Entrepreneur Dating Guide: How to Find Love While You Chase Your Passion

Cover Image from "Entrepreneur Dating Guide: How to Find Love While You Chase Your Passion |  Natfluence Article

Entrepreneur Dating Guide: Overview

This guide focuses on entrepreneur dating advice. These strategies also apply to anyone with a career-focused lifestyle – or those who feel they are “too busy to date” – you know who you are.

This dating guide is not about getting more dates, it’s about being smart with your time so you can find the right romantic partner.

Drawing upon dating tips from top dating coaches, expert matchmakers, and relationship experts, the Natfluence Entrepreneur Dating Guide breaks down the challenges of dating as they apply to an entrepreneur lifestyle.

The guide then offers 10 actionable dating tips to enhance your dating life so you can experience a happier, more successful journey meeting (and keeping) compatible partners.

This dating guide was compiled using research studies, dating statistics, and expert interviews from:

  • JoAnn Ward — Founder of Master Matchmakers | Former Host of VH1’s Tough Love
  • Barbie Adler — Founder of Selective Search | National Dating & Relationships Expert
  • Hayley Quinn — UK’s leading Dating Expert & Coach | TED Talk Star
  • Angela N. Holton — Founder of Love Sanctuary | Dating & Relationship Expert
  • April Davis — Founder of LUMA Luxury Matchmaking | INC. 5000 Entrepreneur
  • Scott Valdez — Founder & CEO of VIDA Select
  • Jaime Bronstein — Host of “Love Talk Live” | #1 Rated Relationship Coach by YahooFinance


Entrepreneur Dating – Buckle Up

Starting Point: Acknowledging the value of a romantic relationship

True entrepreneurial success isn’t just about making money. It’s about building a business that allows you to have freedom. Freedom to live the life you want and to enjoy the things that make you happy – with the people you love.

Image of Heart and Note | from "Entrepreneur Dating Guide: How to Find Love While You Chase Your Passion |  Natfluence Article

While happiness is different for everyone, one thing is the same in both the business world and in personal life: The right partnership will make you stronger and help you get what you want.

This is particularly relevant for entrepreneurs where the line between work life and personal life is blurry.

So, if entrepreneurs and busy professionals quickly understand the value of a business relationship and they excel at navigating those waters, why is it that there is more turbulence when it comes to romantic relationships?

Well, for one it takes work to find the right romantic partner. And, we all know that more work means more time.

So before reading any further, take note that this dating guide is geared toward those that actually want a long-term romantic relationship. It provides guidance on how to approach dating as an entrepreneur or busy professional.

Why Is Dating So Hard – 3 Barriers to Dating

Putting things in perspective:

Before diving into how to take control of your dating life, let’s put things in perspective.

Dating is difficult no matter who you are.

You might think that it should be easier to meet a romantic partner with all the dating apps and dating services. But, that’s not necessarily true.

According to most Americans, the dating game has gotten harder in the 21st century. A Pew Research study revealed that nearly half of Americans say that dating is harder now than it was 10 years ago.

To help understand why let’s have a look at three dating challenges:

  1. Information Overload & The Paradox of Choice
  2. Time & Effort
  3. Unrealistic Expectations & Mindset
Image of "Dating is Hard" Infographic | From Entrepreneur Dating Guide by Natfluence

Information Overload / The Paradox of Choice

Technology has infinitely expanded the pool of potential daters and has created somewhat of a “dating buffet” to choose from. Between dating apps, social media, and the ever-growing list of dating services, the options can be overwhelming.

There are over 1,500 dating apps and websites out there with more than 44.2 million users of online dating services in the U.S. alone. It’s estimated that this will increase to 53.3 million by 2025.

The larger variety and volume of potential matches increases the ability to meet more people, but reduces the chances of meeting a quality match. Here’s why.

  • Not Enough Action – Too many options can lead to “paralysis by analysis.” In his book, “The Paradox of Choice: Why More is Less,” Barry Schwartz a Professor of Social Theory and Social Action in the psychology department at Swarthmore College, explains that choice overload can cause stagnation, or failure to move forward.

According to Schwartz, too many options will make you question your decisions before you even make them. This results in unrealistically high expectations, and can make you blame yourself for any failures.

  • Too Much Action – On the flip side, there is the “Swiping” or “Shopping” phenomenon, whereby people will impulsively swipe right or rack up their options without much thought, thereby dehumanizing the process of dating.

This enhances the quantity of encounters or interactions but may lead to a “depersonalization” effect where dating becomes more impersonal. In this instance, too many choices lead people to either “look for the next best thing” or move on too quickly without giving enough attention to someone that might otherwise be a strong fit as a long-term romantic partner.   

Time & Effort

The amount of time that dating takes can be a huge deterrent. And, for those that put in the time and don’t get the desired results, it can feel hopeless.

Based on a study conducted by Badoo, Millennials spend more than 10 hours a week (90 minutes a day) just on dating apps: men spend 85 minutes a day swiping on apps while women spend 79 minutes a day swiping.

Image of Dating is Time Consuming | From Duke University
Source: ModernGentlemen

Duke University found that it takes 5.2 hours a week looking at profiles and another 6.7 hours sending and replying to emails or messages to get just 1.8 hours of average dating time in real life.

This doesn’t include the full amount of time that daters actually spend on real life dates.

The amount of time spent on dating efforts coupled with the mental energy that goes into dating can feel exhausting.

