Entrepreneur Life

The personal side of starting and running a business.

Advice From Entrepreneurs On All Things Personal

Below you will find the big list of all the questions we’ve asked entrepreneurs, as well as those same questions broken out into categories. If you have a question or topic you would like to suggest please let us know!

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12 Responses
What do you do to maintain your relationship with your spouse?
Spending money on a regular babysitter to go out with my wife is some of (if not THE) best money you can spend after you have kids. You get so busy with kids and work that it’s really, really easy for your relationship to not get prioritized like you want it to. And in today’s kid-centric culture it’s a hard thing to fight. But you know what’s more important than playdates, making progress at your work or even seeing your kids every single day? Spending time with your spouse. I’ve heard it said that the best thing you can do for your kids is to have a great relationship with your wife/husband/partner and I think it’s 100% the truth. So spend more than you think you need on childcare and making sure you get regular time to connect and recharge without being distracted by the pull of your kids. It’ll... Read the rest of the answer here.

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11 Responses
How did your work habits change after you had a kid(s)?
When my son was born- I had top tier status on 2 airlines attending to clients in what was a small consulting practice. I could not get off the road in a substantial way, so I made a few changes to remain connected: 1. When I was home. I was home. No laptop, no work as long as my wife and son were awake. We created as many opportunities for family time or for father and son time as we could. 2. I was an early adopter for remote video and no matter the time zone, made certain that we SAW each other as well as talked daily. Conversation was not much- but presence mattered. 3. As my son got old enough to get geography and mail and such, I started sending pictures, post cards (snail mail) and sharing stories of the road- good and bad. At 3 my son... Read the rest of the answer here.

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10 Responses
What is the #1 piece of advice you would give an entrepreneur who is about to be a parent on how to balance those two worlds?
When I became a father, my business (my first baby) was in a good place. I tell people my busiess is now in kindergarten and under “adult supervision.” So the timing was really good to be able to focus less time and energy on my business than I did in the startup years and to shift that focus more to my children and family for a nice balance. I have more time and energy constraints now as an entrepreneur and father, which I think is actually a very good thing. I have obsessive and workaholic tendencies and now I simply can’t (or won’t) do the things I did in the beginning, which gives me such a better perspective on life. I’ve been able to focus on empowering and mentoring others in the business to do some of the things I frankly shouldn’t have been doing. I prioritize my time and... Read the rest of the answer here.

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7 Responses
Has being a parent helped you become a better entrepreneur and business owner? How?
With kids, they are growing slow. When we interact with adults, we are always impatient on them to understand a concept. With Kids, we don’t have a choice. Same way, we are most of the time impatient with our business. We want it to grow fast, but the reality is it takes time just like a kid which learns to walk, talk and understand slowly. It takes years for you to communicate what you had in mind to them. With this realisation, my agitation and impatiences were improved tremendously.

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3 Responses
What is the #1 piece of advice you would give to an entrepreneur who is about to be a parent?
Your life is about to change. You are now responsible for someone else so what you have to give in terms of time and money now has to be shared with your new child. Nights with little to no sleep, running errands, more house chores are just a few of the inconveniences that will now be occurring regularly that you did not have to deal with prior to your new child. I found that If I set aside time in the day or night where I could give myself 100% to my kids it worked better than when I tried to do work while being with my kids. If possible have twins because if you can raise twins you can do anything!

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1 Responses
After you sold your business how did that affect you personally?
After the first big exit, I had a big loss of identity. I was young and I felt lost as the business had heavily defined me. It was weird to go from having a pretty amazing title and reputation to not having that and feeling invisible. In the long run, it was good for me, but in the short term, I was pretty moody and not sure what to do with my life. It took me a good 6 to 12 months to get out of my funk and figure out the next step. Long term, it has a super positive effect on me and helped me build a better identity not based around just my work. When I had the next big exit there were no issues as I knew who I was by then, and I knew what to expect. Plus I had a family and having them... Read the rest of the answer here.

