“Five Things We Need to do to Close the VC Gender Gap,” with Angel Investor Kelly Keenan Trumpbour

Jason Malki
Jul 23, 2019 · 23 min read
Photos by Janel Conlan

Angel investing is a spend on power and influence.
One of the conditions I made for myself when I started was to only invest in companies I thought had a serious chance of returning a profit to me and the founders. I’d spent a lot of my career working with nonprofits and PAC’s, a donation-based system. I earned a salary, but the payoff for me and for any of the women we convinced to donate to our cause was that we were doing good in the world. I still strongly support the nonprofit model and the heavy lift it does in arenas like the arts, social justice and education. But women especially are a little too prone to accept “thank you” as payment. When I started See Jane Invest, I didn’t want to write off a bad investment as “doing good” in the world. I knew the chances were high that I would lose money. As a financially risk averse person, I felt sick at the thought of writing a check for $10,000, $25,000 or $50,000 with the understanding that it wouldn’t come back to me. I had to find a way to get comfortable with that extreme discomfort. I rationalized it by considering the social media influencers out there who were charging thousands of dollars to attend one of their conferences or join their mastermind group. Some of those groups are worth it, many are not. When I drop thousands of dollars into a start-up, I am doing grassroots level betting on myself and the founders. It’s an education. I could justify that it helps me dive deeper into my strengths and weaknesses in gauging business and talent. But if it turns out that I’m terrible at picking good start-ups, I know the money didn’t just burn up. My investment is also a spend on power and influence.
I back women exclusively. If all I accomplish is showing up as a woman investor who gets other women’s companies oxygen, I’ll proudly take that as a damn good lin- item spend on slingshots pointed at the glass ceiling. In my experience, the angel investing community, particularly the women in it, is great at sharing information. It has introduced me to financial experts and business mavericks I may never have met.


part of my series about “the five things we need to do to close the VC gender gap” I had the pleasure of interviewing Kelly Keenan Trumpbour. Kelly is an active angel investor, venture capitalist and producer based in Baltimore, Maryland, who funds women-led startups and films. She has served as a Founding Venture Partner at NextGen Ventures, a board member of the Baltimore Angels, and mentor to over 50 companies. A sought-after speaker and media commentator, Kelly has appeared frequently as a guest judge on CNBC’s Power Pitch; Fox Business’s Elevator Pitch; and addressed audiences at Harvard, Berkeley, The United Nations and many others around the globe. Kelly is currently working on her non-fiction book, Invitation to Risk. You can learn more about her work and listen to her podcast at See Jane Invest.


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

What brought me to investing was a desire to level up how I engaged with risk and to be present as a decision-maker in rooms where women were pitching ideas. Risk is surprisingly satisfying to me but taking female founders seriously is huge. After being a lobbyist on behalf of women and minority-owned businesses and helping to fund and train female political candidates, I know women face funding and power disparities. Right before I became an angel investor, I pitched an idea to someone who cared more about sleeping with me than taking my idea seriously, and I wanted to spare other women from that. I wanted to be the decision maker, distributing cash and making crucial connections with and for women.

This impetus started eight years ago, when a perfect storm was brewing in my life. For health reasons, I’d had to step away from my job helping young women run for political office. My husband and I were hoping to start a family, but in undergoing IVF, I’d had a debilitating reaction to one of the treatments. A few months later, I broke my arm. For over a year, I lost the use of my right hand. Though I was emotionally and physically at a low point, I’m a working breed. Forced to stay home too long, I start chewing furniture.

When the head of a local public radio station asked me to join the station’s community advisory board, I was thrilled. Before coming to Baltimore I’d lived in Detroit and worked in Mayor Dennis Archer’s Executive Office and on social entrepreneurship projects. I saw urban planners studying Baltimore’s Inner Harbor renaissance as a model for Detroit, but Baltimore was hard on itself, apologizing for having more problems and less offerings than D.C. or New York. At the first meeting, I asked why more programming didn’t exist that profiled what Baltimore had going for it.

