5 Things to Succeed and Thrive as a Female Founder

Vanessa Ogle gives 5 tips for how to Succeed and Thrive as a Female Founder.

Interviewed by Candice Georgiadis

“Higher Hill Studios is an incubator to enable women and non-binary artists, songwriters, producers, mix and mastering engineers to have their voices and their work heard.”

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 wake up in the morning each day with my mind buzzing. In my first company, Enseo, I was thinking how to fix the technology gaps between home and where we spend our time during the day. The WiFi didn’t work at the coffee shop, the television at the hotel didn’t have a program guide to choose a channel. I couldn’t use my own music and Bluetooth to those great big speakers on the TV… why not? Because nobody had taken the time to invent the “glue” pieces of technology that made these people places work like home. The market was too small for big technology companies to bother with and too big for a single developer. That makes it the Goldilocks-sized market… perfect for a female founder with curly hair! I thought up technology solutions for how to bring first run Hollywood movies to our Armed Forces, how to bring Bluetooth music and Netflix to travelers in hotels, how to help protect students and teachers in their classrooms. These early morning brain children turned into inventions that earned me 70 (or so) US Patents.

I spent decades to refine a dream team of innovators who could bring my crazy ideas into a reality that became products that serve more than 90 million people each year. Now that my first company sold to private equity, I am indulging myself and my lifelong love of music.

My husband and I have been musicians our whole lives, and during COVID our hearts hurt to see our fellow musicians (who did not have day jobs in the C-Suite) struggling to make ends meet. We decided to take the opportunity to hire some amazing musicians to help us make our record.

I learned that making a record is almost exactly like making a technology product. You need a great idea, and an entire team of talent to bring that idea into reality. The people we met along the way were incredible musicians, engineers, and producers. They turned out to be almost all guys. I have a particular song on the album that is a girl power song, and I was disappointed when I was unable to use all women that one song as I had intended. I discovered that the music industry may be even more male-oriented than the technology industry. I know the talent is out there and this seems like a challenge that I am built to help provide answers for. I founded Higher Hill Studios initially for our own projects but soon it has taken on momentum of its own. I asked around and several major brands were also struggling to find diversity in their artist base. Higher Hill Studios will be teaming with some of the industry’s best-known producers and writers, sponsored by amazing brands (content providers as well as instrument brands) to incubate and launch female, non-binary, and disadvantaged minority musicians that otherwise might not have had a break. Everyone deserves a break!

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

When I was running Enseo, one of the leading hotel companies, who was a customer of ours, had an executive that told me to my face they were going to steal our intellectual property. I thought he was joking. He said it like a joke.. “Now that we have your recipe, Vanessa, we’ll see if their cooking (my competitors) tastes as good as yours does.” And…. he did. And ……I let him, because I was a Latina CEO who bootstrapped her small business, and the reputational hit to challenge the industry giant would have been impossible to survive, not to mention I didn’t have a spare 5-10 million dollars required to protect IP through the legal system. That is why one of the goals behind Higher Hill Studios is to not only incubate new artists and help produce great new music, but also to educate young artists on how to protect and maintain ownership of their content and catalogue.

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 remember my first trade show as a shiny new CEO with her newly birthed company. I was a skinny, young, Latina (still in my 20’s). I was so eager to meet my customers and represent my new company that I stood right in front of our trade show booth, proud and eager to engage. Over and over again people refused to speak to me because they wanted to speak to someone “important” or “someone who could make a decision”. They did not want to talk to the coffee girl, or the booth “fluff” at the reception counter. I was equal parts amused to be able to take people by surprise, as well as indignant at the blatant sexism that they didn’t expect the young woman to be the boss/owner/CEO/founder. That taught me one of the most important lessons of my career which is what I call Gender Judo. Any time someone attempts to gaslight or treats you as unimportant, let them do it, then do your job, and as they are off balance and surprised at their mistake… you have MUCH more leverage not only for that conversation, but for the foundation of your relationship as you choose to move forward. I can’t tell you how many times my team and I got a chuckle watching a room full of executives waiting to start the meeting because I had offered refreshments and then sat at the table after I handed out their coffee. They were still waiting for the CEO to show up.

None of us can 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?

