Neely Steinberg Interview – Unleashing Your Inner Entrepreneur to Find Love

“Skin in the Game: Unleashing Your Inner Entrepreneur to Find Love”
Jasbina Ahluwalia interviews Neely Steinberg

A few topics Neely Steinberg addresses in this interview are:

1) (1:55)          Dating Guide for Women – Writing One

2) (7:21)          Entrepreneurial Venture into Dating

3) (10:21)        Limiting Beliefs: 5 Steps to Overcoming

4) (13:31)        Dating Board of Advisors: Who Do You Need?

5) (16:32)        Entrepreneurial Dating: Date, Learn Repeat

6) (19:02)       Ideal Partner Qualities: Top 3

7) (21:15)         Ideal Partner: 2 Mistakes Describing Them

8) (22:58)       Dating Reasonably: 3 Questions to Ask

9) (25:27)        Reflect After the Third Date

10) (31:31)      Dating: How To Improve Yourself

11) (36:27)      Dating Failures: How to Conquer Them


For the past decade, Neely has been writing and speaking about dating, love, and relationships. She has been a featured expert in a wide array of media outlets and has created and hosted two radio shows and an internet TV show on the subjects of dating, love, and relationships. Drawing from her Master’s degree in Counseling and her passion for helping others, Neely’s dating coaching practice The Love TREP®, based in Boston, is dedicated to teaching and coaching smart, educated, professional women across the world, ages 25-45, how to use an entrepreneurial spirit, mindset, and approach to find healthy, happy dating lives that lead to healthy, happy relationships.

Along her own entrepreneurial journey in love, Neely met her husband Dave. She is inspired every day by the love that she has found with him (and is especially grateful for this relationship after spending many years struggling with dating).

Concurrently to her time as a dating coach, columnist, and speaker, she has worked as an academic advisor at one of the top schools in entrepreneurship education in the country. During this time, she learned a thing or two about entrepreneurial women and men, entrepreneurship, and the ways entrepreneurs think and act when building their business ventures. She learned that people can use an entrepreneurial mindset, approach, and framework to help them create and build anything in their lives.

Being an entrepreneur in your dating and love life means investing in yourself, taking smart risks, seeking solutions to your obstacles, and enrolling others in your journey.


She has taken this collective and abundant knowledge of both the worlds of dating/relationships and entrepreneurship and spent more than a year researching and writing her first book Skin In the Game: Unleashing Your Inner Entrepreneur to Find Love, which shows women how to become entrepreneurs in their dating lives, so that they are creating, building, and shaping their love stories. Her book is not about offering generic dating advice or one-size-fits-all relationship advice; it’s about approaching the dating world as an individual (a “dating entrepreneur”) and putting the power back in your hands so that you can innovate in your dating life and create the love you truly desire.


[More from Jasbina] —> [VIDEO] Intersections Match by Jasbina – From The Founder

—> [VIDEO] Are Some Women Really Just Unlucky In Love & Relationships?


Jasbina Ahluwalia

(00:51):  Hello everyone and welcome to Intersections Match’s Talk Radio, a monthly holistic lifestyle show focused on the continual evolution into the best versions of our authentic selves. This is Jasbina, your host. I’m the Founder of Intersections Match, the only elite national personalized matchmaking company focused on singles of South Asian descent nationwide in the country.

As a professional dating coach and matchmaker, I’m always interested in fresh perspectives from fellow relationship experts to help me provide the best possible service to our clients. I’m very excited to welcome author and fellow dating coach, Neely Steinberg, to our show today. Neely has authored Skin in the Game: Unleashing Your Inner Entrepreneur to Find Love, which we’ll be discussing today. Welcome to the show, Neely.


Neely Steinberg

(1:39): Hi, Jasbina. Thank you so much for having me.


Jasbina Ahluwalia

Dating Guide for Women – Writing One

(1:43): It’s a pleasure to have you. I think your book will empower many daters out there and I’m excited to share it with our listeners. To begin with, tell me what led you to write your book.


