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Ways to Succeed in the Male Kingdom Courtesy of the Princess of Darkness

"I have my male co-founder reach out to retail buyers because he's more likely to get a response."


"A potential investor asked me how I would run my business with a newborn while I was seven months pregnant with my first child."


These are a couple anecdotes our entrepreneurs have shared with us. 


We know women founders are treated differently than their male counterparts.


How can women succeed in traditionally male-dominated industries?  


For the answers, we went right to an expert, Amy Trask. Amy was the first woman CEO of a National Football League (NFL), a feat she accomplished in 1997, assuming the role for the then Oakland Raiders. She held that position for approximately 16 years and embraced the nickname "Princess of Darkness." 


Based on our conversation with Amy, here's the game plan for winning in a male-dominated space. However, remember that every team is different, and what works for one might not be the best strategy for another. 


Click here for the entire webinar moderated by Brigette Polmar of Brand Spoken. 


Don't Think About Your Gender: Looking around a room and seeing you are the only one with breasts can be intimidating. However, don't give the thought any energy. "I was the only woman in the room, quite often the only woman in many settings," Amy said. "I never gave it any thought at the time. If other people wanted to waste their time thinking that I was a woman in the room, well, then advantage me because they're wasting their time thinking about the fact that I'm a woman in the room. I'm not wasting my time."


"To Thine Own Self Be True:" Amy's mom's favorite quote became a mantra for her life. So my approach was, I don't care if you're bothered that I'm a woman; that's your issue. That's not my issue. People are tested all the time. They're tested because of their race, gender, ethnicity, age, educational background, etc. And it remains my view today - the best thing to do when you're tested is pass the damn test. So that's where I put my energy."


It's OK to Argue but Bring Data: Two weeks after being hired full-time at the Oakland Raiders, she realized that her boss Al Davis was incorrect about something.  


"'Excuse me, you're wrong,' I told Al. But, oh my gosh, I will never forget the look on his face when his head turned towards me. 'What did you say?' Al yelled. And I said, 'You're wrong.' 

She continued. "Well, Al yelled, and I yelled," she remembered. "After this went on for quite a while, he looked at me and said, 'All right, I got you.' If you want to disagree, go ahead, but come armed with data and information and make your argument. Don't just disagree to be disagreeable; have a reason for your disagreement and assert your reasons."


Have a Team, Not Just a Coach: Having more than one mentor and people to talk about your business is OK. "I believe strongly in the proposition that it takes a village," Amy said. "We can each help and learn from one another. I believe in learning and taking advice and input and suggestions and thoughts from everyone."


If the Goal of a Negotiation is to Make a Deal, Then Make the Deal: Amy mentioned that negotiations are typically done sitting across the table and talking. However, she approached them as an opportunity to collaborate. Amy would sit next to the other person and have a conversation. "A negotiation does not need to be a quid pro quo," she said. "It doesn't need to be a tit for tat. It can be a collaborative experience. If there are terms that are unimportant to me, I will start by saying to the party with whom I'm discussing this, if it doesn't matter to me, have it. If it doesn't matter to you, let me have it. And now, we're down to the few issues that matter to us both, and we can work to figure that out. Maybe we can make a deal, maybe we can't. But at least we're not wasting our time."


Get to Know People as…People: Men, women, non-binary - we all are citizens of the world. Asking about someone's weekend, family or life is a tool to build relationships. When you show that you care about your investors, customers, vendors, employees on a human level it makes doing business with them a whole lot easier. 


Want an Investment? Bring the Information: No matter an investor's gender identity, they care about the same things – can I get my money back? Can I trust this founder? Will this business be a success? Believe those answers are yes? Prove it. "Everybody I know who invests in businesses is looking for hard data and then a good feeling," Amy said. “So, I suggest providing all the complex data you can."


Take Accountability for Mistakes, and Others Will Follow: People make mistakes. However, the way you handle it defines you as a leader. Amy was open about her errors, hoping her staff would do the same. 


"I will tell you when I make a mistake because I need you to help me fix it," Amy said. "That encouraged my colleagues to tell me when they made a mistake so we could fix it together."


Vulnerability is a Skill: As mentioned earlier, investors need to feel a connection with a founder, to trust them. How can that relationship be established? By creating common ground. For example, you may have a learning disability that resonates with a customer or funder. By sharing your experience, you've built trust and differentiated yourself from others. 


Expose Yourself to Fears: After Amy left the Raiders in 2013, she became an on-air analyst for CBS Sports and CBS Sports Network despite being terrified to be on camera. "I worked for Al Davis for 30 years, and being on camera is the scariest thing I've ever done," Amy said. "Sometimes doing what scares the hell out of you can be a lot of fun."  


Defeat Gender Stereotypes: When someone makes a sexist remark, it can be jarring, and the immediate reaction is to get defensive. However, what if you approach the situation differently and lean into the comment. At the first NFL owners meeting Amy attended, an owner asked her to get him some coffee, assuming she worked there instead of being an invitee. 


"I said, 'sure, how do you take it?'" Amy remembered. "A few minutes later, the meeting starts, and the catering staff leaves. We all walk towards our seats, and the owner is across the aisle.


You could see the blood draining from his face. Well, I started laughing, and he started laughing. And from that moment on, he could not have offered me more fantastic support and encouragement throughout my career. I've been criticized quite a bit by women who thought I should have ripped into him. Well, you know what? To thine own self be true."


There is evidence that men and women can coexist and there are plenty of male investors that have backed women-owned ventures. The key is to keep playing the game and, as the Princess of Darkness says, "to thine own self be true." 

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