Not to mention, those with full-time jobs (particularly in the U.S.) are super busy to begin with. According to the U.S. BUREAU OF LABOR STATISTICS, the U.S. is the Most Overworked Developed Nation in the World whereby full-time employed females in the U.S. work an average of 8.33 hours per day, while full-time employed males work an average of 9.09 hours per day.

Mindset & Expectations

With the larger pool of options accompanied by advances in technology, it’s hard to calibrate expectations and put things in perspective. Many daters are either overly optimistic when they go on a first date, or they are pessimistic. Both mindsets often lead to disappointment.

To make things worse, there is a lot of pressure to meet someone, both internally and externally:

Inward Pressure

Going back to “The Paradox of Choice,” Barry Schwartz explains that having too many options results in unrealistically high expectations because with more choices, people expect greater satisfaction. Thus, in instances where people don’t get what they want they tend to blame themselves. This can result in lower self-esteem and higher anxiety.

Outward Pressure

According to Statista, Americans Spend more than 2 hours a day on social media. What does this have to do with dating and relationships?

Source: Pew Research

A lot. People aren’t posting about the bad times in their relationship; they are giving you the highlights. You are seeing what people want you to see. This can give the illusion that everyone but you is in a happy relationship.

In fact, 33% of social media users who are single have reported that seeing relationship posts make them feel worse about their dating life.

Why Is It So Difficult to Date as An Entrepreneur?

In addition to the general dating challenges that apply to everyone (mentioned above), entrepreneurs and busy professionals may have additional considerations due to their lifestyle.

  1. Emotional Constraints
  2. Time Constraints
  3. Erratic Schedules
  4. Financial pressure

These factors not only make it difficult to date but can also make it hard to continue an existing relationship.

Image of Why Is It So Difficult to Date as An Entrepreneur? | Infographic | From Natfluence Entrepreneur Dating Guide

Emotional Constraints

The entrepreneur’s lifestyle is often associated with a rollercoaster of emotions, including uncertainty, the need to always be ‘on the clock,’ intense passion, and enhanced pressure to succeed.

When it comes to a romantic relationship, April Davis, the founder and president of LUMA Luxury Matchmaking, says “[e]ntrepreneurs have a difficult time dating because they’re already in a relationship. A relationship with their business.

Davis explains that “[i]t will be challenging for anyone to become a bigger priority than the entrepreneur’s business.”

Image of April Davis, Matchmaker | Founder & President of LUMA Luxury Matchmaking | From Natfluence Entrepreneur Dating Guide
Quote from Natfluence Interview with April Davis | Photo courtesy of LUMA –Luxury Matchmaking

Tweet This

Although this doesn’t mean that an entrepreneurs can’t have more than one priority, it is not surprising that entrepreneurs may prioritize their work over their romantic life. This may have to do with the fact that they feel accountable for their own success, thereby increasing their pressure to perform.

Most entrepreneurs view their business as their “baby.” They feel an obligation to stay focused on growing it until it can generate a certain amount of money on its own. With that comes a strong sense of passion, but also stress.

The following statistics provide some insight into the entrepreneurial mindset;

  • 63% of entrepreneurs start their own business for reasons other than money (e.g., freedom, control, autonomy, quality of life)
  • Two-thirds of entrepreneurs started their business so they could build something from the ground up.

The freedom and passion that comes with entrepreneurship is invigorating. But the responsibility that follows may also increase stress. According to the Gallup Wellbeing Index, almost 50% of entrepreneurs in the United States report being stressed.

Stress is not a good thing for dating or relationships. It has a tendency to pull out people’s worst traits, including becoming withdrawn, distracted, and less affectionate

Time Constraints

Entrepreneurs can often be pulled toward a workaholic lifestyle with lack of a work/life balance, especially in the beginning stages of setting up a business when the pressure is on to succeed.

A New York Enterprise Report found that those who are in charge of their own business work twice as much as regular employees. It also found that 33% of small business owners reported working more than 50 hours per week, and 25% said they work more than 60 hours a week.

Another study by Gallup shows that 39% of startup founders and entrepreneurs in charge of their own company work over 60 hours a week.

Source: Score.org

According to a study from OnDeck, only 57% of entrepreneurs take vacations, and when they do, it falls short of 2 weeks per year. Of the 57% that do take vacations, 67% of them will work at some point during their vacation.

The “To Do” list of an entrepreneur can feel never-ending. One day you’re seeking angel funding and building your MVP, and the next day, you’re putting together a digital marketing plan.

As you push off dating to another day and another day, you find yourself never prioritizing romantic partnerships.

Again, having less time does not mean that entrepreneurs can’t date, but it makes it more challenging and means they need to use their time more wisely.

Erratic Schedules

Another factor that can complicate things is the relative instability and unpredictability of an entrepreneur’s lifestyle, compared to someone with a 9-5 job. There is no roadmap when it comes to entrepreneurship. It doesn’t matter how disciplined or organized you are.

Part of being an entrepreneur means being flexible and changing direction at a moment’s notice. If an unexpected opportunity arises, you need to go for it.

As a result, while you can surely maintain a general routine and plan for your days, there will always be an element of uncertainty that goes above and beyond what you would expect from the 9-5’er.

This could be hard when it comes to dating, particularly in the early stages.

To give you an idea, here’s an example of a day in the life of an entrepreneur, courtesy of Karin Bohn:

Video: Examples of entrepreneurs’ busy schedule

Financial pressure

Dating is expensive.