The man who’d invited me to join the board told me he’d like to hear more about this idea. This turned into me pitching him a radio show I’d host and produce myself. At his suggestion, I put together some interviews with local thought leaders and social entrepreneurs. One of them was my friend Jess Gartner who was finishing her residence with Teach for America and just beginning work on her FinTech startup, Allovue.

My contact was always enthusiastic about the show’s concept, but not much seemed to be happening. He kept inviting me to talk about next steps over dinner. Amicable and professional, these dinners left me feeling optimistic.

But by the third dinner, it was harder to keep the focus on my radio show. He told me about a friend who had gone through a divorce and rented an apartment for a younger woman in the city. He asked me what I thought of this arrangement. Didn’t it seem more sensible than dating and marriage? Would I ever like something like that? This man was my father’s age.

Doubt flooded in. I asked him if I was naive to think the show had a shot. He said it did have potential. But he also asked why someone who looked like me wanted to work in radio because “you don’t have the face for it.” He said we could keep discussing things as long as my husband didn’t mind us being out together.

Him bringing up my husband enraged me. He’d met my husband and me at a station-sponsored speaker event about adoption, and I’d already told him the flexibility of producing a radio show would allow me to start a family in a way my work in Washington politics had not. I was frustrated and angry but hell bent on getting the show considered by the producers. I made the mistake of wanting to win the pissing contest and said yes to drinks at his nearby home, thinking I was holding my ground and proving unflappability. Instead, I was putting myself in a potentially dangerous situation. Less than an hour later, the night ended with me pushing him away as he leaned in to kiss me. I rushed out his front door and couldn’t get in my car fast enough.

The next day he emailed me asking if I would be willing to have a phone call with him. I had already told both my husband and my therapist about what had happened, and their support made me feel less shaky. I took the phone call and he apologized, claiming there were mixed signals. I asked him again if I was wasting my time pursuing the radio show. He swore I wasn’t and promised he would help connect me with the producers. I continued pitching, and nothing came of it. While I'm sure that had to do with my minimal training in radio journalism and my amateur demo tapes, even if I had all the talent in the world, it felt like my show never had a shot in hell. The senior producers were kind to me, but my meetings with them and the technicians were constantly rescheduled. Sometimes this was because more established shows needed them. On more than one occasion, it was because my name had never been entered into the calendar.

I continued to work on the Advisory Board because I cared about what the station represented. I didn’t want what happened to destabilize the station’s sometimes precarious future in Baltimore. When I saw the man who took me out to dinner, he often took me in from top to bottom, especially if I was wearing a dress or skirt, but he made no other advances. I felt stupid, overly ambitious, naive as hell. It didn’t help that when I told the story as a warning to another female colleague who was trying to get her boss a show on the station, her response was, “You really need to stop telling people that story, it sounds bad for you.”

One day I overheard the same man ask someone how he could join the Baltimore Angels, the largest angel investment group in Baltimore. By then my friend Jess Gartner, who I had interviewed for the demo tapes, had her own pitch deck ready, and I asked her if there was any way I could help. She asked me straight-up if I was an accredited investor and could participate with the Baltimore Angels. She was about to go in front of them. In every room she had pitched so far, the room had been full of men.

I didn’t completely understand what “accredited investor” meant. But I wanted to get into that room before the man who had taken me to dinner. Though I hadn’t needed a radio show for income, Jess was pitching a full business. She was putting everything into her start-up. If I had trusted someone who I looked to as a potential mentor to give my idea life, only to have him seemingly amuse himself at my expense, what would women like Jess be facing?

Becoming an angel investor wasn’t about me being nice or lending a hand. It certainly wasn’t about swooping in to save damsels in distress. If you have ever met a successful female founder, they can take care of themselves just fine. Getting into angel investing was saying to the founders, “You and I both deserve to profit — in this venture, sure — but in the world too. I promise to be the one person you don’t have to waste any brain cells wondering if I’m looking down your dress or grabbing your ass. I promise to listen, see you, and understand what it took for you to get into this room, whether or not we wind up working together. What I care about is whether or not you have a good plan and we can make an impact together.”

