Ashlyn Gentry Yue of Attention Capital: “Create technology that makes it easier to find angels”

Create technology that makes it easier to find angels. In politics, EMILYs List (Early Money Is Like Yeast…it helps raise the dough) supports women candidates early in their campaigns. And the technology they use to find and connect with these women is stellar. We should invest in tech and online networking products that facilitate these […]

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Create technology that makes it easier to find angels. In politics, EMILYs List (Early Money Is Like Yeast…it helps raise the dough) supports women candidates early in their campaigns. And the technology they use to find and connect with these women is stellar. We should invest in tech and online networking products that facilitate these interactions. The more money we can give women at the start of their entrepreneurial journey, the more likely they’ll be able to stick it out and get other people on board.


As part of my series about “the five things we need to do to close the VC gender gap” I had the pleasure of interviewing Ashlyn Gentry, Head of Innovation at Edelman and Co-Founder and Managing Partner of Attention Capital, a media and technology holding company. Gentry is a renegade academic turned business strategist. She began her career in politics and academia, studying and working on political campaigns while earning her doctorate at the University of Texas at Austin. She most recently served as Senior Vice President at Palantir’s commercial headquarters in New York, where she led growth strategy teams for clients representing the world’s top media companies and brands. Previously, Ashlyn served as Vice President at Hill+Knowlton Strategies — WPP’s international public relations firm — advising the Global Chairman in operations and client affairs. Prior, she led programs at the Annette Strauss Institute for Civic Life in Texas. Ashlyn serves on the boards of The Pitch Academy and Sky’s The Limit and is an advisor to The 404.


Thank you so much for joining us Ashlyn! Can you tell us the “backstory” that brought you to this career path?

I studied and worked in politics for the early part of my career, and then shifted the skills I had learned as a political consultant into business consulting. From the vantage point of being a business consultant, there are so many common mistakes you see the most seasoned businesses making, and being an investor gives you the opportunity to help companies stop those common mistakes in their tracks and implement more innovative management approaches from the get go.

Can you share a story of your most successful Angel or VC investment? In your opinion, what was its main lesson?

We invested in an experiential media brand and when covid hit, they had to completely reimagine what it meant to engage audiences in meaningful experiences. The main lesson learned there was that if you have a strong level of trust with your consumers, they’re not going to abandon you when things get hard. They’re going to stand by your side and walk that journey with you. They’re going to try out whatever adjustments you have to make because they believe in what you do and what you stand for.

Can you share a story of an Angel or VC funding “failure” of yours? Is there a lesson or take away that you took out of that that our readers can learn from?

When you come across a company that you can’t stop thinking about, you have to stick it out until the end. If you have a good working relationship with the founder and business, and you agree on the main points of the transaction, don’t let the minutiae ruin it.

Was there a company that you turned down, but now regret? Can you share the story? What lesson did you learn from that?

I turned down an angel investment in a company that did outdoor picnics on the beach because I thought between the seagulls, the wind, and the colder temps, no one would choose that option over a romantic dinner in a nice restaurant. Covid turned that business into a goldmine. You have to keep your options open for completely new business models that are category creators. Those are the ones that will have the most upside. Take Airbnb or Uber for example. They took risks on business models no one had ever successfully tried before, and it paid off.

Ok let’s jump to the main focus of our interview. According to this article in Fortune, only 2.2% of VC dollars went to women in 2018. Can you share with our readers what your firm is doing to help close the VC gender gap?

There are now legal mandates requiring women on boards, and as a result, many investment firms have turned down offers because the startup didn’t meet that mandate. Picking a handful of rules, not guidelines, but rules that must meet your investment criteria for diversity is a critical step. If you don’t stand for something, you’ll fall for anything. As an investor, you have data and research and experience telling you that more diversity leads to better bottom lines. Ignoring it is to your peril.

Can you recommend 5 things that need to be done on a broader societal level to close the VC gender gap. Please share a story or example for each.

  1. More and easier access to mentoring for junior women. There are wonderful groups like Chief that offer mentoring for women who have climbed the ranks already. But there are grassroots issues that overtime compound and result in women being further behind than their men counterparts. We need to mentor women at the outset of their careers to help them when it’s most critical.
  2. More flexible networking opportunities. Many VCs hold networking opportunities that are after work at bars. Many working moms simply can’t make those. Hosting these types of events on the weekends ensure a higher likelihood that women will have some more flexibility in their schedules and can attend.
  3. Mastering interpersonal communication skills. Because investors have seen the same archetype of founder (white man) be successful in the past, there’s a bias towards that same type of archetype in the future. One thing that I’ve found breaks through that bias is killer pitch skills. Be memorable, get noticed, do something unique, craft a persona. Don’t let anyone forget they met you.
  4. Create technology that makes it easier to find angels. In politics, EMILYs List (Early Money Is Like Yeast…it helps raise the dough) supports women candidates early in their campaigns. And the technology they use to find and connect with these women is stellar. We should invest in tech and online networking products that facilitate these interactions. The more money we can give women at the start of their entrepreneurial journey, the more likely they’ll be able to stick it out and get other people on board.
  5. Support women-led VCs. Women raise other women up. The more we contribute to the success and notoriety of funds led by women, the more likely those dollars will trickle down to women founders.

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

There’s that old song…”anything you can do I can do better…” If we can create a movement where anything a man does, a woman could do equally, we’d be so much better off. Women simply don’t have equal access. Hell, there are still golf clubs in this country that don’t allow women members. We need to even every single playing field for all genders. Every double standard, every unfair expectation…gone.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

My life lesson quote is “treat everyone like you treat the janitor.” I’ve heard the quote “Treat the janitor like you’d treat the CEO.” But the problem there is it assumes that the CEO would otherwise garner more respect than the janitor. We need to flip that on its head. We need to treat leaders with a normal amount of respect, without believing that they deserve more of it than does anyone else. Leaders are human, they make mistakes, they sometimes have bad ideas, and the more we demystify leadership, the more accessible it seems to everyone, especially women and minorities.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this, especially if we tag them. 🙂

I’ve been reading a lot about Sallie Krawcheck and Ellevest lately. I’m a fan of simple products, simple revenue models, and simple values. I’ve been quite impressed with their success and reputation. Unfortunately I think many women don’t become financially literate until later in life, and easy-to-use tools and platforms like Ellevest help to combat and overcome that.

This was really meaningful! Thank you so much for your time.

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