Based on a survey of 1,000 Americans ages 18-40, millennials spend an average of $69 on just the first date. For those between the ages of 25-40, 28% spend at least $100 on a first date, and a third of them spend $250 or more per month on dating.

According to research conducted by Elite Singles, date nights in American cities costs an average of $116 in for basic things such as a mid-range dinner for two, a shared bottle of wine, one pre or post-dinner event (such as a movie or drink spot), and transportation. For those in New York City or San Francisco, these prices rise to approximately $140.

Image of Cost of Date Night Chart | Example of Dating is Expensive | From Natfluence Entrepreneur Dating Guide
Source: Elite Singles

For the average entrepreneur in the beginning stages of their venture, these costs can add up pretty quickly.

The amount of money that entrepreneurs make depends on many factors, including their industry, what stage their in and their location, but as a baseline, a study performed by Zippia, a career information website, estimated that the average Entrepreneur makes $86,943 in the United States, where by the average hourly pay for an Entrepreneur is $41.8, and the average entry-level Entrepreneur salary is $61,000.

But there’s one other consideration at play.

More important than what an entrepreneur makes and their ability to spend is their “willingness” to spend.

Entrepreneurs are likely to consider dating a “luxury” item in the beginning stages of their venture. With their mind focused heavily on their business, the majority of their spending is likely allocated to their business mission. This may make it more challenging for entrepreneurs to justify the high costs of dating.

The Most Common Dating Mistake Made by Entrepreneurs

Due to the barriers mentioned above, it’s not surprising that entrepreneurs may view dating challenges as an excuse to put off dating until later and throw themselves into their work, thereby cutting themselves off emotionally and leading to an unbalanced work/life balance.

“A common misconception by entrepreneurs is that they will get around to the “love thing” once this funding round is complete or once the new website is live or once the product is finished,” explains Hayley Quinn, the UK’s leading dating expert.

Image of Hayley Quinn | Dating Expert & Coach | From Natfluence Entrepreneur Dating Guide
Quote from Natfluence Interview with Hayley Quinn | Photo courtesy of Hayley Quinn

Tweet This

After all, if you’re waiting for the “perfect” moment to start your search for love, there will always be something else that needs to be completed first.

Barbie Adler, Founder of Selective Search, sees countless clients and has a similar observation. She notices that top-tier executives have a tendency to put their personal lives on the backburner, and end up feeling lonely at the end of the day. She encourages them to put themselves out there if they have the desire to date.

Image of Barbie Adler | Founder of Selective Search | From Natfluence Entrepreneur Dating Guide | Common Dating Mistake Made by Entrepreneurs
Quote from Natfluence Interview with Barbie Adler | Photo courtesy of Selective Search

Another common tendency is that entrepreneurs may go on dates but either not open up fully or give up too quickly.

Based on a series of Natfluence Interviews with dating experts and relationship coaches, the tendency to postpone dating or withhold emotionally is often due to the fear of being taken off course or a limiting belief that a busy lifestyle is the reason why they are not finding the right person.

Dating & Relationship Expert, Angela N. Holton, explains that dating is hard for everyone, but it’s easier for entrepreneurs to point to their lifestyle as an excuse for not having time to date or not finding the right partner.

Holton’s view is that “These are all limiting beliefs that need to be debunked. You get to create, or at least try to create, the life you deeply desire. What gets in our way is our own thinking. We need a radical shift to our mindset.”

Image of Angela N. Holton | Founder of Love Sanctuary | From Natfluence Entrepreneur Dating Guide | Common Dating Mistake Made by Entrepreneurs
Quote from Natfluence Interview with Angela N. Holton | Photo courtesy of Angela Holton

Tweet This

Similarly, Scot Valdez says “I think plenty of people use their busy lifestyle as an excuse for why they haven’t found a good relationship. For entrepreneurs especially, the struggle is real, because your business is everything. But using your dedication to your company as an excuse for being single when you don’t want to be single is absolutely limiting. For there to be growth, there needs to be change.” – Scott Valdez.

Entrepreneur Dating Advice: 10 Actionable Tips for How to Date When You’re Busy

This section focuses on providing actionable dating tips and strategies for overcoming the following four challenges, all while taking specific steps towards a healthier and more enjoyable dating life that can work in conjunction with a busy lifestyle:

  1. Emotional Constraints
  2. Time Constraints
  3. Erratic Schedules
  4. Financial Pressure

1. Calibrate Your Mindset

When it comes to dating, your mindset is the first and most important factor.

Dating (like building a business) is a journey. Along the way, you will have to make an infinite number of choices. There will be countless ups and downs. Assumptions you believe to be true will end up being false. People will give you conflicting advice.

At the end of the day, you are responsible for your own roadmap.

This requires:

  1. Confidence;
  2. Persistence;
  3. Strategy
  4. Flexibility

You need to believe that you will get what you want, and stay the course – all the while taking decisive action towards your goal and being open to pivoting where necessary.

In addition, it’s important to enjoy the journey and do things that make you happy. People who are in a happy state of mind, tend to have more positive thoughts, and vice versa.

This is particularly relevant when it comes to dating because your mindset impacts how you feel and the energy you give off – both of which play a significant role in attracting and keeping a romantic partner.

Of course, changing the way you think is easier said than done, but with the proper planning (see next section) and the dating tips in this guide, you can chip away at those barriers and adopt a more productive approach and openness to dating.