I became the second woman to join the Baltimore Angels. Later, I became the first woman to sit on their board. Jess’s company was my first investment. It was satisfying as hell to switch from being the person who hoped someone else would see my value and open doors for me, to becoming the person I expected would be my best source of power and influence. One of the best things I have ever done for myself, as much as for any founder, was to uphold the integrity I deserved, create the opportunity I craved, and set the terms I wanted.

Photos by Janel Conlan

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

I’m proud of all my companies, but the two founders that have continually wowed me are Jess Gartner of Allovue and Polly Rodriguez of Unbound. They are very different companies. Allovue is in the FinTech/EdTech space while Unbound is SexTech. Allovue was my first investment, and the company hasn’t just weathered major shifts in the market, they’ve adapted and grown their offerings out of Baltimore.

Unbound blows my mind. They are one of the only sex toy companies where women are designing and selling the products themselves. They even took on the New York MTA for rejecting their ads for sex toys when the MTA had allowed erectile dysfunction ads displayed.

What both companies have taught me is how crucial it is for founders to not just have stamina, but to know what to do with it. Most investors know that CEOs need to have the skills to survive market shifts and create ample runways in everything from funding their companies to creating leadership pipelines, but a subtler and ridiculously important trait is to know how to focus their stamina. Start-up culture is filled with people who can just go and go and go. Having energy for energy’s sake and the ability to dream up a constant supply of options doesn’t do any good unless there is clear purpose behind it.

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?

While I will always stand by what initially drew me to a company, from a business perspective, there have been companies I wanted to succeed, but I unfortunately got caught up in the meaning behind them and ignored huge red flags.

Amanda Steinberg at Daily Worth deserves so much credit for opening up the conversation around women and finance, but by the time I became an angel investor, Daily Worth was shifting. One of my friends at the Baltimore Angels had backed the company and when they raised another round, I was eager to believe there was more for Daily Worth to do. Interestingly, my friend declined to follow from his initial investment and didn’t push me to back the company. That was the first warning I ignored. In several conversations with Amanda, there was no doubt she had the grit and tenacity a founder needs. During my due diligence, she did her job by showing me why her vision could work, but I didn’t do enough of my job, spending more time with questions like, “What could go wrong here? What problems can’t be fixed by grit and tenacity?”

Two years later, Daily Worth was over. The lesson I took away was to double down my skepticism when there’s a start-up solving a problem I want to see resolved, and I find the founder extremely capable. Just because I believe in what they’re doing and the founder is driven and talented doesn’t mean anything will come of it, even if those kinds of companies are like catnip to me.

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

I talk to so many incredible female founders whose vision and creativity blow me away. It’s something I’m writing about quite a bit in my upcoming book, Invitation to Risk. I’ve basically just accepted FOMO comes with the territory. Often the regret isn’t about losing a windfall — very few companies that have approached me have been around long enough to realize massive wins — but the lost opportunity of being part of a company’s journey, especially when the company means something to me.

About a year ago, I passed on the chance to invest in Mr. & Mrs. Smith Hotels. I’ve been one of their customers and members for over three years, and I have always loved the experience. When they opened up an investing round, I seriously considered it and knew I would enjoy it. Ultimately, I passed because I wanted to focus on other companies in my portfolio, but I remain very curious about them.

I think it’s okay to feel a little burn of regret. If you don’t feel that in this business, you are probably overextending yourself and your resources.

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?

When I began angel investing, I decided to give my new focus a name. See Jane Invest summed up why I was shifting from being a conservative, risk-averse investor to someone who willingly writes checks to companies that have about a 90% chance of evaporating.

Before investing, I worked in politics, raising money for women candidate PACs and training college-aged women to run for office earlier in life. The biggest roadblock to this work was that women were rarely the ones writing the checks to fund political campaigns. Back in the early 2000s, they were rarely running for office. Women were not as active in funding female politicians or choosing to be one, and so there were few role models for other women to emulate. When my friend Jess Gartner created her start-up, Allovue, and explained that pitch after pitch, she was walking into rooms full of men, I recognized the exact same issue. Jess was in the minority of founders. Fewer women were creating start-ups.The critical financial backing opportunities were coming almost exclusively from men, and those opportunities were not getting extended to women founders at the same rate as their male counterparts.