I stand here alive and founding new companies because of my tribe. I am forever grateful to my friends and executives who have stood beside me and helped carry the load when my burden of being a founder and a single mother, was too much to carry alone. The men and women who surrounded me with love, support, and wisdom became my tribe. So while there is no one person, I do have an award-acceptance-list of people to thank and be grateful for. The insights of the women and men of my YPO small group (Young Presidents Organization) were the keys to overcoming imposters syndrome and instrumental to my success as they took time from their own businesses to challenge me to provide facts to back up my entrepreneurial instincts, and to encourage me to always doublecheck (but not second guess) my calculated risks to make big decisions. They also helped me carry the load on heavy emotional burdens that I was under to run not only my business but my family as well. My dear friends Stuart and MarrGwen whisked me away from reality to give me adventures where I received instead of being in charge of making all the decisions. My team at Enseo who followed me through the dark challenges of 911, the great recession of 2008 and then 2020. Today in our new adventure together, I couldn’t do this without my husband Paul Bullock who made me my first electric guitar and taught me that I didn’t have to spin all the plates by myself.

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?

I see three things that are holding women back from founding companies. Access to Capital, Council, and Confidence.

Women face a pervasive problem of discounted perception in their expertise. The gaslighting that so often happens by society, family, and even domestic partners kills whatever confidence a female founder manages to drum up. That means women must learn to find confidence in themselves.

If women can find a way to overcome family expectations and responsibilities, such as caring for their parents, spouse, children, the sad reality is that women have a harder time getting funding for their business than their male counterparts. Even if you look at the EY report above, the 20% is about funded companies. According to Crunchbase, only 2.3% of Venture Capital funding in 2020 went to woman-led startups, sadly down from the previous year. I attempted to get funding for my first company on several different occasions and it took 21 years to find the right capital partner.

Women also need great Council. Given the boy’s club at the top of most power pyramids, many of the leading advisors are not women (yet). Women founders need to find a way to break into the club to get access to great Council. This can be advisors such as attorneys and accountants but also a peer group or mentors to provide wisdom along the way. I found YPO (Young Presidents Organization) particularly helpful to me in my journey. I got to rub shoulders with some of the greatest business leaders in the world and as an insider, I learned so much that helped me in my journey. I can’t tell you how many times I have picked up the phone and called another CEO in this group to ask his or her opinion or expertise. I have also now received my fair share of inbound calls asking for my expertise.

Higher Hill Studios started out on the right path by finding and getting on retainer an iconic entertainment attorney to draft all our contracts related to the producers and musicians for our projects. Those clearly worded agreements, crafted with industry expertise have already made all the difference.

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? This is a game of numbers. We need more women founders, more investors who see the value in women leaders, and more women in the ranks to be trained up to become founders. We need more girls being encouraged that they too can become founders. Kay Koplovitz, author of Bold Women, Big Ideas is the Chairman and Co-Founder of Springboard Enterprises. Springboard Enterprises is a great example of exactly what is needed to encourage more women founders. Since they started in 2000, they have built a network of influencers, investors, and innovators who are dedicated to woman founders. Springboard not only encourages woman founders, but they also provide critical training and mentorship for women in their journey to raise necessary capital to grow their business. They have created more than 35 billion dollars in value in women led companies. Springboard was critical to me early in my journey. Kay is a valuable mentor, and I am convinced I wouldn’t have had the successful exit I did without her guidance and encouragement through the years.

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?

Women founders are good business. Woman founded business outperform their male founded counterparts. There are several studies including Boston Consulting Group and First Round Capital, the Kauffman Foundation, that show that woman founded businesses receive less funding, yet offer significantly more returns (one study says 35% higher return) than all-male teams. Women also have a history of being more intrinsically led (instead of financially led) when they start their entrepreneurial endeavor which means they are more likely to make the sacrifices necessary to be successful against the odds of any founder’s journey. Results, as well as female founders leading with compassion and empathy, bring products to the market that serve the capital markets as well as society.

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

Myth one: There can be work life balance as a founder. As a founder there is no work-life balance. You must live, eat, and breathe your new company. While you may be superwoman, nobody can be all the things, to all the people, all of the time. If you have a family, they MUST be onboard for you to be a successful founder, and conversely your team must be in support of your family responsibilities. It took me almost twenty years to find a life partner who was supportive of me being a founder and all that entailed. My life as a founder became doubly more fulfilling but exponentially more complicated when I added children. My children are a part of my team, and they went along with me on business trips until they started school. My youngest child at one point asked for her own business cards because they heard me say “I couldn’t do this without you” so often. She was convinced they deserved the same CEO card that I had, which they got, but their title CEO, was for Chief Executive Offspring. I was not leaving them when I went on a business trip, I was doing my job, just as they were doing their jobs by going to school. Now, several times a year we sit down with the school and extracurricular calendars, and we prioritize as a family. The kids choose the most important activity for me to be at each month. I never missed that priority event, but when I do travel, they feel included and part of the decision process.

