Biggest Regret

What Is Your Biggest Regret?

This article is all about entrepreneurs’ biggest regret when it comes to business.

I got the opportunity to speak with 50 entrepreneurs from around the world. I asked them “What is their biggest regret”?

It is quite astonishing to see the answers and I wanted to share them with you all.

Bunny Dachs – Bunny’s Home Care

I’d consider the time before I set up my home care agency in the middle of this year as my biggest regret because I had doubted myself if I’d be successful. But when I perceived and became confident that I’d be following my passion for serving the elderly, I knew right then on the first day that I’m on the right track.

Vinoth AJ – Apoyo Corp

Even a good business strategy needs sufficient time to hit success. Stop changing your tactics more often and give the time they deserve to judge the success. The absence of having an alternate strategy can cost you time and money to recover from a failed plan.

Paige Arnof- Fenn

I started a global marketing and branding firm 18 years ago. My biggest challenge was not realizing that the people you start with are not always the ones who grow with you.  

The hardest lesson I learned when I started my company is not getting rid of weak people earlier than I did in the first few years of my business.  I spent more time managing them than finding new customers.  I knew in my gut they were not up to snuff but out of loyalty to them, I let them hang around much longer than they should have.  

It would have been better for everyone to let them go as soon as the signs were there.  They became more insecure and threatened as we grew which was not productive for the team.  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.  It is true that you should hire slowly and fire quickly.  I did not make that mistake again later on so I learned it well the first time.  I wish I had known it even earlier though but lesson learned for sure!  

Adam Hempenstall – Better Proposals

My biggest regret in my business is that I didn’t delegate enough early on. As the company was growing, I wanted to do everything on my own because I was convinced that I would do the best job myself. Big mistake, as I learned later on when I made my first few hires.

Nikola Baldikov – Brosix

One of the biggest lessons I have learned since I’ve been in business is that you simply should not undersell yourself, assuming that price is always the driving factor for customers.

After coming across research that demonstrates that customers see products that are significantly cheaper than competitors’ ones as unreliable, we decided to change our approach and increased the cost of our product significantly. Surprisingly, we found that the total number of conversions remained stable. So this is a lesson I wish I’ve learned earlier in life.

Aqsa Tabassam – Brandnic

I remained more focused on product development instead of customer-centric. As I had less worked on personalization and customer retention, it became my biggest regret. 

I have a product but not as many customers as it should be to generate a balanced revenue. 

I learned to value the customer more. These are the assets; we need to put ourselves in their shoes to bring innovation in products.

Gary Stevens – Hosting Canada

My biggest regret in my career was taking my time to adapt. While this has happened several times and probably will happen again, I still kick myself over the missed opportunities that came from stubbornness. My business was up and running before the social media marketing boom began.

At first, we resisted and stuck with the traditional avenues of marketing. This delay didn’t hold us back too much. I look back on the awareness we could have built, the money and time that could have been saved, and all those we could have employed just by accepting the changing times.

Matthew Meier – Max Tour

My biggest regret when it comes to my business is not selecting a name that we could secure the rights to the .com domain. We chose our name, then settled for the .co domain, but ideally, we would have checked about the availability of the .com domain before choosing our name.

Kean Graham – MonetizeMore

If I could go back in time, I would advise my younger self to hire our current CTO two years earlier. Our current CTO has done an incredible job resurrecting our technology stack and putting the technology in a position to achieve high levels of innovation. 

If I were to hire our current CTO two years earlier, I would have been able to avoid a horrible business partnership and a Google account ban that cost over $2M. More importantly, though, MonetizeMore would be two years ahead of where it is today. Our current CTO and CPO have done an incredible job catching up on our technology to get MonetizeMore to be amongst the trailblazers in the industry. However, I could only imagine the lead MonetizeMore would have if we brought our CTO onboard two years earlier.

Sean Dudayev

My biggest regret when it comes to my business is usually the things I haven’t done. Looking back I wish I would have double down on everything that was working and eliminated any effort on everything that wasn’t. Putting that rule into effect early on would’ve made a huge difference. The bright side is, that it is a lesson we have learned and are implementing now. Onwards and upwards!

Tom Matun – Powder Mix Direct

My biggest regret is trying to diversify rather than double down. Although it goes against conventional wisdom, it’s usually best to put all of your eggs in one basket and give that basket your full attention.


I would say my biggest regret is outsourcing my employees offshore. You think outsourcing is cheaper but in the long run, it can cost you much more. Furthermore, you can have difficulty supervising them due to the fact they are remote employees and you don’t have the same control and accountability as you would with employees that work for you locally.

Viola Eva – Flow SEO

Being an entrepreneur and a female founder, I’ve come through a lot of diversity, so I’ve become accustomed to really pushing through to get to the root of any problem, and it can be difficult to pivot when you’re so invested. Yet, that is exactly what must happen in today’s current business environment – you must be really innovative and ready to go back to the drawing board at a moment’s notice!

Andrea Loubier – Mailbird

I don’t have a lot of regrets about life in general, but I think it is increasingly difficult for entrepreneurs to delegate once their business is up and running. However, I learned that if I am not 100% the best person for the job, I am much better passing a particular task to a member of my team – anything else is a disservice to the client.

Josh Ladick – GSA Focus

My biggest regret has been dragging my feet to bring good people and companies in to do parts of my job that I do not like. I neglect what I do not enjoy, and the company has suffered as a result.

Earl White – House Heroes

I regret delaying content marketing. Organic search – with a focus on content – has been our most successful marketing channel. We waited a year to fully commit to content marketing. Once we began driving traffic to our site via our blog, business picked up immediately.