2. Date Like it’s Your Business – Develop a Dating Plan & Strategy

Most entrepreneurs would not pursue a new business idea without a solid business plan.

There’s a reason why developing a business plan is the first step in starting a business. And, it’s more than a clerical exercise.

A strong plan forces you to think through and define your approach. It ensures that you have a direction and makes it easier to get clear on what you are trying to achieve. Most importantly, if done correctly, a plan holds you accountable for taking action and moving closer to your goal. It serves as a navigation system that will help you to get meaningful answers and remain focused on what’s important.

Most entrepreneurs love putting together a plan.

Why? Because a well-thought-out plan puts them in the driver’s seat and reveals a clear path.

So, if you want to find success in your dating life, approach dating with the same discipline, vigor and passion as your business.

Try documenting the following:

  1. Mission Statement — Define your dating goals and objectives
  2. Executive Summary — Articulate what makes you unique and desirable
  3. Budget & Time — Identify how much money and time you are willing to commit to dating
  4. Marketing Strategy — Outline how you will present your best self
  5. Execution Strategy — Determine the key actions that will help you achieve your dating goals, while minimizing cost and time.

3. Get a Dating MBA

Most people do not take the time to educate themselves on dating.

Here are three reasons why:

  1. Not sure where to start; or
  2. Don’t really think about it; or
  3. Think it’s silly

Either way, this gives entrepreneurs an advantage. Entrepreneurs tend to be lifetime learners. They crave knowledge, and as long as something has value, they will educate themselves on the topic and identify how to take action on what they learn. Those who take the time to learn what others don’t, get ahead faster.

When it comes to dating, consider the following as learning opportunities:

  • Researching the dating apps and platforms that work best for you
  • Working with what you have to present the best version of yourself
  • Paying more attention to how you spend money on date-related activities
  • Optimizing your dating photos and profiles
  • Finding better romantic matches with long-term potential
  • Identifying blind spots and limited beliefs about yourself and dating
  • Differentiating yourself from the crowd and getting noticed
  • Building confidence and attracting more matches

As with any form of learning and education, there is rarely a single source that will provide all the answers. Instead, it’s about the cumulative knowledge and experience that you gain through different perspectives, including trial and error.

Here are your Dating MBA tools:

Dating books – There are a plethora of dating books out there, and the ones that will have the most benefit for you will depend on your specific needs. However, a strong starting point is to choose 3 books that cover a range of relevant topics, such as positive thinking, communication, and actionable dating suggestion.

It’s important to scan the table of contents, read the reviews and ensure there are a lot of top ratings. If you hear of a good book through word of mouth, or if you already know of a trusted and credible expert in the field of dating and relationships that has a book, it’s worth exploring.

Dating Blogs – Identify three dating blogs from credible dating experts that speak to you, and then sign up for their newsletter. This will ensure that you are getting regular tips and updates that you can use to keep inspired and enhance your dating game.

When identifying a blog to follow, it helps to look at their press page to see what independent sources are saying. Also have a look to see what types of industry insights the expert is putting out there. Are they speaking at conferences, giving TED Talks, featured on Television, publishing books? Do they have a large following?

Dating Courses, Workshops & Seminars – Try attending one dating course for fun. Sure, this will probably solicit the most resistance because you are putting it out there that you are looking for help, but hey, try to get over it.

Getting outside your comfort zone is healthy, and you never know who you will meet at these events. Not only are you likely to learn something new, but you will hear from other people in the same situation as yourself. If you are not ready for an in-person learning event, there are also online alternatives. Try both to get the most benefit.

Dating Coaches – Most successful entrepreneurs have either a business coach, a business mentor, or a board of directors. This is to ensure that they are receiving support in the form of regular feedback and guidance. No one person knows everything – not even about themselves.

Similar to dating workshops and seminars, dating coaches focus on topics such as mindset, confidence, communication, and opening the door to more opportunities. However, the methods are tailored to the individual and often involve role-playing, behavior modelling, regular discussions or other strategies to help clients meet and attract romantic partners.

The benefit of a dating coach is that over time, they are able to spot patterns, tendencies and biases that you might not be aware of. They can then offer personalized and independent recommendations based on their professional judgement and experience.

Check out what Joanne Ward has to say about Dating Coaches here:

4. Create a Compelling Pitch Deck / Media Kit

When entrepreneurs are looking to attract investors or explain what their business does, they often have both a pitch deck and a media kit. Both are geared towards explaining the mission and appeal of their brand – albeit in different ways. The goal is to be concise and factual while highlighting the key benefits and value of the company.

The same holds true in dating. You want to be authentic, but you also need to clearly and succinctly explain what you’re about, what you’re looking for and what makes you unique – in an engaging way.

Because this is your dating life, it’s important to have fun. But, it’s also important to create a strong and accurate representation of yourself that can quickly and effectively speak to your persona (who you are and what a partnership with you would look like).

This can be achieved through up-front planning for the content that you use in your dating efforts — such as for online dating profiles, where you portray yourself using writing and visuals (e.g., images, video, voice).

It requires a time investment in the beginning, but with the proper planning, you can create an invaluable asset that can be used to save you time, money and energy down the road.

We break this down in more detail in the following two sections.

5. Choose Your Words Carefully

Writing is hard. It’s even harder to write about yourself. Therefore, it’s no surprise that this is where most people struggle and tend to put in the bare minimum to get it done. However, the words you choose (and how you use them) is what will differentiate you and drive your subsequent interactions.

