5 Critical Lessons I've Learned From Interviewing Over 100 Entrepreneurs

Entrepreneurship can be lonely. It’s hard to explain the amazing highs and soul-crushing lows to people who haven’t experienced them. When I had my first business, I was running it with my husband (that could be a whole other article!) so I had someone to bounce ideas off of, vent to and celebrate wins with. When I started my digital-marketing agency in 2016, it was just me.  

Which was great, but also … lonely. 

There’s nobody to hang out around the proverbial water cooler with, share exciting new ideas with or ask advice when needed. 

I wanted a community. 

I wanted support.

I wanted to know I wasn’t alone (or crazy) in what I was attempting to do. 

So the idea of creating a podcast was born. That was circa 2017, after about eight months of going at it alone. 

I actually launched the podcast in the summer of 2019. See the time difference there? Truth be told, I was scared to start it. I was not about to get out of my comfort zone and create something that could be criticized, laughed at, or worst of all, that no one cared about. 

Until I did. 

And as I look back over the list of entrepreneurs as I write this article, I can’t help but smile. And smile big. I have had the privilege of interviewing over 100 entrepreneurs from all across the U.S., Canada, the U.K. and New Zealand! I also have several in queue from Australia, India and other awesome countries across the globe.

And their stories are incredible. 

One of my very first guests suffered a pulmonary embolism and wasn’t sure what her future looked like or if she’d even make it home from the hospital to see her daughters again. She decided then and there to go for what she really wanted in life. And she is thriving. 

Another guest was diagnosed with cancer, beat it and decided to pursue her lifelong dream of opening her own business. And she’s crushing it (she actually has two incredible businesses).

Multiple guests were quickly moving up the corporate ladder, but it wasn’t cutting it for them. So they gave up their stable paychecks and followed their hearts into entrepreneurship. And they’re not looking back. 

And there are literally countless more inspiring stories, infinite nuggets and a feeling of community and support that makes me tear up at times. 

In interviewing these astounding humans, common themes started appearing. I noticed multiple entrepreneurs doing the same things and certain mindset similarities kept bubbling to the surface.

I have learned so much from my guests over the last two years, which has led to tremendous growth in my business, so here are the five most important lessons I’ve learned from interviewing more than 100 entrepreneurs.

1. Get comfortable with being uncomfortable

This is a big one. And I don’t think it ever gets easy; you just get used to doing things outside of your comfort zone. Remember above when it took me two years to start the podcast? Well, I finally realized that I just had to go for it. I almost canceled the first five interviews because I was so scared to do them. But I did. 

It’s not perfect. I literally Googled my way through how to start, edit and distribute a podcast. 

I’ve gotten one-star reviews. I’ve had people smirk when I say the name of my podcast. 

But you know what? 

I’ve generated revenue, referrals and recurring business from it (not to mention friends). It has been an experience I never could have imagined, and it is something I now look forward to each week. 

I still get nervous sometimes, especially when it’s a big guest. But the champagne helps! 

2. The importance of systems, routines and delegation

The entrepreneurs that I see enjoying the most success are the ones who have systems and routines in place. They have goals and have taken the time to brainstorm, create and execute systems that support them in achieving these goals. 

These can be a variety of different things such as onboarding, marketing or administrative duties. No one business is the same, but these owners have taken the time to evaluate their business and produce repeatable processes that help them save time, money and energy, which makes for a successful business.

Many of my guests also delegate tasks that don’t serve them, they don’t like doing, or they simply don’t have the time to do. 

You might not be in a place to delegate just yet, but you can create your systems as you grow so that when that time comes, they’re ready! You’ll be able to get your team member(s) going quickly because you’ve already put that work in. 

If you’d like to delegate but don’t quite have the budget just yet, consider hiring an intern to do some tasks or a VA for a few hours a week. 

3. Entrepreneurs are resilient and take risks

Before “pivot” became a buzzword during the pandemic, entrepreneurs were already well versed in adjusting, adapting and expanding when needed in their business. 

Many people were not prepared for the 2008 economic recession, but one of my guests quit their job and started their own business during that time and is still reaping the rewards!

Some thought it was suicide, but it paid off immensely. And continues to do so!

Though many entrepreneurs have to make decisions like that somewhat quickly, it doesn’t mean they don’t weigh the risks involved. The ones that have had to pivot in their business look at all angles and lean into their intuition. Sometimes leaning into your intuition can feel counterproductive, but it can create big results. 

Side note: Just look at all the ways businesses across the world have continued to adapt over the last year and a half. Outside curb seating with cute booths. Easy online ordering. DIY home kits. So many innovative ideas have emerged!

4. Entrepreneurs are constantly learning

Whether it’s from other entrepreneurs, books, courses or YouTube, 95% of the people that I interviewed talked about constantly learning. And it’s not all business either. Granted, most of it is, but they also take time to learn things that they are interested in. 

What stuck out to me (because I have this problem) is that they consume a lot of content, but they stay the course. They know there are a million things out there and learn about them, but if they don’t fit with their business, they move on. They don’t allow this learning to get in the way of what they’re doing. 

Having those systems and processes in place will help you stay on track when you start to waver. 

5. Entrepreneurs want more

They want to help more. 

They want to be with their family more. 

They want more financial freedom. 

They want more time to do the things they love. 

They are willing to do things that others won’t to get more — whatever that looks like for them.

The major takeaway here is that all of these things mentioned have to do with mindset. Each and every one of them. Start focusing on a success mindset, and your growth will happen much quicker!

Start putting yourself in uncomfortable situations  you will grow, I promise! It will be messy, imperfect and scary in the beginning, but when you look back from the other side, you will be so glad you started!

Begin creating your systems and processes to streamline your business now. Research interns and start delegating tasks you can afford to delegate. 

Know that you are strong (or you wouldn’t have become an entrepreneur in the first place!) and you can adapt to or bounce back from anything that happens. 

Take what you need from this article, implement it into your business and leave the rest. 

Never stop wanting more! 

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