15 Entrepreneurs Share Their Dating Lessons Learned From Building A Business

15 Entrepreneurs Share Their Dating Lessons 

Learned From Building a Business

Building a life and building a business become intertwined, with or without or knowledge. Business and love can have so much in common. How long before you follow up after an interview, or how long do you leave before you text after a Tinder date? How different is the interaction between prospective business colleagues and potential partners? As Valentine’s day approaches, we asked 15 entrepreneurs what they learned from the business world about love, and how entrepreneurship took them into to the path of their Valentine.

Misha Kaura, Fashion Entrepreneur of Misha Kaura and Mishactiv and the Darlinghurst Garment Factory, and Upcoming Television Show Host 

 I think so much of what has made me a millionaire in the fashion industry is my obsession with remaining true to my vision, my values, and my belief system. A lot of people told me to do “sexier” dresses, or use crystals sourced from random places instead of Swarovski, but I’ve always remained true to my vision: building and growing my business around the highest quality craftsmanship in both the US and Europe. At the end of the day, you have to have faith in not only God but also your own judgment.  I have this same “research first, implement second” outlook toward dating. I’m very proud of my abstinent virginity, and the fact that I’ve done extensive research outside of my graduate school studies on what makes marriages last—I’ve read everything from academic papers in the Journal of Marriage and Family to Dr. Willard Harvey’s “His Needs, Her Needs,” to taking survey after survey, to graduating first in my class from not just in fashion school and graduate school but also cooking school. I’ve authored nine books, including one cookbook. Suffice it to say, I’m going to be the Stepford Superwife Supermom Superbusinesswoman. In life, intense focus, drive, and vision take you where you want to be and beginning with the end in mind is the best way forward. The purpose of dating is to get married, and I think when you’re upfront about your values and goals in life, the right guy will appreciate where you stand. I think a lot of guys see that I’m a successful businesswoman, abstinent virgin, bestselling author, former commercial model, and former beauty queen (I was Miss Utah 2015-2016), and get intimidated because I’ve succeeded on a grand level in every endeavor that matters, but I know that eventually like will attract like. I’ll end up with someone on my level—someone virtuous, driven, resourceful, amazing, innovative, empathetic, supportive, compassionate, and just as hardworking as me. 

Alex Hanifin, Alpine Start Foods CEO and Co-Founder 

Relationships are everything, and building a network of people who will support you on every level (and your company) is a game-changer. I was told by conventional HR departments that my extensive tattoos and young age would be a barrier to success in an office environment. So, I decided to choose environments that worked for me.  I learned how important it is to surround yourself with people that are rooting for you: peers, mentors, experts, friends, and partners– the people you call when shit hits the fan! The people that are down with the crazy schedules, the late hours, the early mornings and the sweet moments filled with success! Rejection can place us on the right path.  After high school, I didn't get into any of the schools I applied to. It pushed me to take the road less traveled and fueled my passion for food – a field that I might have neglected for another major, focus, etc. in college. I was able to dive right into the industry, taking internships at leading natural foods companies, learning hands-on skills from mentors, and honing a can-do attitude to make me even more qualified than many of my peers with degrees.  Like with dating, especially in today's swipe scene, business decisions can often hinge on appearance and first impressions. I was told by conventional HR departments that my tattoos and age would hinder my success, so I surrounded myself with people who supported me, no matter what. Peers, mentors, experts, friends, and, yes, even significant others. It's a good reminder to look past the surface and embrace anyone who you'd call when things get ugly. You also learn to deal with rejection when you build a business. It's a rocky road, and you have to develop a sense of self and purpose, so when you hear 'no,' it rolls right off you. 

Stacy CaprioFounder Accelerated Growth Marketing

The biggest lesson I've learned is that you have to be intentional in both business and dating to succeed. For example, if you don't specifically decide to make X revenue in X months with X business type then you will never reach your goals. It's the same with dating, if you don't intentionally decide to put yourself in situations where you will be surrounded by attractive members of the opposite sex and decide to intentionally talk to and find one to date, then it is much less likely it will actually happen.