I knew two things when I got started: First, I didn’t want to create a start-up. That left investing as the only way to help solve the gender gap. Second, when I invested, I was going to invest in companies that had a female founder.

I actually remember one of my first Baltimore Angel pitch meetings, when one of the other investors walked up to me during the cocktail hour and asked, “What’s your vertical?” I was so new to investing that I hadn’t even wrapped my brain around EdTech, MedTech, FinTech, and so on… so I just answered back, “Women.” That was my focal point. It actually helped me avoid overwhelm.

See Jane Invest was me, as a woman investor, publicly becoming a model for funding women-led companies. I am asking women to look at me, see what I’m doing, and ask how I’m doing it so it’s not a foreign concept.

Can you recommend 5 things that need to be done on a broader societal level to close the VC gender gap.

  1. “Accredited Investor” shouldn’t be a mystery term.
    I know “accredited investor” is a mystery term because when I was asked point blank if I was one, I didn’t completely understand what the term meant. I am a lawyer with an MBA. My day job used to be explaining how women could become more financially active in funding women’s political campaigns. I’m privileged enough to actually qualify as an accredited investor. And I still didn’t know what an accredited investor was and that I could become one. This alarmed me. If someone with my background, education and access to wealth doesn’t understand “accredited investor,” how many women like me, who might find this interesting, rewarding and challenging in the coolest ways aren’t in the game? It’s one of the reasons I am writing a book about this.
    The term is so much more pompous than it needs to be. When they hear the term, most people ask, “Is there a test involved?” As if you have to get certified for it, like a driver’s license. When you attach “investor,” it sounds like a math test. All it means is that you are rich enough to make the investment and, if you lose all your money, you won’t be asking the federal government to bail you out. Usually, the only person “certifying” that you meet the SEC (Security and Exchange Commission) definition of accredited investor is you. It’s a checkbox on the documents you sign before wiring money, affirming that you meet the requirements: having a net worth (excluding primary residence) of $1,000,000 or having an annual income for the last two years of $200,000 or more, if you are single, and if you are married $300,000 for the last two years.
  2. Risk aversion is the ultimate investor asset.
    Most people are surprised to learn that I am risk averse in my daily living, and especially in finances. I was taught not just to avoid debt, but to fear it. Credit cards could be as dangerous as drugs and alcohol. I was raised and mentored by people affected by the Great Depression, who instilled in me the craving for multiple financial back-up plans, and serious control over my money and independence. I don’t sleep well unless I know I have savings for the long term, the shorter long term, the short term, and the short-short term. I also stuff a twenty in my glove compartment in case I find myself without my wallet and out of gas. This borders on paranoia if not neuroticism, but it serves me really, really well.
    Angel investors and venture capitalists have an image of being players and high rollers. In a sense they are. Our investments are so high risk, they can feel close to gambling. But my risk aversion is my best friend in risk. I know deep down I can trust myself because of my conservative streak.
    Before I began investing, I sat down, appraised my own finances, and found my discomfort zones. I didn’t start with how much money I needed, I started with how much money I wanted, to feel comfy-safe. This tamed my scarcity triggers. I was looking after my own well-being as much as after someone I love. I don’t want someone I love to be operating on what they need to live. I want them to have a buffer to enjoy life.
    With that lens, I appreciated how fortunate I was. This mental freedom opened up the desire behind becoming an angel investor. Investing could round out my world in a satisfying way, and I wouldn’t wake up in a cold sweat, pacing my kitchen at 4:00 a.m., wondering if everything was okay. Enough in life triggers these feelings. How much I devote to my investments is something I can control. There’s no reason to enter a space of what the hell am I doing? So I set buffers. I paced investments, started slow and built over time. Risk aversion gives me carte blanche permission to say “no” more than I say “yes” to investments. When I want to invest, I know my desire has popped to the surface by making it through my risk aversion litmus tests.
  3. Angel groups should offer longer new member grace periods.
    Most angel groups allow prospective members to come to one or two meetings and see the pitches. There’s often an annual fee of around $1000+ dollars to officially join the group. That comes with the expectation of minimum annual investments ranging from $10,000 — $25,000 or higher. Being in a group setting is a great way to learn about investing. It was helpful to hear investors talk about what attracted them or turned them off in terms of company pitches. I’d love to see more angel groups offer longer look/see windows, maybe 3–6 months, and a junior dues option where you still have to be an accredited investor and all information remains confidential, but there is no annual investment requirement and the dues are only $100-$500 dollars. That may attract more revenue for caused- based angel groups and bring people who are on the bleachers into the game.
