Entrepreneurs share their Best and Worst decisions

by | Jun 25, 2021 | Blog

Neil Parker

Neil Parker

Founder & CTO of Lovecast

Single best decision:
Offer a free version of our product and make it better than any of our competitor’s paid products.

This has really made using Lovecast such a no-brainer choice for our users, and is the key factor to get us the 6000+ hosted weddings and raving reviews on App Store/Google Store and forums, despite not doing any advertisement at all.

And the extra benefit is, since users can easily try out Lovecast since it’s free, a large portion of them actually ended up purchasing the premium version because they’ve grown to like our product and our brand when using the free version.

Single worst decision:
We should invest more in marketing, especially PR marketing in the beginning. When COVID lockdown just happened, our competitors, despite having a way worse product, reached out to all sorts of news reporters claiming they have a solution for “virtual weddings”.

We however, were mostly focused on making our product absolutely perfect and the organic growth from satisfied users and their virtual guests.

This, in turn means we are almost invisible on search engines and are losing traffic to our competitors, even though people are raving about us in the forums.

So overall, what I learned is, organic growth is really nice, and we will keep building that, but we should also invest more in marketing as all our competitors are doing big marketing.


Shane Hurley

Shane Hurley

CEO of RedFynn Technologies

The worst decision I ever made was to trust people before they earned it. I focused on the good in everyone, only to have to live out the consequences of some poor choices.

Now, my trust must be earned, and that was the best decision I ever made.

This was a hard lesson for me to learn, but my battle scars forced me to take a rigorous look at people’s histories, priorities, motivations, and values.

I have a rather complicated and extensive hiring process that vets people, but I also put them to the test.

Once they have my trust and respect, I am all in.

Once I figured that out, I surrounded myself with excellent staff and bright partners who consistently surpass my expectations.

RedFynn Technologies

Lauri Kinkar

Lauri Kinkar

CEO of Messente

From my experience, I think one of the worst decisions I have ever made in our business is to not let go of employees even if I know they have a bad performance.

It’s because I feel bad about hurting their feelings.

I’m not saying that you have to fire an employee right away after they made a mistake. What I’m saying is, give them a chance to improve and guide them but if after some time, they aren’t still performing up to standards, it’s better to just let them go because it will hurt your company more than you think it would.

Tolerating the employees’ ways even if they are not meeting performance goals can also affect the morale and engagement of other employees.

I’ve realized that what I did was a mistake and from that moment on, I tried to be honest with underperforming employees while still being mindful of their feelings.

I made sure they understand why I think they are underperforming because sometimes, they are not aware of their bad performance. I know that my honesty can help them.

Maybe they can learn something from that experience.

For the best decision I made in business, I think it was deciding on implementing training on soft skills.

You would want employees who are reliable, resilient, and can adapt to changes during these uncertain times.

Training soft skills is important so that the employees can optimize their hard skills to the full extent.


Will Cannon

Will Cannon

CEO of Uplead

In the initial days of lockdowns, I was forced to hire two freelancers.

Little did I know that working remotely and offshore, freelancers were unable to turn up the work timely, yet still charged the agreed payment.

The platform intervened upon my report, yet they were unable to provide protection based on their work history.

That’s when I folded my sleeves and never turned back again!

I learned that while freelancing is great and it’s okay to hire them, make sure to always check their work history in terms of conflict/refund/payments before hiring them.


Ashni Christ

Ashni Christ

Founder of Stream Coach

My worst decision was not learning and getting started earlier.

I let fear and other people’s opinions hold me back from just starting.

This is possibly the most debilitating thought process new aspiring or new entrepreneurs have.

Ultimately you realize other people’s opinions don’t matter as long as you believe in your business.

The future you’re building is worth the effort through adversity.

My best decision was hiring a team.

I know as a founder/CEO that my time is limited.

As much as I wish it wasn’t true, I only have 24 hours in a day and 7 days in a week, and I can only do so much on my own.

Once I hired a team, my productivity exploded, projects got done faster, I was able to dedicate more time to high-level visionary work, and I got to start taking a day off each week.. I was living the dream!

A team will scale your output because you can’t afford to do it by yourself forever.

Stream Coach

Brad Schneider

Brad Schneider

CEO of Nomad Data

Worst Decision:
The worst decision I made was in my previous startup.. I chose to solve a problem that was extremely technically challenging, unifying data across hundreds of vendors into a single user interface.

The idea made sense back then and still makes sense today.

The problem is that the complexity is enormous.

Starting a new company to solve such a difficult problem requires a massive amount of capital.

The only way to effectively raise that much capital and still have employees own a reasonable amount is to be a celebrity-founder who can raise rounds at extremely high valuations.

What I’ve learned is that the first problem you want to solve and monetize at a startup is one that is as low risk as possible. The odds of success are already stacked so high against you.

Best Decision:
The best decision I made in my last business was not to be cheap when it comes to making employees happy.

High attrition can destroy a company in so many ways.

Each lost employee hurts morale, destroys culture, increasing training costs, adds additional recruitment time and cost.

I found that whatever money I spent to keep people happy and motivated always paid dividends.

Spending more money on an office created an environment people wanted to work in.
We would allow employees to customize every aspect of their workspace from their computer to their desk and chair.

We also spent thousands of dollars a month on coffee and snacks.

Despite the negative feedback I got from people externally to the company, our attrition was near zero.

As a result we had an incredible culture and employees that were motivated.

This led to so many other parts of the business being more successful.

Keeping people happy obviously isn’t only about money but it’s a strong signal to employees of how much you value them.

Nomad Data

About the Community

On the podcast, Sean talks with entrepreneurs about the reality of their struggle to succeed, as well as answering questions from the community, and sharing nuggets of wisdom from his own life.

Discover through these amazing episodes the courage to open your mind, heart, and soul to the world so you can be the best entrepreneur possible, respect the people you work with, and improve the world with your company while not hurting others or yourself in the process.

Sean Weisbrot

Sean Weisbrot

Sean is an entrepreneur, investor, and advisor based in SE Asia for over 12 years. He is passionate about Psychology and helping others improve themselves.

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