Beth Minardi, Creator of Beth Minardi Signature Hair Color and Hair Care

 Do a background check: Before you let someone into your boardroom or bedroom, check their background. So many people misrepresent their job history, and they’re likely to do the same in a relationship. This is especially important when dating—or hiring—long distance. I even experienced someone using a fictitious address to attract opportunity. Beware of Bait & Switch/Meet in Person as soon as possible: I was surprised after conducting phone interviews with a job candidate who talked the perfect game only to learn later that someone else actually did the phone interview. You can imagine that the same thing can happen when meeting potential dates online. Check their staying power: If their resume or LinkedIn profile is sketchy and most of their jobs (think professional relationships) have lasted less than a year, it’s likely that their dating history follows suit. Beware of ghosting: Someone who commits to a professional or personal meeting or phone conference, but then usually cancels at the last minute is often not in the situation he claims. Seek positive people: If they bash everyone and everything from their prior employment, chances are they do the same about their exes. Since that might be you or your company one day, avoid bashers at all costs. Too much, too soon: I’ve worked with people who asked for more commitment and recognition in their first month of employment—when they could barely handle their responsibilities. If you’re dating someone who wants too much, too soon, proceed with caution and don’t get swept away by what you want to hear. If it sounds too good to be true, it most likely is. Know thyself. For business or love, seek a partner who is self aware. Those are the people who can grow with your company—and you—into a long-lasting future.

Amy Shepsman, Jewelry Designer For Flaka Jewelry  

I was just beginning to feel confident in my decision to start my own business and started taking the steps to create prototypes and models for what would eventually become Flaca's first collection.  This more or less coincided with a breakup and with pleas from my (desperate Jewish) mother to join JDate. On my second or third date with this particular guy, I knew he wasn't for me. I was focused on my new career especially after coming off a few smaller "Tupperware parties" where I had sold my jewelry with great success, and I was pumped and very focused.   We went out for dinner where I ordered a cheeseburger (JDate sin number 1!) and he ordered a salad.  When the food was brought over, the salad was placed in front of me and the burger in front of him (Jdate sin number 2!), which was, for some reason, particularly upsetting to him. I reached over, swapped plates and began to eat.  I felt, even in the early stages of my business, confident in who I was, the person I had become and the choices I was making.  I often find that because I am a young woman, people assume I sit in front of a TV stringing beads as my "jewelry business."  I've learned to always order the cheeseburger (even if its on a JDate!) and stand up for myself and my hard work.  My elevator pitch for Flaca includes our relationship with Bergdorfs, Neimans and the fact I was featured as Forbes 30 Under 30 without sounding condescending because I worked hard for those stats and don't need to apologize for that.  Within the last few weeks an older gentleman who learned I owned a jewelry business remarked, "wow, that must be so easy, my wife loves jewelry!"  I calmly smiled and said, well it's certainly not easy but I'm glad I make it look that way.  

Amy Barnouw, Co-Founder and CEO of Planet Fuel 

The best lesson I learned  from building my business is how important it is to figure out what motivates and grounds you. In a business, or in a relationship, it can be easy to struggle through hard decisions and bad days so it is important to look at what kind of support you need in order to push through and then learn from those times. Having someone who can help motivate you, remind you to take your own advice, and then celebrate your successes, is the foundation for a strong partnership, whether personal or professional.

Vanessa James, Founder of VJMedia

Building a business from the ground up requires all of your attention and time, especially in the initial phase when many things are trial and error. This can be very challenging on your dating life as I'm sure many women can attest to. How I've learned to balance the two is to simply carve out time for dating without distractions from work. I tend to plan date nights with my partner a week in advance and that gives me the ability to blaze through my work anticipating our meet-up/date.  I also try my best to take the date out of my work environment so I can completely mentally break away and am able to focus solely on him. What many men won't admit is that it can be quite challenging dating a female entrepreneur. He has to have the patience and the stamina to keep up. A tip that I share with girlfriends and other female entrepreneurs is, let your partner plan the date night sometimes. It's not only sexy to see what they come up with, but it also can show you how detailed they are about planning things out with you in mind, which again is a huge turn on. What female entrepreneurs want more than anything, because we tend to be so detailed, is for someone to take that pressure off so that we the get together happens, we as women, can kick back and enjoy the moment and be all in! 

Nothing spells confidence than a man who knows when to lead and that same man knowing when to be lead. 

Maleeka T. Hollaway, Creative Brand Consultant

My most successful relationship thus far has been with a guy who also has a business. We understand the daily grind, the importance of flexible schedules and we sometimes get to tag team projects together. I’d tell any business owner to find someone whose hustle and grind matches yours. This way, you won’t have to explain your crazy work schedule and he’ll know that when you make time to go out with him, it’s because you want to not because you need to. 

Dora Lau, Founder of Curvy Couture

Break up with your bra (or business partner), if it's not supportive, doesn't understand your needs, and gives you pain.  You'll be better off taking the time to find what you need and moving forward on a positive looking path.