Neely Steinberg

(1:55): Having been single myself for pretty much all of my twenties and early thirties with a few relationships sprinkled in between that time span, I had purchased a million dating books. You should see my bookshelves. They’re full of them. I’m married now.

When I became a dating coach, I felt that women out there needed and wanted a practical framework that was less about rules and tactics to hook a man and more about being guided to come to decisions in their dating lives that felt right to them.

It’s about guiding women to come to their own answers, answers that work for them in their own life.

Elaborating on Dating Guide for Women – Writing One.



Jasbina Ahluwalia

Entrepreneurial Venture Into Dating

(6:51): Your book mentions three qualities as being critical to starting that entrepreneurial venture to find love. You mention desire, a problem-solving mindset and vision. Will you explain to our listeners the importance of these three qualities in their love life?


Neely Steinberg

(7:21): Yes, absolutely. The good thing about entrepreneurship is that it’s a life skill. You don’t need to have a certain personality type or have millions of dollars. A lot of people think of entrepreneurs being aggressive and self-starters. The good news is that entrepreneurship is really about a way of thinking and acting in your life. You can apply that to your dating and love life. As you are starting this dating and love venture, there are a few things that you need.

3 Qualities for Entrepreneurial Love Venture are:

  1. Desire
  2. Problem-Solving Mindset
  3. Vision

Elaborating further on the points above: Entrepreneurial Venture into Dating.


[More from Jasbina] —> [INTERVIEW] Jan Yager Interview – 125 Ways To Meet The Love Of Your Life



Jasbina Ahluwalia

Limiting Beliefs: 5 Steps to Overcoming

(9:45): Speaking of getting in your own way, you discuss a model for overcoming limiting beliefs, which hold people back in their dating and relationships. Can you share that model with our listeners? You can use the example of any limiting belief. Unfortunately, there are a lot out there that we succumb to sometimes. What is that model for overcoming the limiting beliefs holding you back?


Neely Steinberg

(10:21): There is a model.

  1. First:  identify those beliefs.
  2. Second: bring the beliefs to a conscious place.
  3. Third: accept responsibility.
  4. Fourth: replace all of this old crap that keeps you back and holds you down.
  5. Fifth: go out there and act.

Elaborating further on the model above: Limiting Beliefs: 5 Steps to Overcoming.



Jasbina Ahluwalia

Dating Board of Advisors: Who Do You Need?

(13:31): That’s very powerful. In terms of acting on your new, empowered beliefs, that is what gives you the evidence of your new, empowering beliefs. That becomes self-perpetuating in a positive way. That’s very helpful.

Your book recommends that daters assemble a board of advisors. Tell us about that. Our listeners would love to hear what you mean by that.


Neely Steinberg

(14:01): As an entrepreneur yourself, Jasbina, you probably have people mentoring you, coaching you, supporting you and advising you. The same thing is true for your dating and love venture.

A lot of people think, “I need to go it alone. It’s showing weakness if I have to rely on other people, work with other people or ask other people for help and support.” That’s a really ridiculous notion.

We ask for help in every other area of our lives. Yet, somehow, when it comes to one of the most important aspects of our lives, we say, “No, I don’t need anyone. I don’t need help.” I recommend assembling your board of advisors. This means assembling a group of people, enrolling them into this entrepreneurial journey of yours and asking for other people’s support, advice and mentoring.

Elaborating further on Dating Board of Advisors: Who Do You Need?


[More from Jasbina] —> [BLOG] Easily Make Friends But Not A Relationship – What Do I Do?

—> [VIDEO] Help! I’m Almost 40 And Still Single!

—> [INTERVIEW] Diana Kirschner Interview: Online Dating Strategies

—> [BLOG] Don’t See Romantic Potential…Is It OK to Continue?



Jasbina Ahluwalia

Entrepreneurial Dating: Date, Learn, Repeat

(16:32): That is a whole chapter that goes into a great amount of detail. Thank you for going over the broad strokes of this.

There is a concept throughout your book about thinking like an entrepreneur. This is a concept that I have a feeling is going to be new for a lot of people. It’s acting your way into thinking. Will you explain that concept to our listeners? It’s an integral and fundamental one. Tell us about that.