Kayla Pendleton

One of my biggest regrets in business was not being able to keep my first employee for very long because I had underestimated how much cash it would take in the beginning. Fortunately, she went on to great things and my business is rapidly growing two years later, but I still wish she was part of my organization!

Jana Mowrer – Health Wins

My biggest regret has been not serving as many people as I possibly could with the gifts/resources I have been given. I constantly work to overcome this daily by playing the non-zero day game where I do at least one small thing each and every day to get me to my long-term goal of helping more clients.

Janie J

My biggest regret in business was always having the “lack” mentality and always thinking there was “never enough money.” So I worked incredibly hard my entire adult life, even while raising a family, and I missed out on a lot of things, including living my own life. 

Vid Lamonte’ Buggs Jr

I live a life of no regrets. However, if I could go back and change one thing, I would have become an entrepreneur while I was either in college or right out of college. 

Robyn Flint – Expert Insurance Reviews

Owning three businesses has not come without heartache. My biggest regret in business is starting a business with a friend. Money and friendships do not blend well. They should be kept separate.

Kelly Reddington

I’d have to say my biggest regret when it comes to business was just not starting early enough! I fell into a trap early on of thinking “I need to know everything about THIS or THAT” when in reality, you can still get pretty far on incomplete information. I regret sitting around on the idea for over 2 years before actually jumping into the ring and going after it!

Mac Fadra – Maxim Hair Restoration

It’s ironic and contrarian that in a free market economy such as the U.S., the business environment is becoming increasingly regulated, particularly in health care, financial services, energy, education, and other sectors. Compliance is becoming an increasingly valuable and sought-after skill and expertise for present-day managers at all levels. With some 20/20 hindsight, leaders with a legal background in their arsenal combined with their business education and experience could not only have a competitive edge but make their jobs a lot easier. I know I wish I had studied more law classes or even pursued a law degree to aid me in my current role, so that would be a big regret of mine.

Carsten Schaefer – Crowdy

My biggest regret when it comes to business is not launching earlier. I knew I had a great idea, but by the time I launched my own app, there were several competitors that came up with something similar. I know I could have done better, but I just didn’t have the bravery to launch at the right time.

Tim Fox

My biggest business regret is starting my business journey late because of underestimating myself. I kept waiting for the right time, but the truth is there is no right time. Every second is an opportunity, and the risk factor always remains. If you have a business mindset, you have to kickstart your business ASAP by using the resources you have. Start from where you can to reach where you want to be.

Dane Kolbaba – Watchdog Pest Control

It is a shame but the biggest regret I have in business is trusting partners/investors too much. It’s one thing to get in an argument with someone and just leave without seeing them again. It’s a totally different story when you don’t get along with someone that owns half your company!

Jonathon Narvey – Mind Meld PR

I regret not switching over to the cloud sooner. We used to offer an on-premise software solution that required custom configuration and a lengthy onboarding. Sales were not easy. We switched to a cloud SaaS offering and with an almost instant onboarding, we’ve recently sailed past the 1,000 enterprise client milestone. The lesson for me: do your due diligence with new technology, but when you can see it works for you, move fast.

Kimberly Rath – Talent Plus

I don’t spend much time looking in the rearview mirror, there have certainly been tough times. In the early 2000s, the largest part of our business was in hospitality, and after 9/11 that industry was hurting. All we could do was continue to demonstrate the care and concern we had for our client partners. At the same time, we broadened our horizons and began looking at other industries that were invested in their end-user experience.

The Recession (2007/08) was another tough time because our corporate headquarters was in the middle of America, we didn’t feel it until later, but our compassion extended to our clients on the west and east coasts who experienced it sooner and more deeply. Anyone who has started a business knows that its successes and failures become part of your DNA.

My dad had his own business and I saw the level of customer service he provided to his clients – anytime they needed assistance. We have many clients who have been with us through our tenure today at Talent Plus and they have become friends and passionate stakeholders in our success and we have become the same for them and their organizations and/or their careers.

I have a devotion to our associates and clients and out of this devotion, spend a great deal of time thinking about them. It’s how our world gets better – by people feeling significant and cared for. As well, I hope that they were able to see that out of a great sense of mission and dedication, is the ability to make a difference.

Ryan Turner

We started our business in 2005, and at the time this was not apparent. Only in hindsight have I realized that I wish I had worked for a larger organization to gain management experience before starting our own agency. 

I think this would have better prepared me to manage labor as a key component in pricing our services.

Ryan Kolar

My biggest regret when it comes to business is that we thought we had enough. Enough clients, enough revenue, enough capital reserve, and/or enough investors are NEVER enough.

Roth Wilson – Tech Underworld

Unstable work-life balance, many people think about a business that requires 6-10 hours a day, and it started to work. These guys need to get a life, though! Business Work-life balance is always challenging to strike, and almost every entrepreneur suffers from this. I have been running a business of Gift packaging for ten years. Whatever schedule or calendar I had marked for the month, it tends to change each day. Subsequently, this disrupts and dismantles the equilibrium of my daily life. This is my biggest regret in business. If you want to retain long-lasting business sanity, It’s necessary to maintain a work-life balance.

Manny Vetti – Back Taxes Help

My biggest regret was starting a business with partners and not having a written partnership agreement in place. All was great for the first few years until visions changed. We all wanted out of the partnership to pursue our own visions but didn’t have a clearly defined way to do so.

The freedom I wanted from owning a business was gone, and I was trapped and fighting for that freedom back. The stress took a major toll on me and set me back a couple of years from pursuing ideas of my own. I realized that no matter how confident you are in your partners and business idea, always have a partnership agreement in place before moving forward.

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