  4. Angel investing is a spend on power and influence.
    One of the conditions I made for myself when I started was to only invest in companies I thought had a serious chance of returning a profit to me and the founders. I’d spent a lot of my career working with nonprofits and PAC’s, a donation-based system. I earned a salary, but the payoff for me and for any of the women we convinced to donate to our cause was that we were doing good in the world. I still strongly support the nonprofit model and the heavy lift it does in arenas like the arts, social justice and education. But women especially are a little too prone to accept “thank you” as payment.
    When I started See Jane Invest, I didn’t want to write off a bad investment as “doing good” in the world. I knew the chances were high that I would lose money. As a financially risk averse person, I felt sick at the thought of writing a check for $10,000, $25,000 or $50,000 with the understanding that it wouldn’t come back to me. I had to find a way to get comfortable with that extreme discomfort. I rationalized it by considering the social media influencers out there who were charging thousands of dollars to attend one of their conferences or join their mastermind group. Some of those groups are worth it, many are not.
    When I drop thousands of dollars into a start-up, I am doing grassroots level betting on myself and the founders. It’s an education. I could justify that it helps me dive deeper into my strengths and weaknesses in gauging business and talent. But if it turns out that I’m terrible at picking good start-ups, I know the money didn’t just burn up. My investment is also a spend on power and influence.
    I back women exclusively. If all I accomplish is showing up as a woman investor who gets other women’s companies oxygen, I’ll proudly take that as a damn good lin- item spend on slingshots pointed at the glass ceiling. In my experience, the angel investing community, particularly the women in it, is great at sharing information. It has introduced me to financial experts and business mavericks I may never have met.
  5. Women should own the label “wealthy.”
    Just by checking off the box that says “I am an accredited investor,” you are publicly declaring your wealth. As a society, we have ways of expressing wealth that are more comfortable than others: designer clothing, expensive cars, luxury vacations, anything put on Instagram to make people from high school jealous. But status symbols are often mirages. You never know who is actually wealthy, who is talented at finding quality knockoffs, and who has mortgaged their life to keep up appearances.
    Unless you are a real risk junkie and feel like taunting the SEC and the stability of your star-ups’ future, by being an accredited investor, you actually affirm that you have money in the bank, lots of it. This is psychologically hard to do. It exposes you. There’s a reason why history is littered with aristocrats and royalty installing walls, moats, and pointy things around them so they could be admired for being rich and (theoretically) well-bred, while keeping the world outside their gates. But when you are an angel investor, especially in groups like the Baltimore Angels where they focus on supporting regional success, you come down from lofty living and put your skin in the game with the founders.
    Becoming an investor also might suggest you are a master of money or know how to always pick “winners.” This can trigger imposter syndrome. Anyone in the start-up world knows zero correlation exists between investors and financial certainty, it only looks that way from the outside. When I started investing, my overachiever streak triggered heart palpitations. I can never guarantee to myself or any founder that my investments will work. Knowing that, my choices are to either sit around and worry I am in over my head, playing at something I’m still learning, or trust that I’m creating exactly the experience I want to deepen my already rich expertise.
    Lastly, showing up as a woman with money comes with some hefty internal and external speculations. Did she earn it, did she marry it, did she inherit it? Do you know what the fundamental question beneath all of those speculations is? Does she deserve to have it? I’m sorry, but there is not one wealthy person on this planet who can prove they deserve to have money. But the fact that women are scrutinized by themselves and others for merely being in possession of it is a waste of time. The point is, we have money at our disposal, so what are we going to do about it?
    I’m an advisor to Stacks House, a financial pop up experience designed for women, and they cited a statistic recently that says in the next decade, the largest transference of wealth in our country’s history will place $12–40 trillion in new hands. It is estimated that two thirds of that fortune will be controlled by women. If there is one thing I have truly enjoyed about hanging out with men from the investing world, it’s that they don’t care how other men became rich, all that matters is that they have money, now. Whether you’re a woman who makes your own money, grew up wealthy, or shares assets with a partner or spouse, our culture supports women with money when we want to “treat” ourselves to things that represent kickass independence (I’m looking at you left hand diamond rings, every spa everywhere, all the fashion brands). Nothing wrong with them, and I absolutely partake, but when I moved into investing there was something more visceral about showing up in an arena where you are certifying yourself as having money, trusting yourself to give a stranger a giant check, and hanging out long enough in the banter and pissing contests to feel your metal.