This is an opportunity for those that do in fact put in the work. This is where you can surge past your competition.

Start with these eight steps to help get ahead of the curve:

1) Provide Meaningful information – You should by no means tell your life story, but as mentioned above, there should be enough detail for someone to get a sense of your character and interests. Having the right information will work in your favor and help to attract stronger matches for you.

In determining what details to include, focus on what’s most important to you – both in a person and in a relationship. You can then use the tips below and in the rest of this guide to figure out the best way to communicate those details.

2) Give enough detail, but not too much – The idea is to keep things brief while conveying meaningful information. Start with an offline draft of what you want to say. Just write. Any length is fine.

Then, review what you have to make sure you captured the essence of the most important points. Next, copyedit your work and cut it down so that it conveys the same points with fewer words. The shorter the better.

3) Build Trust – The easiest way to build trust with your words is to: a. Avoid making claims or statements that come across as disingenuous; b. Include details about yourself that demonstrate you are not afraid to open up; c. Write something that elicits a positive response, such as a smile or chuckle; and d. Show that you have genuine intentions by taking the process seriously (e.g., put thought and care into what you write).

Of course, this is not enough on its own to solidify trust but you surely don’t want to immediately lose trust because of what you write (or don’t write). You need to establish a baseline that you can build off of.

4) Include something memorable / catchy – Try your best to make sure there is something in your profile that grabs attention and makes your audience want to learn more about you – or better yet, meet you. That could be humor, wit, a special talent, or anything else that comes across as new and interesting.

Think outside of the box and do something that others aren’t doing. It doesn’t even have to be what you say. It can be how you communicate it. Get creative, and pique curiosity.

5) Keep an open-door policy – It’s very hard to “cold call” people. Reaching out to strangers can be awkward, especially if you’re not sure what to say. Make it easier by being approachable. You can do this by including a prompt or question in your profile that illicit a positive response and encourages people to connect with you.

Even better, you can use this an opportunity to attract better matches by designing your prompt or question to around your interest or character. For instance, if you are looking for a partner that loves travel, you can include something along the lines of “As an avid traveler, I love exploring new places, and I can’t wait for my upcoming trip to Paris. Any suggestions?”

6) Avoid being negative – Tone is important and provides an immediate message.

For anything negative that you want to say, there is a positive way to frame it. Do that instead. Most people are looking for a partner to bring them up not down.

7) Don’t skimp on grammar – Sure, in this day and age grammar and spelling might not be as important, but when you have very little information to work with, every detail counts.

If anything, proper grammar shows that you care.

8) Elaborate on what it means to be an entrepreneur – Being an entrepreneur is exciting and wonderful, but not everyone understands what it means to be an entrepreneur so be mindful of how you describe your occupation.

For instance, using the term “entrepreneur,” alone might not do you justice. It helps to provide additional specifics as to what you are working on so that others get share in the excitement and get a better understanding of what your day to day life looks like.

6. Treat Your Visuals as a Team

A picture is worth a thousand words, and when it comes to first impressions, you have a limited window to get your message across. Fortunately, by combining words with images, you can craft a powerful message that can be conveyed quickly.

In the dating arena, it’s tempting to pick the top five or so photos of yourself where you think you look the best, and call it a day. This is a mistake.

Every picture is an opportunity for you to message something important. Your visuals should work together to reflect a larger picture. This is your chance to tackle important details that you weren’t able to capture with your words. Every image should say something new.

Here are seven tips for enhancing your dating photos:

1) Include a clear headshot photo – Make sure that you have at least one photo that shows a close up of your face. In most cases, this would be your primary photo.

Photos where you are making direct eye contact and smiling tend to perform better as they convey a sense of trust and confidence. Having a close up (but not too close) is more personal and shows that you are not “hiding” anything – as opposed to photos where you are far away.

2) Include an action shot – Include one photo that shows you doing one of your favorite activities. This not only helps to give people a sense of what you are interested in, but it demonstrates that you are active and enjoying life.

This could be something that you and your future partner could be doing together. It helps for others to visualize what life would be like with you.

3) Be mindful of social shots – Providing a picture of yourself in a social setting can certainly add color to what it would be like to date you, but they may also work against you. Ideally, these types of images should serve as social proof that you are likeable and people enjoy being around you. They may also provide a glimpse into your social circles and who you spend time with – or so people will assume. Social shots can be tricky.

Firstly, you want to make sure that whoever is in your photo is OK with being included. Next, you should pick a photo where you are the focal point – all eyes on you. It doesn’t help you to include a photo where you are being drowned out or outshined by others. If the photo isn’t helping you, it’s hurting you.

Also, pay attention to what you are doing in the photo. What message do your actions convey? A strong social shot should work in your favor, and highlight why your friends love and trust you. A stranger should be able to look at the photo, and think “wow, I would really have a blast with this person – but I would also trust them with my dog.”

4) Establish credibility and trust in your photos – Your photos should provide a well-rounded and natural representation of who you are. This means including a wide enough variety of images that provide accurate clips of your life.

Your images should be recent and also include one clear face shot and one full body (head to toe image) so that when your potential partner visualizes you it will match up as closely as possible when they eventually meet you. Other tips for building trust include going easy on the filters and avoiding poor-quality photos – such as images that are grainy, dark, too far away, too close for comfort, blurry or not showing your face.