Neely Steinberg

(17:04) I think, in most aspects of our life, that we create our life through a lot of trial and error.

Dating is about trial and error, just as entrepreneurship is about trial and error.

You’ve created your business through taking action, seeing what worked and what didn’t and then going in certain directions based on your results. The same is true for dating.

What I talk about in the book is my “date, learn, repeat” model of entrepreneurial dating.

Elaborating further on Entrepreneurial Dating: Date, Learn, Repeat.



Jasbina Ahluwalia

Ideal Partner Qualities: Top 3

(19:02): They are simple. You internalize them as you go about things. In your book, you mention what you call an affinity list. I know this list comes up for a lot of people. Interestingly, you detail three non-negotiable qualities, which you site as fundamentally important in a partner for long-term love. This is something that belongs on every woman’s affinity list. Tell us about that.


Neely Steinberg

(19:33) Top 3 Ideal Partner Qualities:

  1. Kindness
  2. Trustworthiness
  3. Dependability

Elaborating further on Ideal Partner Qualities: Top 3.



Jasbina Ahluwalia

Ideal Partner: 2 Mistakes Describing Them

(21:15): I hear you on that. You mention two pitfalls in creating an affinity list. On one hand, they may be too specific, and alternatively, they may err towards being too vague. I agree with this.

Can you share with our listeners what you mean by that in terms of too specific or too vague?


Neely Steinberg

(21:39) Sometimes when I work with women and we start creating this list, they will get micro-specific.

They might say, “I want a man who makes over $100,000.” They list very specific things. I think that limits them a lot.

They are going to pass over men who might make really good matches for them because they’re so focused on these very specific qualities.

I encourage them not to get so specific that they’re missing out on great matches.

On the flip side, I encourage them not to be so vague. For instance, women will say, “I want a man who challenges me.” That’s so vague.

Elaborating further on Ideal Partner: 2 Mistakes Describing Them.



Jasbina Ahluwalia

Dating Reasonably: 3 Questions to Ask

(22:58): Let’s step forward to a first date situation. You recommend that a woman ask herself what you call the “three reasonablys” after every first date. What are those three? How do they help avoid becoming unconstructively extreme while dating?


Neely Steinberg

(23:26) Three Reasonably Questions To Ask Yourself:

  1. Did I have a reasonably good time?
  2. Was I reasonably attracted to him?
  3. Did we have a reasonable amount of common interests?

Elaborating further on Dating Reasonably: 3 Questions to Ask.



Jasbina Ahluwalia

Reflect After the Third Date

(25:57): Those are three really helpful questions. I completely agree with that. We went on the first date. We got through that. We get to the second date. Now we get to the third date.

After a third date, a lot of people are thinking, “Is there real potential here?” After getting past the third date, you suggest that daters reflect on four different questions. This is to assess whether the relationship has the potential to move forward. Let’s break these questions down for our listeners. The first one is, “Do I feel good about myself when I’m around him?” Tell us about that.


Neely Steinberg

(26:48): After the third date and future dates, I think it’s important for women and men to start asking themselves some questions.

  1. Do I feel good about myself when I’m around him
  2. Do I feel good about the bond and connection we’re forming
  3. Do we value similar things in life
  4. How is our relationship growing

Elaborating further on Reflect After The Third Date.



Jasbina Ahluwalia

Dating: How To Improve Yourself

(31:31): It’s all interrelated. The character traits that you mentioned before, such as appearance and a crash-and-burn situation, that’s something that if things organically unfold, there is time and interaction which reveals it. There is internal consistency there, which is really helpful.

You had mentioned “date, learn, repeat” in terms of the framework of your book. Let’s go with the “repeat” part of that.

In your book, you distinguish between iterative dating and incremental dating. It’s very interesting to see these parallels between the application of entrepreneur to business and love life.

Tell us about iterative and incremental and how they can both work together to be well-serving approaches.


Neely Steinberg

(32:31): As you know, entrepreneurs iterate in their ventures. They iterate in their businesses. They take certain actions. They make certain choices and decisions. They go in certain directions.

