Operating in traditionally exclusive industries and what you need to do to get what you want.

By Kendall Sherman

My last post garnered more attention than I ever could have imagined. I received hundreds of calls, emails, even hand-written letters from people from all over who expressed how much my experience and journey resonated with their own. I was humbled and at times brought to tears by the stories that I read. It also confirms what we all already knew- that there’s more work to do on the diversity and inclusion front, not only when it comes to entrepreneurship but also, and more importantly, in the VC industry.

What I didn’t know or perhaps expect was how hungry people were for more actionable advice. This was one of the main criticisms I received and after some thought, I realized that it’s rightfully so. It’s nice to read a success story but even nicer to know how to recreate it for yourself.

These are my humble tips on how to navigate and make an impact on really anything you want to do or be a part of, but specifically an industry that’s traditionally exclusive and homogenous in nature.

1. Don’t be afraid to be bold. This is a tough one and honestly, I struggle with this currently. It’s important, though, as it informs how you’ll interact with people. As POC/LGBTQ, and women, we’re often told, whether verbally or nonverbally, to shrink ourselves. Don’t be too aggressive; don’t be too loud; don’t be too…much. When you hear this over and over again, you’ll find yourself auto correcting before you’ve even spoken. Fight the urge to do this and recognize that your words are valid.
2. Don’t be afraid to speak up. A few years ago, I was in an interview for a role in recruiting. The interviewer looked at me and said “I want you to be a bitch — be as sassy as I know you can be.” Obviously this was an inappropriate thing to say and because I’m me, I told him as much. I didn’t get that job, which in hindsight was a blessing, but at the time I remember feeling very hopeless. I had very real bills and honestly didn’t have the luxury to pass on a job just because someone said something ignorant to me. I wallowed for 2 days then decided to keep pushing forward because no person, no job, no opportunity, is worth the dismantling of your self-esteem.
3. Do your very best, all the time.
4. Ask questions. I hate the idea of “asking the right questions.” This is just another way to silence someone, particularly people who might have not yet developed their confidence. No, you should ask any question that comes into your mind. I firmly believe there are no stupid questions and if someone makes you feel as though you are less valuable based off something you asked, then you are not in the right place and you should promptly move on. I practice this with our general partner Jeff Bussgang, who is an investor, operator, and educator. By asking me to send him 2–3 questions after every partner meeting, he created an open and safe environment for me to learn. Do I do it every time? No, unfortunately. But I know he’ll never be shocked to see an email in his inbox with the subject line “questions on questions on questions.”
5. Promote yourself with very little shame. Forget the humblebrag. As women and minorities, it’s common to have few advocates in your corner. This means you have to be your most devoted fan — we have to rely on ourselves to further our agenda more than anyone else. Have no shame, defend your ideas, and keep moving forward.
6. Focus on building authentic relationships with people. I’m not a fan of networking, so I opt for fostering real, organic connections with people who I am genuinely interested in learning from or more about. I try not to take or ask for blatantly opportunistic calls or meetings. People can see right through that and they don’t forget how fake it feels. Instead, I try to seek out people who are in positions I’d like to be in one day, or are thought leaders in a space that interests me. Of course you’ll both be aware of the potential synergies, but never start a conversation with that, no matter how tempting. Make the effort to get to know someone. Over time, you’ll build a working relationship and any opportunities that come from that will happen organically.
7. And finally, work hard. There’s a saying “work smart, not hard” that unfortunately doesn’t apply to everyone. You will have to do both, at the same time, everyday. To me, this is an ever-evolving thing, as where I am currently is never where I want to be in 2,4, or 6 years. I want to always be moving, learning, experiencing, or creating. You have to learn to listen to that inner voice that pushes you to finish a project at 1am AND that voice that tells you to step back and set it aside for the night. I’m still figuring this one out — any tips are welcome :)

Have an idea for a story or want to connect with me? Email me at ks@flybridge.com. Also, Flybridge is always on the hunt for entrepreneurs with industry disrupting ideas — shoot me an email with your info so we can connect!