5) Leverage professionals – There is absolutely nothing wrong with getting help. That doesn’t mean hiring a photoshop editor to make you look like a fashion model. It means teaming up with an expert to help provide guidance and/or assist you with creating high quality photos that tell your story and reflect what you look like. Photos, like mirrors, can be deceiving.

There are many factors to consider; lighting, angles, shadows, distance, pose position, body posture, background, time of day, eye contact, etc. Keep in mind that the intent is to get help with showing your best self, not to show a different person.

If all your photos are professionally taken glam shots, it will work against you. Focus on building a balanced set of photos that speak to your different character traits and attributes, while being as informative and natural as possible.

6) Get sufficient feedback – There are two common mistakes when it comes to getting feedback on dating photos: 1. Not getting enough feedback; and 2. Getting biased feedback. The worst mistake, is to not get any feedback at all.

First, it’s important to acknowledge that your friends and family are biased. They already have a deeply ingrained view of you, and are not able to provide objective advice in the context of a potential romantic partner. If you are going to ask friends and family for their input, get several people (the more the better) to rank their favorite photos.

Next, you need to get independent, unbiased feedback from people that do not know you, and who do not have any vested interest. This combination of objective feedback coupled with a statically significant sample will take the guesswork out which photos to use and will save you a ton of time.

7) Align your images with your words – This may seem obvious, but it is still overlooked more often then it should. Make sure that your photos are consistent with what you write. This consistency will provide for a stronger overall image of you, and help to build credibility.

If you are telling the world that you are energetic and fun, then your images should show you being active and doing interesting things.

7. Put Yourself Out There, and Take Your Chances

So what does it mean to put yourself out there?

In the book “Hustle,” Neil Patel, points to Dr. Dean Keith Simonton’s work in explaining that the most successful people are not the ones with the best batting averages, but rather those that get up to bat the most.

His point is that you have a higher probably of success when you take more chances.

Patel goes on to explain that not only does this increase your odds of success but that you do not need to worry so much about failing because doing the wrong thing assists in telling you what the RIGHT THING is.

This alleviates some of the fear associated with “striking out” or getting hurt. 

But, there is a bit more to it. Getting out there and taking a chance doesn’t mean blindly throwing darts at a dartboard. Rather, it means decisive movement toward a goal, however indirect, by which the motion itself manufactures luck, surfaces hidden opportunities, and generates momentum.

Savvy business folks know this all too well, which is why they are out in the world networking, cold calling and marketing their business at every opportunity they get –  across multiple channels.

The same applies to your dating life. Putting yourself out there means not being afraid to let the world know who you are, and that you are open to new relationships. Beyond that, it means keeping your head up, your eyes open, and seizing opportunities through decisive movement towards your dating goals. Opportunity presents itself in every conversation and interaction. By spotting and pursuing opportunities in your everyday life, you can “manufacture your own luck.” 

Here are some examples of putting yourself out there:

Leverage multiple dating apps and websites – You don’t want to pick too many, but pick a few different apps or sites that target different audiences and give them quality attention. If you are using more than five online sources and recycling the same information and photos, and not giving them proper attention, then you are wasting your time.

Pick the best three or so online sites that align with your dating objectives, and then tailor your information to the site and your audience.

Ask your friends and family to set you up – Sure this may be awkward, but get over it. Who do you think startup founders go to for their first round of funding? If you think asking your friends to introduce you to a new love interest is uncomfortable, try asking them for money.

At the end of the day, it doesn’t matter what you are asking for, just ASK. Your friends and family are a strong support network. They know you, they trust you, and they have your best interest in mind.

Get started today. Let your circle know that you’re single and interested in being invited to events where you can mix and mingle with others. Once it’s out there, new opportunities will come your way.

Embrace “Hidden opportunities” – This refers to finding indirect success. The world is not linear, it works in mysterious ways. If you remain open to attracting opportunity, you’ll be amazed at what you find. You can attract opportunity simply by starting up conversations and increasing the number of interactions during the normal course of the day.

Be open and friendly with new people and engage in genuine conversation. You never know where it will lead. Get out there and let the universe work its magic for you. If you don’t do anything, nothing will happen.

Practice Getting Comfortable with Failure – No one likes rejection. But you can build up a healthy resilience that will allow you to take more risks. The key word here is “healthy.” In small intentional doses failure can make you stronger and smarter.

45% of new businesses fail within the first five years and about 90% of startups fail eventually. These are extremely daunting statistics – but do they stop entrepreneurs from trying? No.

Entrepreneurs understand that failing is part of the  process, not a loss. Failure is merely a pit stop on the road to success.

So what’s the difference when it comes to dating?

It feels more personal to be rejected as a person rather than a business. But, it’s not as personal as you might think. After all, how offended should we be to get turned down by someone we’ve met for five minutes?

Be proactive in approaching romantic interests.  Don’t wait for the perfect moment or even validation that they are interested in you. If you’re gut tells you to reach out, send that message or strike up that conversation. If it doesn’t go anywhere, move on. Rinse and repeat.

Leverage the love professionals – Matchmakers and dating coaches live and breathe to help people win in the game of love. Their brains have a built-in microchip that continuously scans and rechecks their internal rolodex of love for potential matches.

Their win is your win, and they are passionate about it. More often than not, they have a new perspective to offer. Better yet, they have access to a new pool of potential love interests that want the same thing as you.