Some things work and some things don’t. Then they go in certain directions based on the actions that they take.

These are called iterations. You iterate your business as you go.

Bringing that back to the dating world, I talk about iterative dating. This is really about learning as you go.

It’s about taking action in the dating world. That means going on more dates, increasing interactions with men, getting out there and then learning from all of these actions that you’re taking.

Then you act again in smarter, more empowered ways. You can consider these types of things iterations of your dating and love venture. You’re iterating on the process of how you date. Did you want me to talk about incremental dating?


Jasbina Ahluwalia

(33:40): Sure. I think these are both important in terms of having your own compass and navigating.


Neely Steinberg

(33:52): Iterative dating will be different for everyone. We’re all unique. We all have different experiences and backgrounds. We have different experiences in the dating world.

How one woman iterates and the process of how she dates is going to look different from another woman and how she iterates in her dating life.

I walk the reader through examples of iterative dating and action for a number of different women in the book. We don’t have time to go through that.

The other part of this is what I like to call incremental dating. Entrepreneurs iterate in the process of how they deliver their services or products. They also make incremental adjustments. They are incrementally improving their product or service.

Bringing that back to your dating and love life, while iterative dating is really about the process of how you date, incremental dating is about improving you, the product.

Elaborating further on Dating: How To Improve Yourself.



Jasbina Ahluwalia

Dating Failures: How to Conquer Them

(36:27): Like you said, you have a list of about 50. These are skills that are applicable with every area of life. It’s self-serving. It’s not limited in that sense to dating.

Will you share with our listeners the importance of embracing failure in their dating lives? Tell us about that.


Neely Steinberg

(36:57): As an entrepreneur, Jasbina, I’m sure you are well acquainted with failure. Obviously, your business is a success but, as you built that business, you most likely made missteps, wrong turns and had disappointments. You kept going because you learned from those disappointments, setbacks and missteps.

In the world of entrepreneurship, they have conferences devoted entirely to the failures that businesses make.

There is a conference called FailCon that they have every year. It’s all about failures that businesses make.

At the end of the day, your failures become your assets. That’s the title of chapter eight, Failure is Your Greatest Asset.

Elaborating further on Dating Failures: How to Conquer Them.



Jasbina Ahluwalia

(39:08): I appreciate you sharing your insights with us, Neely. They’ve been very interesting. Do you have any last thoughts or a take-home message that you’d like to leave our listeners with?


Neely Steinberg

(39:20): We didn’t get to the rest of the chapters. One is about tapping into the power of your network. You know a lot more people than you think you do that can help you out in your love life and introduce you to people. Take advantage of your networks. There is a chapter about creating your own opportunities. There are one million opportunities that you could seize in your love life. I walk you through how to create your own opportunities.

The final message that I want to leave people with is that half the battle in this dating game is staying positive. It’s keeping a positive attitude, remaining hopeful and just being positive. That’s it. That’s half the battle. If you can do that, you’re halfway there. I would be honored for people to check out the book and let me know what they think.


Jasbina Ahluwalia

(40:24): Neely, how can our listeners get a copy of your book? The book is entitled Skin in the Game: Unleashing Your Inner Entrepreneur to Find Love. What’s the best way for the listeners to become readers of this book?


Neely Steinberg

(40:41): They can go to my website and go to the store section of the website. There is a link to the Amazon page. My website is “Trep” is common shorthand for the word “entrepreneur.” You can go to Amazon and type in the search bar, “Neely Steinberg Skin in the Game” and it will pop right up.


Jasbina Ahluwalia

(41:11): Thank you so much, Neely. It’s been a pleasure.


Neely Steinberg

(41:16): Yes, thank you so much.


Jasbina Ahluwalia

(41:19): In case you joined us late or would like to share this show with people in your life, I’d like to remind you that today’s radio show will be archived and available as a podcast on Intersections Match’s website, which is

I appreciate you hanging out with us. Make sure to join us for next month’s show. Take care, everyone.


What do you think?

What are some of the ways that women can empower themselves with to find the love they desier? Share your thoughts in the comments below.