the time, I thought this was a great idea, because I figured if one of them didn’t work out, the others would pull ahead. But what I didn’t consider was that spreading yourself thin prevents you from growing any of your businesses. Vladimir Gendelman – Founder and CEO of Company Folders

I didn’t realize the amount of supportive communities out there for young people like the Harvard Project and Thiel Fellowship until only recently. As a young entrepreneur, it can be extremely easy to be distracted by school and lose momentum. Being in a community and interacting with like-minded people will seriously accelerate your venture. Elaine Truong – CEO of ReVolt

I would focus more on the marketing aspect of products and services. Having a great product or service can only get you so far. You have to be able to tell the story and elicit the appropriate response to ultimately get the sale. Matt Peterson – President and CEO of eFileCabinet

We refreshed our branding with an updated logo and new colors. We kept the nostalgic feel of the previous look but made it a little more clean and modern. This has opened doors to companies and influencers who may not have noticed us before. Amanda Henke – Owner of Annie B’s

I would probably have a lot more reasonable expectations about the business in general and not be so naïve about things – although I think a certain level of naiveté is almost a requirement to achieving success. Dan Goman – Founder and CEO of Ownzones

I’m diligent about letting things go after enough effort has been expended — a delicate balance exists between pursuing an endeavor enough and spinning your wheels. Zach Robbins – Founder and CEO at Leadnomics

I listened to my customers, and that has made all of the difference. Scott Monette – Founder of 100 Percent Wine

I would maybe focus on a specific sector or geography first, then go with a minimum viable product launch and scale from there. Vincent Molinari – Co-founder and CEO of GATE Global Impact

If I had to start again, I would be very honest with myself about the things I know and the things I don’t know. I would then find professionals to do the things that I don’t know or am not an expert in. Mike Juloya – Founder of Proof of Concept

Paying others to do what they do best frees up my time to do what I do best. Erin Belmore – Founder of Washington State Kitchen and Bath

Ironically, I’d say my biggest failure was in leadership. I used to think that all you had to do was hire great people in order to run a great company. But that’s not leadership; that’s recruitment. After hiring and subsequently losing more than 10 employees, I began to feel like a complete failure. This was a major turning point for me. Carey Rome – Founder and CEO of Cypress Resources

I would listen more. Listen to my gut and listen to the people that I trusted the most. Grant Glas – Founder and CEO of App Press