As an added benefit, matchmakers and coaches offer a variety of tools and services above and beyond matching you with other people. This can be used as an educational opportunity to strengthen your dating game. Like anything else, opening the door to relationship experts may work or it may not, but’s it’s worth a shot.

Having a credible source in your corner working for you keeps the momentum going and can save you valuable time. At the very least, you will learn something new and get on dates.

8. Invest Your Time Wisely, and Cut Your Losses.

In the previous tip, we talked about the importance of getting out there and tacking chances. You need to do that. However, there’s a catch.

As a busy entrepreneur, you need to invest your time wisely. Being proactive in the dating game doesn’t mean swinging at every single pitch. It means getting up to the plate as often as possible and swinging at the pitches that you think you might be good for you.

You need to trust your instinct.

This is why savvy entrepreneurs know that they have to cold call and reach out to as many potential investors as possible. But it is not a blind strategy. There is often a list, and that list was put together based on a variety of relevant factors including research and personal recommendations.

From a dating perspective, investing your time wisely involves making smart decisions, trusting your instinct and creating healthy rules for yourself.

If certain dating decisions are not bringing you closer to your goal and are not rewarding learning experiences, then that’s time that could be allocated elsewhere.

Here are four tips for how to not waste your time:

  • Define your dating goals and align your approach with your goals. One way to do this is to optimize your dating profile to: 1. filter out what you don’t want; and 2. attract what you do want (this narrows down the pool to those who are a better fit for you).
  • Limit the amount of time you spend on pre-date communications. Focus on getting on the first date so that you can see if there is ‘in-person chemistry’ as early as possible.
  • Do not force a second or third date – Do not continue dating or pursuing someone because you are lonely or because you enjoy the attention. It can be easy to continue dating someone out of comfort – especially if you are busy and little effort is required. Don’t do it. Life is too short. The moment you realize things will not evolve into anything meaningful, cut your losses. Respect your time, and move on. You will find something that is a better fit for you – and it’s the right thing for the other person.
  • Focus on meaningful traits and long-term potential – Since this dating guide is about finding a partner that will enrich your life, one of the most important things to focus on is long-term potential. That means paying attention to the bigger things that may play a larger role as the relationship goes on. This includes aligning on core values, how a future looks together, and overall compatibility. It’s important to address these items as early on as possible.

9. Cultivate and Trust Your Instinct

Your instinct is the most valuable tool you have.

It’s a built-in personal navigation system, and it’s at work 24/7. With every decision or choice, it’s churning away in the background whether you like it or not. Unfortunately, over time we’ve learned to ignore it as background noise when we don’t like what it’s telling us.

Jen Sincero explains it like this:

“We’re born knowing how to trust our instincts, how to breathe deeply, how to eat when we’re hungry, how to not care about what anyone thinks…Then, as we grow and learn from the people around us, we replace many of these primal understandings with negative false beliefs, fears, shame, and self-doubt…and, instead of following our instincts and our hearts, we invest in what other people believe…”

Jen Sincero – #1 New York Times Bestselling Author of You Are a Badass

Sincero’s point is that what was once one of our most valuable assets for making decisions has been slowly decommissioned and replaced with outside sources. As we grow older and become more socialized, we trust our intuition less and look to external validation in our friends, families and even people we haven’t met.

So what’s the solution?

First: Awareness. Second: Practice.

We can tap back into the power of our intuition by relearning how to use it. Like training a muscle, we can get better at trusting our instinct and eventually use it more.

Step 1: Awareness. This involves identifying when your instinct is telling you something. And then, becoming more ‘in tune‘ and familiar with that feeling. Think about all the times that you have said “I knew I should have listened to my gut.” That feeling in your gut is your instinct speaking to you. Sometimes, it even comes across as a tingling feeling.

Still not sure?

Try this trick: Next time you are stuck on making a decision, narrow it down to two options. Find a coin, and assign those options as heads or tails. Next flip that coin and let it land on your hand. Before looking at whether its heads or tails, ask yourself this question before you have time to think any further about it: what do you want it to be?

Whatever the first answer that came to your mind (before you started rationalizing it away) is likely what your intuition is telling you to do. Of course, you might have to rephrase that question depending on your situation, but you get the idea.

Step 2: Practice. Once you are aware of what listening to your intuition feels like, you can sharpen this awareness and strengthen you’re ability to identify and summon it. Here’s how to practice: next time you are stuck on making a decision, catch yourself. Don’t ask anyone for help. Instead, go to a quiet space, think through the situation, and think about what you would normally ask a friend. Take each questions one by one, and consult with yourself.

Do not overthink the responses.

Just pretend that you are talking to someone else, or just say the first thing that comes to mind. Now, this is the important part: Recognize the feeling that you get in your gut as you respond to each question. That is what you should focus on.

That coin toss feeling is what you can tune into for your internal guidance as you explore each of your questions. At the end of your personal Q&A session, ask yourself for your opinion on what you think you should do.

Will you get things right every time? No.

Will you feel like you made the right decision every time? Perhaps, not at first.

But, that’s OK. Often, there is no right answer. The intent is for you to get better at using your own judgement. As you get comfortable relying on your own instinct, you become more self-sufficient. Overtime, this empowers you to make faster and more effective decisions.

10. Control Early Date Spending and Alleviate Financial Pressure

Regardless of your financial situation, it’s a good idea to do some basic planning and budgeting to reduce the costs associated with dating – particularly in the beginning stages where you go on more dates with more people. By spending less on dates, you can focus more on the person and remove barriers to getting out there.

