Dating an entrepreneur could either be the most exhilarating adventure of your life, or it could drive you absolutely insane.
If you are currently dating someone who is building a business, you might find yourself confused. You might be asking, “Are they psychologically off? Why do they act like this? Do they love the business more than me?”
To save your sanity—and potentially your relationship—here are the 15 brutal truths you need to know about how entrepreneurs are wired, followed by advice directly from the spouse of a highly successful CEO.
1. Their Emotions Fluctuate Wildly
Entrepreneurs can be talking to you one moment, incredibly happy, and an hour later, they are emotionally drained or absolutely ticked off. Why? Their brains are wired to be highly sensitive to the details of their business. They experience the highs and lows deeply. If you haven’t read The Hypomanic Edge or A First-Rate Madness, they are highly recommended to understand this unique psychology.
2. It’s Bust or All-In (The Delayed Gratification)
If you are used to dating someone with consistent cash flow, buckle up. An entrepreneur might make $50,000 one month and $4,000 the next. There is a massive delayed gratification period—usually three to five years of financial pain—before the victory shows up. If you can stand by them when they have absolutely nothing, you will earn an indescribable, lifelong loyalty from them.
3. They Need Solitude to Survive
Sometimes, an entrepreneur just needs to disappear for a day—not to cheat, not because they are mad at you, but to gain back their sanity. Their “product” is often people and numbers, which means their emotions are constantly being pulled in a hundred directions. Don’t be offended if they need to sit in silence for four hours on a Sunday; it actually helps the relationship.
4. The 9-to-5 Schedule Does Not Exist
If the person you are dating clocks out at 5:00 PM every day and refuses to check their phone, they are likely an executive, not an entrepreneur. True entrepreneurs are constantly in the hunt. The drive to create never stops, and the outcome isn’t always about money; it’s about how they are fundamentally wired.
The Fix: If you want their time, put it on the calendar. Treat date night like a mandatory board meeting and remind them constantly.
5. They Rarely Ever Clock Out
You could be sitting at a romantic dinner, and suddenly, they are gone. Not physically, but mentally. They just saw a manager do something that sparked an idea for their own company, and their brain went to work. It isn’t that they don’t care about you; they simply cannot turn their brain off.
6. They Will Resent Ultimatums
If you say, “It’s either me or the business,” you are essentially telling an entrepreneur, “It’s either me or your right arm.” Do not ask an entrepreneur to change their DNA to be with you. If they do change for you, they will eventually deeply resent you for it.
7. They Will Miss Major Events
Entrepreneurs operate on a shot clock. If they don’t make the business work, it goes under. Because of this, they are going to miss events, parties, and dinners.
- The Fix: Tell them the absolute non-negotiables (Thanksgiving, your birthday, your child’s graduation) well in advance. Let them work through the rest.
8. They Talk to Strangers… A Lot
When you go out, they will strike up conversations with waitresses, valets, and random people at the bar. They are not flirting; they are intensely curious. They view every interaction as an opportunity to learn something new.
9. They Ask a Million Questions
Much like a three-year-old constantly asking “why,” entrepreneurs are always seeking feedback. “What did you think of that? Could I have done that better? Why do you think he reacted that way?” Be prepared to act as a sounding board.
10. They Will Attract the Spotlight
Entrepreneurs naturally attract attention, which can be frustrating if you feel sidelined. It is vital for the entrepreneur to intentionally share the spotlight with their partner, recognizing that they would never be where they are without that foundational support at home.
11. Your Friends and Family Won’t Understand
Only about 14% of American workers are entrepreneurs. This means 86% of the population has zero idea what it takes to build a business. When your family tells you, “He works too hard,” or “She should be home by 5:00,” they are judging an entrepreneur through a 9-to-5 lens. Only take relationship advice from people who have actually survived building an empire.
12. They Have Exceptionally Strong Opinions
No one dedicates their entire life to a single, highly risky vision without having strong convictions. Because of this, they will likely have very strong opinions on politics, the economy, and business.
13. They Despise Lazy People
Entrepreneurs can read through BS instantly, and they have zero tolerance for laziness. They want a partner who is also in the hunt, someone who is growing, learning, and striving for something meaningful.
14. They Are Frequent Travelers
If they are building a national or global brand, they are going to be on the road constantly meeting with vendors, investors, and clients. You must figure out how to build your own identity and entertain yourself while they are gone.
15. They Get Bored Very Quickly
To keep up with an entrepreneur, you must be spontaneous, curious, and constantly growing. If you stagnate, the relationship will stagnate.
The Partner’s Perspective: How to Thrive Together
(Insights from Jennifer Bet-David, wife of Patrick Bet-David)
If you are the one dating or married to the entrepreneur, here is how you actively survive and support the journey:
- Be Patient: When they are late, remember they are likely on a call that will eventually fund your future vacations and lifestyle.
- Praise Them Privately, Critique Them Privately: Never air your dirty laundry or argue in front of friends. (Read Love & Respect).
- Build Your Own Identity: Commit heavily to your own personal development. Take classes, learn to ski, read books, and don’t wait around for them to entertain you.
- Be a Uniter, Not a Divider: When they come home furious at an employee or a partner, try to help them see the other perspective rather than fueling their rage.
- Immerse Yourself: Learn about their business. If you undermine their passion, it will create a natural divide that will destroy the relationship.
A Message Directly to the Entrepreneur
If you want your partner to support your crazy dreams, you must uphold your end of the bargain:
- Produce Results: The struggle cannot last forever. You have to eventually go out there and actually make money.
- Actually Work When You Are Away: Your partner is sacrificing time with you. Be productive, not just “busy.”
- Protect Their Trust: Trust is like a credit score. Don’t do things that cause massive defaults.
- Involve Them: Talk to them. Tell them about the business. Do not shut out the person who is holding down the fort while you conquer the world.
Dating an entrepreneur requires massive initial sacrifice, but if you do it right, the long-term fruits of the labor are unparalleled.
Here’s a podcast with my wife and I on what we learned in our dating experience
