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Female Founders: Dating Coach Damona Hoffman On The Five Things You Need To Thrive and Succeed as a Woman Founder

An Interview With Candice Georgiadis

Communication is king — I’ve had various staff members through the years, and each one communicates a little differently, but I’ve realized it’s important to clarify understanding when assigning work. Also, get your team on board with the overall goal and not just the specific task. They might have a better way of solving the problem that you wouldn’t reach if you were only thinking about delegating tasks.

As a part of our series about “Why We Need More Women Founders”, I had the pleasure of interviewing Damona Hoffman.

Celebrity Dating Coach Damona Hoffman has been coaching singles on how to find love online and offline for over 15 years. Her articles appear regularly in The LA Times and The Washington Post. Plus, she’s a regular on-air contributor to The Drew Barrymore Show, NPR, and NBC’s Access Daily.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I moved to Hollywood with a dream of working behind the scenes in entertainment as a casting director. I hit the ground running landing a job at CBS Television right out of college, and soon after saw a need to share what I knew with actors about personal branding and marketing. I taught classes on how to have the type of headshot that stood out from a crowd and how to ace an audition once you get in the room. Once I began online dating myself, I realized the similarity between a headshot and profile photo as well as a date and an audition. Once, I understood how the personal branding techniques I taught actors could apply to my own dating profile, I met the man who’s been my husband now for 15 years and realized I had the seed of a new business idea.

Can you share the most interesting story that happened to you since you began leading your company?

I believe that no experience is wasted. Even though I left my career as a TV executive to launch my dating coaching business, my path brought me back to TV in an unexpected way. After years of filming TV segments talking about dating, I was approached in 2015 to co-host a TV series. Since that time, I became the official love expert of The Drew Barrymore Show, I had a storyline on the Real Housewives of Beverly Hills, and I work regularly on Access (Hollywood) Daily. Now that I go on TV and advise people I used to watch about dating and relationships is pretty darned interesting and not something I ever would’ve imagined a decade ago.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I have plenty of stories of mistakes to share, but one of the funniest things I did that had an unexpected result was asking my cousin to come to my first matchmaking mixer because I didn’t have enough men signed up. I think he went just to support my burgeoning business, but he ended up getting more matches than anyone, and 5 or 6 women all felt they’d made a connection with him and wanted to date him. Good problem to have, I suppose, but then I had a lot of paying clients that I had to let down easy because he couldn’t date them all. I learned that you have to start somewhere. Since then, I try to better set expectations for clients.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My first business coach, Veronica Alweiss, had a major impact on my path. She was the one who got me to even admit that I wanted to leave my executive career behind to pursue this business. Beyond that, she was always very practical about the logistics of running a small business, and she helped me do financial projections for my business every year, which proved to be very valuable. Understanding how to set budget targets and track revenue month by month has been crucial to growing my business.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. According to this EY report, only about 20 percent of funded companies have women founders. This reflects great historical progress, but it also shows that more work still has to be done to empower women to create companies. In your opinion and experience what is currently holding back women from founding companies?

Starting your own company is a huge risk. If I didn’t have finances banked from years as a TV executive and a supportive husband, I don’t believe I would have felt confident enough to leap into entrepreneurship. As long as women are being paid lower rates than men and still overlooked for seed funding and loans, I believe that the risk of owning your own business will feel too great for many women to start businesses. When I was hosting the I Make a Living Podcast for FreshBooks, I heard stories from so many persistent and powerful women who often had to go to great lengths to get their businesses funded: some gave up ownership in their business to a man so they could get in the room at VCs, others had to answer personal questions like, “Do you plan to have kids anytime soon?” A VC would never ask a man that question in a pitch, and it’s completely irrelevant to understanding how she would run her business.

Also, mentorship is so important for many founders to get off the ground, and most people choose to mentor someone significantly similar to themselves. There are so few women CEOs and Founders that other women are getting left out of being mentored and getting access to important decision-making rooms.

Can you help articulate a few things that can be done as individuals, as a society, or by the government, to help overcome those obstacles?

We are in a time of a major cultural shift so I believe that in time, these beliefs will change but it’s still going to take a while. I’m heartened by the 2018 legislation in my great state of California that requires at least one woman to be included on boards of any publicly-traded company headquartered in the state. I would love to see women put in leadership positions organically, but it’s clear that more encouragement is needed to move us towards equity. In the last three years since the law was passed, the share of seats held by women in California has climbed from 15.5% to 29% in just three years. Clearly, this kind of mandate gets people moving in the right direction and I believe that more states and companies should take decisive action to inspire equity in leadership and encourage mentorship. I’d also like to see more funds earmarked for female founders at VCs and financial institutions.