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. :-)
Of course I would like to see more women become active angel investors, but if we are talking about what idea would bring the most amount of good to the most amount of people, I think that comes down to something bigger. I’d love to see all of us with privilege, especially women, learn to wield it in very different ways. We need to be using it for ourselves and for others at the same time.

When I say privilege, I mean access, connections, money, and advantage. These are all just tools. To me, it seems like the model of having privilege has been stuck in three options for too long: deny it exists for you and scramble for more, accept you have it and hoard it, or feel guilt and give it away. There’s some insanity in all of those approaches. Imagine you had a house that came with a really well-stocked toolbox. If you spent your life pretending you had nothing you could fix your leaking roof with but continued to amass more hammers and screwdrivers, you would be nuts. If you had zero carpentry skills but would not let anyone else touch your tools to fix your leaking roof, you would also be nuts. And if you felt horrible for all the people who didn’t have tools and gave your tools away while water dripped onto your head, you would be a kind, generous person . . . but you would also be nuts.

What I think is missing for historically disenfranchised groups, like women, who are coming into more privilege now, is this way of owning the advantages while also accepting the opportunity of privilege. To do that requires looking straight into the reality that you have privilege. It requires accurately appraising it so you can understand how to use it. It asks you to take a moment of gratitude for whoever helped cultivate this privilege for you, including yourself and your own hard work. It asks what you want from it, what will meet your own desires. And if you stop there, you will live a lovely, cushy, privileged life. But if you really want to take it to the next level and find some killer life satisfaction, you get to a place where you understand that privilege is power. And then the question is, are you going to deny you have that power, abuse it like others have abused disenfranchised groups you might belong to, or own it, knowing you can knock down some walls with it? I personally get off on knocking down walls.

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

“She wasn’t a person to whom things happen. She did all the happenings.” — Muriel Spark

This quote sums up how I aspire to approach my life. I look for and find my agency, because I always have a choice. That’s especially true because I have privilege and all the options that come with it. That’s not how most people on the planet get to live. So just as I show up to vote every Election Day because there are women in the world who would die for that opportunity, I also make a point of reminding myself that I get to design my life from my lens. I can move beyond reacting or becoming passive. If I want something to change, if I want to experience something new, I believe I am the best person to define and create that for myself.

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 have been moving into film producing and I want to keep the same focus on supporting female directors and writers. One person I would be beyond honored to have lunch with is Viola Davis. This isn’t just because there are so many things I admire about her, but because her production company, JuVee, is doing some really interesting things in both who they represent and how they work with investors. The other is Emma Thompson because I think she does such a wonderful job modeling how to leverage privilege on behalf of others while creating an incredible career for herself. I would love to talk to both women about what they see on the horizon for women in film, especially behind the camera.

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

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

Jason Malki

Written by

Jason Malki is the Founder & CEO of StrtupBoost, a 30,000+ member startup ecosystem + Flex5, a startup investor relations, marketing, and design agency.

Authority Magazine

Leadership Lessons from Authorities in Business, Film, Sports and Tech. Authority Mag is devoted primarily to sharing interesting feature interviews of people who are authorities in their industry. We use interviews to draw out stories that are both empowering and actionable.

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