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1 Responses
Finances can be a huge stress, how do you and your spouse handle the ups and downs that being an entrepreneur can bring to finances?
We’ve been married 4 years and we started doing a family budget as soon as we got married. My wife is not a finance nerd (like me) so it was good for her to understand our retirement planning and we do a little budget meeting at the end of each month. The meeting really helps us see where we are spending money and talk about it so that we are on the same page. I don’t think we have had any fights about money except a decision to buy a house which I rushed too much. I’ve learned she needs a lot of time to wrap her mind around something, whereas for me it takes a few seconds and then I am ready to go for it. I think we make a good team 🙂 I am lucky in that I had a big exit right after we got married,... Read the rest of the answer here.

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1 Responses
Have ever seen a therapist? What made you decide to go? Was it helpful?
Yep, I have seen a Therapist a few times, and each experience was helpful. In 2014 I had a year from hell, my relationship with my business partner disintegrated, I was told I had cancer, tumors, or Crohn’s disease (in that order), and I got diagnosed with an annular disc tear and couldn’t do any sports other than walking and swimming for 9 months. I was a wreck and just barely keeping it together. I was dating my future wife at the time and also got engaged and married that year. I wish I had thought about getting some help earlier, but I was so out of wack I did not even see it as an option. My future wife asked me to go late in the year about 10 months into it and I wish I had gone so much sooner. I went for about 6 weeks and it... Read the rest of the answer here.

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1 Responses
How much vacation do you take per year at your business? How did that change over time?
When the company was young I did not take as much time off. It took about 1.5 years to get the business to a solid place financially and with the team. Once we hit that point I was fine taking a month of time off to travel while my business partner watched over things. As the company grew to 100+ people I took about 8 weeks off per year. I love having big blocks of time to explore new places. I’d stay on top of email during those trips to some degree but I was pretty “off” during those periods. I had an amazing management team and business partner so I never worried about being up in the mountains or totally off the grid if I wanted. I just started a new business now and my partner and I are planning to take off 4 weeks including all holidays and... Read the rest of the answer here.

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1 Responses
What do you do to stay in shape while running a business?
When I was single it was easy to stay in shape as I loved to run and didn’t have a rigid schedule. Usually, I would end my day with an hour long run outside or on the treadmill if it was winter. And, I played a fair bit of organized sports as well. I hurt my back about 5 years ago and I had to stop running. I started doing rehab and hiking to keep myself fit. After I got married and had a kid it was harder as I wanted to hang out with them and I had less time. So, I changed my schedule and I wake up at 5 am and do 30 minutes of rehab/strength training, and then a 40 to 60 min bike ride indoors (Zwift). Starting the day with a workout like that just makes everything in my life good. I am not a... Read the rest of the answer here.

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1 Responses
What does retirement look like to you as an entrepreneur?
I just turned 37 and that is a hard one to answer as it seems pretty far off. I want to keep building and running businesses as I get older. I want to be at the point in my career where I focus on the big picture and product, and less of the nitty gritty that a team can handle without me. I’d like to put in 4 to 6 hours of high-level work a day and trust my team to handle the rest. For time outside of that, I’d like to help other entrepreneurs “entrepreneur”. I am still working on ideas for how I want to do that. And, spending a lot of time with my wife and son, and read a lot of books in beautiful locations. My wife and I both love to travel so I would like to travel quite a bit.

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1 Responses
What does work life balance mean for you as an entrepreneur?
It means that I don’t lose sight of what is important in my life and get out of balance over the long term. I love my work, and sometimes balance means a week of 12 hour work days and almost no time for me or my family. And, balance can also be a week of 4 hour work days and lots of time with my family. I have a pretty serious list of what I want to see and experience in the world on my own and with my family, and making sure those adventures happen is key. If I only worked I would go crazy and get burned out. I want to go to my death content with the life I have lived and that is a great benchmark to check in on every 6 months. When I was younger I would work so much and so hard that... Read the rest of the answer here.

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