The most expensive part of dating is typically the cost of commuting, alcohol consumption and eating out.

Here are four tips for how to spend less money on dates:

1) Embrace virtual meets – Despite the excitement of an-person date with someone you have been chatting with, try a quick video chat or phone call as the next step before meeting in person. This helps to learn more about your potential date, and will also give you a better sense of what to expect. Better yet, in some cases, it may save you time and money if you decide that it’s not worth it for you to proceed with a meetup.

2) Limit your time – No need to spend so much time on a date – particularly the first date or dates where you don’t feel a spark. Many daters feel obligated to stay on a date longer than they should. This is particularly the case where alcohol or food is involved.

3) Go for creative dates over “Fancy” Dates– Try kicking things off with fun, but inexpensive ideas for the first date (or early dates). There’s no reason to go over the top the first time you meet someone. The focus should be on your conversation and interreacting with each other. Meet for coffee or a walk in the park or something else. Brainstorm a list of fun but inexpensive activities for early dates.

4) Experiment with Sober Dates – Taking this one step further, recent studies are showing that daters are more open to eliminating alcohol completely. Logan Ury, Director of Relationship Science at Hinge found that 75% of daters prefer to do something other than grab drinks on their first date.

Logan explains that daters would rather do something more creative such as meet for coffee, go for a walk, or check out a show or museum.

Reasons for this shift include the desire to be in the right state of mind while getting to know someone, as well as prioritizing physical and mental health, and saving money. In fact, 30% of daters say they prefer sober dates because they are more affordable.

Should Entrepreneurs Date Other Entrepreneurs?

One of the questions that came up more often than expected while developing the Entrepreneur Dating Guide was:

Can two entrepreneurs date?

Out of curiosity, the Natfluence team decided to scour Quora to find what everyday people were saying about two entrepreneurs dating each other, and then we asked the experts.

Here were some of the most popular and interesting responses from the general public on whether two entrepreneurs should date:

Source: Francis C.
Source: Shana R.
Source: Louis L.

We then turned to the experts.

Relationship experts on whether two entrepreneurs should date:

April Davis — Founder of LUMA Luxury Matchmaking

“It is of course possible for two entrepreneurs to date and they may very well be attracted to and respect each other. But, there are going to be some unique challenges to this relationship.

There’s a reason why many professional athletes or famous actors end up dating someone who is basically “normal”. They need someone who can be supportive of them and their profession.

The entrepreneur is usually extremely busy so finding time for two entrepreneurs to get together can be next to impossible. Usually what is more successful is when one person plays more of a supportive role and doesn’t have as crazy of a schedule or goals that require a huge amount of time and effort. They can be flexible and work around the entrepreneur’s schedule.”

Angela Holton — Dating and Relationship Expert

“Sure, why not? I think two entrepreneurs have a better understanding of one another, including their commitment to the hustle and grind, as well as a shared understanding of the capriciousness of entrepreneurship.

I believe this mutual understanding is very helpful in love and intimacy. Not everyone understands the life of an entrepreneur. Having someone who fully “gets it” can help foster a deeper connection between two partners.”

Scott Valdez — Founder of VIDA Select

“A successful relationship is all about effective communication and spending quality time together, and that’s true regardless of what you each do for a living.

As long as you’re both willing to prioritize time together and make that conscious shift out of “business mode,” two entrepreneurs can successfully date each other. However, if you are both extremely busy entrepreneurs, it may be hard to find quality time to connect at a deeper level – and that’s the kiss of death in any romantic relationship.”

Pros & Cons Overview

Here’s a convenient summary of the benefits and challenges associated with two entrepreneurs dating each other:

Image of Entrepreneur Dating Guide |  Can two entrepreneurs date? | Infographic | Pros & Cons | From Natfluence

The Verdict

Yes, two entrepreneurs can date each other. But, it comes down to three important elements:


Desire means that you must want it.

For a relationship to work, you can’t be on the fence or feel indifferent. You must want the relationship to succeed as much as you want your business to succeed. This is the level of desire that you will need because that feeling is what will be your fuel for the relationship.


Value is what you get out of the relationship: the benefits. While this is different for everyone, a general measure is that you feel happier, healthier and more successful together, rather than apart. You’re overall well-being and quality of life should be enhanced – not neutral, not lower. This means that you are getting value out of the relationship. If it’s not adding value, then it’s holding you back.


The final determinant in whether the relationship will succeed comes down to how well two entrepreneurs are able to support and elevate each other. This requires communication, empathy and compromise.

There will be times where one person will need to put the other partner’s needs above their own, and vice versa. There will also be times where priorities are in direct conflict. Therefore, it’s important to develop a system and establish an understanding to manage expectations and mitigate disappointment.

Entrepreneur Dating Advice: Final Thought

Regardless of whether you are an entrepreneur or a busy professional, dating can be hard.

The journey should indeed be fun and enjoyable, but it’s also important to spend your time wisely. It might just be the most important investment you make.

For that reason, the dating tips and advice in this guide are meant to keep you focused on what’s important to you, all the while taking action towards your goals.

You got this!


Frequently Asked Questions (FAQ)

Primary Location

Are you sure you want to manually enter your location? Have you tried typing the first few letters?

SUBMIT your location My Location is Not Listed (enter manually) clear location