Myth two: Women are too emotional to make a good founders or leaders. This is a particularly toxic myth. Having and showing feelings is not weakness. Empathy and respectful authenticity are critical to attracting talent, growing a great corporate culture and feeding a healthy business. Women’s many roles as daughters, mothers, and wives, is what gives them richness and strength as a leader. It takes courage to feel, courage to cry. There is nothing more powerful than a woman who is willing to feel and who listens with empathy to her customers and team. That combination of listening and empathy breeds amazing products and a loyalty of team who will move mountains to make miracles happen.

Myth three: Female founders should only seek out support and encouragement from other successful females. This is not only a myth, but impractical. I do have some amazing women in my support system, but my network and support would be weak by comparison if I exclude all the incredible men (mostly white men) who have lent me their wisdom, support, and encouragement. Find the smartest and best people to be your support system and on your team. You are the female founder, surround yourself with a diverse group. At Higher Hill Studios we will be focused on incubating/launching new artists who are women/non-binary/diverse but we will not exclude producers, engineers, musicians who are men… we are grateful for the people who are willing to commit their time and talent to help these underrepresented new artists enter the market.

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?

If you want everyone to like you, if you want precise repeatability in your schedule each day, if you want someone to constantly tell you when you do a good job, if you want nice long relaxing vacations… these are not things that happen when you are a founder. If these things are important to you then find a great job at a great company (maybe even supporting a great woman founder or executive) and make a difference that way. I certainly wouldn’t be successful if I didn’t have my team to support me.

Being a founder requires tireless dedication and singlemindedness. Everyone will tell you how and why your business will fail, you have to believe your business will succeed no matter what noise the naysayers make. There is a level of calculated risk taking that is mandatory for being a founder. There is a singlemindedness required to be able to see future success by taking risks that other people think are… well….crazy. (Like putting a second mortgage on your house to pay payroll or buy back debt from a bankruptcy court). The challenge is to balance this singlemindedness with a willingness to listen to the wisdom of your tribe and hear when you need to pivot or to adjust strategy or approach to be more successful.

Ok super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Woman Founder?” (Please share a story or example for each.)

1. Ovaries of Steel (Tenacity) Being a founder is a difficult and lonely job. It means making all the hard decisions and not taking all the credit when a win comes your way, but by contrast any mistake of your team is yours to shoulder. If you are a woman founder you can expect the word Bitch to be on your guy competitors’ lips and even some of the small-minded people in the middle of big business. Many men do not like being told no by a woman. It is just a fact. It takes enormous ovaries of steel (these can be metaphorical, and you don’t have to be born with them or even still have them). I can tell you it took grit and tenacity it took for me to lead businesses I founded through the crisis of two decades, including 911, the recession of 2008, and again the covid crisis of 2020… but it all paid off in the end. I sold my first founded business to PE and now am happily working on Higher Hill Studios.

2. Gold medal in Gymnastics (Talent)

There is a lot in common with being a woman founder and a gold medal gymnast. You need unlimited amounts of strength, flexibility, grace and great timing. You have to take time to build your talent. That is never easy. It takes endless days of training and hard work and a pile of breaks and bruises. But no matter how black and blue you feel, when it is your turn, you must look around with confidence. You also need great coaches and trainers to be at your best. You are part of a team and the team you build around you makes the difference in the toughest business competitions.

3. Black Belt in Gender Judo (Tolerance) This means you move out of the way of sexism and let people make their own mistakes. As you are unwittingly undercover as a CEO, when people presume you are the admin, the coffee girl, the nanny to the CEO or any other position, just have a sense of humor, move out of the way gracefully and then offer a hand down to help that person regain their balance when they realize their mistake. They will remember that moment and you will have won the round. It is also critical to understand that Gender Judo is a team sport. My team has been told things like “can’t you keep your Bitch on a leash?!” (and worse things) by the small-minded who don’t want things shaken up by a woman. I know my team would rather have punched the jerk, but they didn’t. They dug down, found their balance and Gender Judo’d their way to win the business despite the bias. There were also times we chose to walk away because it wasn’t worth it. Remember your team is working harder and smarter to work for you than they would if they had a male founder. Respect and appreciate their effort.

