Emma Tessler, COO of Dating Ring

By Emma Tessler

Pitch events are some of the most nerve-wracking experiences. A room filled with high-powered investors who could fund your company and make all your dreams come true, if only your 3-minute pitch is compelling enough. And your schmoozing is schmoozy enough. Add an open bar and many companies trying to accomplish the same goal, and they are basically my nightmare. At one such event, my co-founders and I split up to cover more ground, and off I went, business cards in hand, to try and convince people to promise us money.

Near the open bar, I saw an investor whom I had greeted earlier in the day. With a beer in hand, he seemed pleased to talk with me again.  I immediately launched into all the amazing things our company was doing and why it would be a huge mistake to pass up the opportunity to invest in us. He was extremely friendly and excited about my pitch. He also lived in New York, and we bonded over the cold weather that we’d both be returning to once we left San Francisco. He suggested that, once back in NYC, we should get a drink. In fact, we should get drinks all the time! I chalked this up to the schmoozing portion of the event, and laughed.

He put his arm around me. And while most one-armed hugs result in a hand resting politely on your ribcage, his hand found his way to my — and I wish there was a better word for this — sideboob. Then he said, “You know what? I’m going to invest $50,000.”

There it was. The first offer I had gotten, and his hand was on my sideboob. For those of you playing along at home, that’s a man in a position of power, wielding his power by offering me money, and touching my breast.

Of course, this is all in hindsight. In the moment, my thoughts went something like this: “Whoa is his hand on my boob? What the hell? Oh Jesus it’s still there. He must not realize how far he’s wrapped his arm around. Yeah. What an awkward mistake to make.”

Now I understand this is insane, because sideboobs feel nothing like ribcages. No one stands there with their hand on someone’s breast, even if it’s the side, and doesn’t realize it. I thanked the investor for the offer and told him I’d have to discuss it with my co-founders, as I extricated myself from his arm and went to find them.

My two co-founders, who are also women, were standing together. I immediately blurted out: “Some guy just touched my sideboob! For a pretty long time! But he offered us $50,000!” They stared at me dumbstruck. “What the hell?” they said. I immediately felt stupid for telling them and making a big deal about it. Operation Downplay went into effect. “Yeah, but it’s not a big deal. I mean, it was only the side. $50,000!! That’s a lot of money!”

And $50,000 was a lot of money. It was the money we needed to hire another engineer, to jumpstart our seed raise. It was an investor who would be a good signaler, who could help to get other investors, and other offers of $50,000, on board. It was money that would have allowed my cofounder and me to pay ourselves a salary this past summer when we were relaunching our product, and had to forego salary so that we didn’t have to lay off any employees.

It was a big decision to make, and I couldn’t stop questioning whether I was exaggerating what happened, or being too sensitive. But my cofounders immediately assured me that that wasn’t the case, and that we could not take the money. They said it was ridiculously inappropriate, that our relationship with him would only get worse, that we should hold out for better investors to partner with.

And so the next day, I sat down and wrote the investor an email. I told him that while we appreciated the offer, we were being very strategic about which investors to partner with. It felt pretty gutsy at the time, but since time has passed, I couldn’t be more confident about the decision.


Emma Tessler is a matchmaker and the COO of Dating Ring. Emma studied Sociology andAnthropology at Guilford College before beginning her work as a sexuality specialist. In addition to creating a Teen Pregnancy Prevention Program, Emma has taught sex ed, led workshops, and counseled adults and children surrounding issues of sexuality. Since becoming a matchmaker, she has made thousands of matches and keeps track of all the couples via Post-It notes on her desk. Emma enjoys playing geography games, positing new theories about modern courtship rituals, and discussing her favorite dinosaurs. She hates writing personal bios for websites, but ah well. You win some, you lose some. Follow Emma on Twitter at @EmmaTessler.

8 Responses

  1. Paul Johnson

    Thanks for sharing. Sorry to hear you had to deal with such behaviour.

    I think you did the right thing, not just because such behaviour shouldn’t be encouraged, but because you couldn’t possibly have a straightforward working relationship with such an investor.

  2. Shay

    Good for you! $50,000 is a lot of money, but your dignity is worth so much more. Don’t even get me started on alcohol at events like this, its just a bad idea altogether. And good for your co-workers for not letting you just brush it off!

  3. Lucas

    That is so disgusting.
    It’s amazing how people can abuse their power just to have sexual favors.
    Had you accepted the money probably in his mind he would have the consent to abuse more and more.
    What is sad about that is not only you’ve been to this awkward situation (at minimum), but he also got away like if he had done nothing much. It’s still an harassment!

  4. Katy

    $50k to touch a side boob? how about $100k and anyone can touch both of my side boobs!!!

    Really, a fool and his money are soon parted!

    Wow, a lot of fuss about nothing!

  5. Ashley

    Frankly, it’s embarrassing for the private equity community that characters like this aren’t unusual. But fortunately they aren’t all that way! Good on you and your team for learning to spot the bad eggs and for not pursuing that deal!

  6. A Man

    I applaud you for not taking the money, but I think that a better approach would have been to loudly say “WOULD YOU MIND TAKING YOUR HAND OFF MY BOOB PLEASE?” right then and there, so that as many people as possible hear it.

    Telling him you were being strategic about which investors you go with is very diplomatic and non-offensive and doesn’t burn any bridges, but the problem is that this pig hasn’t larned his lesson – he thinks you’re being strategic about investors – it hasn’t occurred to him that you were being diplomatic and that it’s not OK to grope you. He’ll probably try it again, and the next girl might not be as strong and might take the money. Embarrassing him in a room full of investors might have stopped it from happening again.

    All the same, good on you. 🙂

  7. Dani

    Thanks for sharing, and wonderful to hear you have smart, savvy cofounders who support you in what was definitely the right decision. Agree with Paul — not worth entertaining someone’s delusions for the rest of your working relationship. I’m all for a well-timed “Excuse me, are you touching my boob?” but doubt I would have had the guts myself in the moment.