This might be intuitive to you as a woman founder but I think it will be helpful to spell this out. Can you share a few reasons why more women should become founders?

I love that I get to create my own adventure as a female founder. I’m so much happier than I was in my corporate role because I have so much autonomy. Yes, there’s a bigger risk, but I believe there’s also a bigger reward. I’m now making more than I was as a high-level programming executive. I’m making my own content, running my own schedule, and hiring my own team. And that feels great!

What are the “myths” that you would like to dispel about being a founder? Can you explain what you mean?

Many people go into entrepreneurship because they don’t like answering to “the man” and having a boss. Although you are your own boss in entrepreneurship, you are still accountable to your clients and your team. Even though there’s no one above me in my company, on any given day, I’m managing the expectations of 15–20 clients so, in a way, I’ve traded one boss for dozens of them.

Is everyone cut out to be a founder? In your opinion, which specific traits increase the likelihood that a person will be a successful founder and what type of person should perhaps seek a “regular job” as an employee? Can you explain what you mean?

When you’re a founder, you must have a high-risk tolerance (with a dash of delusion.) There are many highs and many lows. There is an epidemic of depression and suicide among entrepreneurs, and we don’t talk about that nearly enough. If you already struggle with anxiety and depression, entrepreneurship could create a mental health struggle for you.

As a founder, you have to be willing to embrace a bit of the unknown. Ideally, you are someone who thrives on variety and you are also self-motivated. A founder must have a vision and the drive to serve, create something or solve problems.

Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each.)

You don’t need to be an expert at finances to run a business. I never thought of myself as “good at math” (another misconception about women that was deeply seeded in American culture when I was a kid.) I’ve never been very organized, and I don’t love spreadsheets. However, I’ve discovered that with tools like FreshBooks, I don’t need to be an expert in math or a spreadsheet whiz. I can easily be prepared for tax season because FreshBooks allows me to automatically generate reports, share transactions with my accountant, create invoices, and collaborate with my team in a format that makes sense for my creative brain. Their program really is built for owners like me who would rather put their focus on running the business.

Don’t try to do it all yourself — outsourcing the work that takes you a lot of time or prevents you from focusing on your core responsibilities will help your business grow. I used to edit all my content myself, but I’m a slow editor, and if I’m being honest, not that good at it. I found a freelance editor who could do better work in a fraction of the time it took me, and then I could free up my time to focus on the things I’m best at: building relationships with new clients and developing content. I also always struggled with balancing my books (and OMG I hated tax season) but since bringing on an accountant and using FreshBooks, I don’t have to waste mental energy on managing my accounts day-to-day and when so much is automated and can be prepared quickly and easily, tax season doesn’t stress me like it used to.

Communication is king — I’ve had various staff members through the years, and each one communicates a little differently, but I’ve realized it’s important to clarify understanding when assigning work. Also, get your team on board with the overall goal and not just the specific task. They might have a better way of solving the problem that you wouldn’t reach if you were only thinking about delegating tasks.

Do a little every day — I used to procrastinate on the things that I hated doing. I sometimes would have clients following up with me to get an invoice months later and even would realize I forgot to bill things entirely because I dreaded the invoice process before I had FreshBooks. Now it takes me literally 90 seconds or less to make an invoice which means I get paid faster.

Don’t be afraid to make a change — I’ve found myself stuck before with the wrong software, the wrong team, the wrong process simply because I thought it was easier to stay the course than make a shift. Having now been through four rebrands on my podcast, multiple marketing consultants, and more software than you can count, I can confidently say that if you feel inspired to make a change it’s usually the right call instead of trying to make something fit that isn’t the right thing for you.

How have you used your success to make the world a better place?

In Judaism (my religious upbringing), it’s a mitzvah to help someone find love. Every day, I get to do a job that brings people joy and sets them up for the most important decision they’ll ever make — choosing the person you’re going to share your life with. That decision impacts everything: your family, your mental health, and your finances.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

As a content creator and dating coach, I often speak about the power of our stories. I encourage folks to take note of the stories they tell themselves because sometimes the things we believe to be true about who we are and what we are capable of are designed to keep us safe but keep us from reaching our true potential or stepping outside of our comfort zone. I believe that the magic in our lives happens in that space of possibility when you can step back and say, what if that story is not true? And if that is not true, what if another reality is possible for me?

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Brene Brown! I have learned so much about human behavior from reading her books. Though I’m not a researcher, I see the value in looking at the patterns and emotions she studies. I believe that it has the power to impact how we show up in business and how we communicate with those we care about — the two things that matter most in my life right now.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.



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