4. Rockstar Entourage (Tribe) To survive and thrive as a woman founder you must seek out and curate your own TRIBE of women and men (and all under the rainbow) to believe in you. This tribe will be experts for support in your business such as the best attorneys and accountants that you can find… because being a founder means reading someone else’s music, and also writing your own and you need a GREAT attorney and accountant to make that happen. You also need family, or family of your heart to support you through the highs and lows of being a founder. There will be difficult times when you have to make decisions to keep people in your life as your tribe or to expel them from the island because they do not support you.

12 Years ago, I was a single mom of a 2-year-old and a 6-week-old infant and up for E&Y’s Entrepreneur of the Year award. I was still nursing, and the team at E&Y worked miracles convincing me to stay until the end of the award show. I didn’t realize then that EOY is the Grammy’s of the business world. When the spotlight turned my way and my image was huge on the wall and I won the award, I was blinking in confusion and concern that my very sore boobs were leaking milk. (I’m pretty sure the other 10 CEOs in my category didn’t have to worry about that, did they!!). My date for the evening looked at me and said, “There is no way YOU won this award!!” Wrong answer sir. In sharp contrast my husband Paul was recently at another award ceremony where the other nominees had “Jesus tech” …they actually made blind people able to see… and my sweet sweet Paul leans over and says “Nobody deserves this award more than you do!” And when they called my name, he jumped up, pumped his fist and yelled YES!!! That is a rock-star entourage. He celebrates me being celebrated.

5. Magic Mirror (Truth) ”Mirror, mirror on the wall…” Every morning you need a magic mirror that shows the reflection of who you really are and who you are going to be. The magic mirror allows you to speak to the inner you with encouragement and compassion in the hardest of times. It also allows you to look at your 13-year-old self and show her what a badass you are now. I was the stick-skinny nerd who carried a briefcase in middle school and was constantly made fun of for fuzzy hair, weird clothes… and it goes without saying the briefcase. I look into the mirror at that 13-year-old Vanessa and show her how we invented products that help change the world, I show her our Rock Star husband and amazing children, I show her that being nerdy is cool and wins actual U.S. Patents. Now I get to show her the music that Higher Hill Studios is releasing that might change the life of young artists. She is much more impressed with me than I allow myself on any given day.

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

I have a passion for the voices of women and children to be heard. Men do a much better job of speaking and speaking loudly. In many cases men who abuse power also use their voices to speak over the wants and needs of women and children. In my first company, Enseo, we brought technology products to market allowed the voices and needs of teachers, students and even housekeepers at work to be heard if they were in danger and needed assistance. Now I am pivoting to the creative part of my journey to have the creative voice of women to be heard. I want to lift up women’s talent in a world of men. Women (of any age or gender) have something to say that is worth listening to. Higher Hill Studios is an incubator to enable women (and non-binary) artists, songwriters, producers, mix and mastering engineers to have their voices and their work heard. We are working with the world’s leading brands in music to help curate and bring to light some amazing talent.

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.

I would inspire a movement for educators and parents to focus on middle school children to lift up girls (and non-binary kids) to speak up and be heard. I see a shift happening in middle school where the boys overtake the girls in willingness to speak out and stand up with new ideas. In an elementary school classroom when you ask a question, all the hands go up. As soon as you hit middle school only the boys’ hands shoot up. We need all our children, not just our boy children, encouraged to speak out, to stand up for what they believe in… and to speak their truth. We will not have equal amounts of women founders until girls and boys can be taught that thought leadership and boldness is every bit a prized trait for girls and boys. Innovation is not “going with the flow” and many more women would be founders if they were called Bold instead of B**ch when they were not subservient and quiet to the men around them.

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.

I want to thank Gloria Steinem for her work on individual rights and equality. Higher Hill Studios is all about surviving through the difficult times in one’s life one step at a time to make it to the higher hill. Gloria has fought for people’s rights to reach their Higher Hill. I would value Gloria’s insight on how I might use my influence to support women and human rights as a successful founder.

I also want to give a special shout out to Chris F. Martin IV. Our recent conversations really led me to the path I am on today with Higher Hill Studios. Thank you for the conversations (not to mention I LOVE my new guitar from the custom shop). Rock ON!