Amber Venz Box, President and Co-Founder of rewardStyle and LIKEtoKNOW.it

Find a co-founder who completes your skill set. Baxter and I are yin and yang when it comes to our skills. He oversees the technical side of the business while I oversee the marketing side. We sit next to each other in meetings and really balance each other’s ideas. 

Nothing spells confidence than a man who knows when to lead and that same man knowing when to be lead. 

Catherine Delcin, Delcin Consulting Group

The most important dating lesson that I have learned is to curtail the over sharing of my vision. Being a visionary and being a “viable mate prospect” are not always mutually exclusive. It’s the same as the common parlance “how are you?” most people ask but they don’t really want to know the details. Imagine if you took the time to tell everyone who asks how you really are besides “good.” People would be taken back. By the same taken, do not overshare your plans in the early stages of dating. Instead, provide a succinct overview without sharing the actual plans. There will be plenty of time for that later.

 Jill Salzman, runs The Founding Moms and Co-Host of the Breaking Down Your Business podcast.

Ask and ye shall receive. If you don’t ask for what you want, you won’t get it. It’s not a time to be humble or coy or play dumb. Put it out there — put it all out there — and you’ll feel way more satisfied…in your endeavors. Say “no” more often. When you say “yes” to any opportunity for a bad reason, you’ll regret it. Don’t say “yes” because you feel badly for the person who asked. Don’t say “yes” because you have FOMO and worry you’ll miss out on something that might be awesome. Don’t say “yes” when you know what the answer is. The answer, more likely than not, is “no".

Terré Holmes, Transformational Speaker, Master Business Strategist at EnvisionU, Founder of the LIVE, Bounce Back Experience and Coin Clarity Course 

You must make an asserted effort to nurture the relationship before you start putting demands on it.  I'm in sales and marketing and I can't ask my clients for a commitment until I put in some work  I can't even expect a client to want to take a look at what I'm offering if I haven't first added value. In dating, it's no different.  Don't ask a woman to your house or vice versa, if you haven't made her comfortable outside of your homes, built a rapport, and put in some hours. Talk less and listen more.  In both business and relationships you'll learn more about the other person, so that way you can decide if you both want to do "business" or not. OR, as far as a relationship goes, if you only take the time to listen you'll find that the person's either worth your investment or not.  The problem in both business and relationships is when people hear only what they want to hear. Don't be afraid to close to deal.  The truth is, in life, you don't get what you want, you get what you are.  If you want something say it.  You have certain expectations, voice them.  I've found that if you're transparent from the beginning and you put your cards on the table, you'll find that either it's for you or it's not.  The quicker you figure that out, the quicker you can either get to building something substantial or moving on to something more in alignment to who and what you are.


Sabya Clarke, Virtual Reality Director, Producer and Writer

The best dating lesson I've learned from building a business is to check online reviews. What's the first thing you do when you've been introduced to a new product or service? You go online. You check out the reviews, which helps you to decide whether you want to invest your money or move on. Dating is the same process. Go online. Check out social media pages and the general online reputation of the person you're dating. Yes, it's true that some things are fake, and you still have to get to know who you're dating. However, you can at least steer clear people who  consistently show that they are irresponsible with their life.

Meg Marrs, Blogger

One lesson I've learned that has helped with dating and my business is to do my homework and try to find an overlapping connection as best I can. When you spend a lot of time scouring Bumble and OKCupid, it can be easy to forget if you're getting drinks with the guy who just got back from a month in Asia, or the programmer who just left his job to start freelancing. Make sure to go through your date's profile before you walk into the bar and remind yourself what you've talked about virtually, what he's been up to, etc. Do your best to find something you can connect over - does he also have a passion for so-bad-they're-good movies like The Room? Does he have a bucket list equally epic as yours of countries to visit? Finding something to connect over can make a boring date interesting and compelling. The same goes for business too of course! I spend a lot of time e-mailing other bloggers trying to get links to my own website. I always try to do a bit of extra research and find something I can connect with. For example, where did the blogger go to school? What did they study in college? Do they have a dog? I'll never forget one e-mail from a blogger who sad, "Wow, I get a lot of outreach emails, but no one's ever bothered to mention Joker (her dog's name) before. I'm really impressed! And yes, I'd love to link to your website." It pays to do your research and make a personal connection!

Aly Walansky

Aly Walansky is a freelance lifestyles writer based in New York City, who contributes regularly to iVillage, SheKnows.com, xoJane, Huffington Post, and The Fashion Spot as well as many other print and web outlets.

1 Comment
  1. As an entrepreneur, my most challenging issues are the issue of making decisions. I always feel that I am not making the best decision alone. This has been an issue for my business so far but I wish to handle it.

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