My advisor would not take no for an answer

Sexual advances from potential investors pose both professional and emotional doubt and frustration. How can entrepreneurs handle and overcome such behaviors coming from superiors?

What happened?

When I first came to San Francisco, I was inexperienced and seeking mentorship. I had a project that I was working on at the time, seeking funding. A respected venture capitalist was introduced to me and asked me to meet at a hip SF spot for drinks after work. I hadn’t been there before and was looking forward to meeting him. When I arrived, the VC quickly pivoted the meeting into more personal terms. I became hot in the face, and tried to gracefully avert his advances, but also felt conflicted — Was this normal? Was I not a good investment? Was this within his human right of self-expression as someone who I wasn’t in a formal business relationship with me?

We had been introduced through a mutual friend, hadn’t talked about the purpose of the meeting much, and, besides, several of my friends were successful businesswomen in consensual and healthy relationships with venture capitalists… perhaps I entered into the meeting with bias, seeing him for only his job, and not as a complete human being who had just been introduced to me without a clearly stated agenda. Was this why it was harder for women to fundraise or was it hard for me to fundraise for another reason and I wanted to find an excuse?

My company wasn’t raising money successfully, and he was intelligent and experienced, which I respected. He had a lot of great qualities and was quite funny. I decided to continue the conversation with openness to different possible outcomes — we spoke about a range of topics and had an enjoyable night. I felt simultaneously disappointed in the lack of business progress and interested in getting to know this person more, despite having my guard way way up. At the end of the night, he planted a kiss on me. I was taken aback, thanked him for his advice and excused myself swiftly into my waiting car.

We texted back and forth and several weeks later, the VC invited me to join him for a night out. I graciously declined, but maintained casual conversation. After multiple invitations, I decided to be open to the direction of the world, decided not to pursue a professional relationship with him and agreed to meet him for date. We dated for about six months. Later, we ended things when I found out the relationship had not been monogamous, despite his adamant requests for a monogamous relationship with me. I asked him for a bit of time, and we scheduled a friendly dinner two months out to reconnect after the dust and the hurt had settled.

Over the course of several years, we stayed in touch and became close friends. He was intelligent and became somewhat of a sounding board for me during my early career. In part, because of our history, he became emotionally invested (if not professionally so) in my success. He introduced me to colleagues who became important pillars in my career. He helped springboard me into other relationships that became important to my success. This grey space was hard to classify—it never felt black and white, but he cared and was helpful and I enjoyed having him in my life. I cared about him, and counted him as a close friend.

During those years, I had started a business that was starting to look like it might become quite successful. He got more and more excited about the project and asked to be made a formal advisor, citing the impact he’d had on my career and his ability to further my network. He told me he could be a real asset, and could fight for the success of my business. I was honored to have him responding so enthusiastically about my work—this is what I had wanted all along!

I weighed the pros and cons — startups are about evaluating risk more than they are about completely avoiding it. In the end, I felt having him involved would be our best chance of getting this thing off the ground. Besides, we had been friends for years, he was about to propose to another woman, and had not had a romantic relationship of any sort for a long time. I explained this to him and made it extremely clear that this decision would mean that we would never be romantically involved again. He agreed, and I agreed. We shook hands and slapped each other on the back.

As the months passed, and the business starting looking more compelling, he began pressuring me physically and began telling me he felt conflicted, was sorry for cheating, and felt he had made a mistake. I told him I cared about him, told him he was important to me, and tried to let him down with compassion as I averted and brushed off increasing advances. Always central to these conversations was how much I cared for him, how important he was, and how much I respected him—that I wanted to build something valuable in the world together, and that we’d moved on to new chapters. I reminded him that we were better off as friends and colleagues, that he had a great relationship with another woman that he was jeopardizing through his behavior, and that we could stand to be very successful together. I reminded him that we had failed as romantic partners and agreed, in good faith, upon entering into a professional relationship, not to revisit those avenues.

When the business appeared to be poised to get its first round of financing from top-tier investors, he started calling me for late night “urgent” pitch meetings, telling me my pitch was not ready. I believed him when he told me loudly that he would be embarrassed if I gave the pitch the way it was. I do look back on those old pitches, which looked so very different from the ones I give today, but it was hard to separate the likely genuine feedback from my desire to stop the advances altogether. It became impossible to get advisory feedback without feeling like I putting myself in dangerous and increasingly pressured positions. He used those opportunities to try and physically coerce me into staying the night, trying to prevent me from leaving on multiple occasions, always with a faux-joking undertone. A hand on my leg, a kiss on my cheek that came a little too close to the corner of my mouth, an effort to push me down on his couch and stick his hands up my blouse.

I felt trapped, I questioned my own value, and I felt that cutting ties with him at the start of our raise had the ability to cast doubts on what was shaping up to be a potentially successful fundraise. I was afraid that if I cut the interactions I wouldn’t get the practice and input I wanted and that he’d be right, and I would embarrass myself. Again and again, I rebuffed these advances, always seeking a way to let him down kindly, but increasingly felt that I did not know what to do. I knew that a respected VC exiting a company during the beginning of a raise could often be a negative enough signal to prevent the company from closing financing altogether. I thought if he backed out right now, we would not raise the money we very much needed to continue building something important.

As I was leaving after one of these meetings he gave me a key to his home and pressured me to accept it. Confused, I silently pocketed the key, and left. I called him the following day, asking for clarification—I was dating someone else and living with them at the time, but this person and I had been close, and sometimes ran errands for one another—was this a key for logistics? He clarified to me that this was a key so that I would not continue staying with the man I was dating and would instead stay at his home while he was away traveling. He told me he wanted to be with me and said to me, “I just want to know how happy I should be for your success.” I asked him if he was implying that the key was an offer to move into his home, and he confirmed. I was mortified at having led him on by taking it, apologized profusely and had a courier return the key that day. He texted me telling me that he thought I’d cared about the company, and now believed I wasn’t really committed.

The situation came to a head one night a few weeks later at an event thrown by mutual friends as he cornered me and emotionally poured out to me that he felt I was “pregnant with our baby.” The next day, I found him, sat down, and told him I would never be able to marry him or have a family with him. He cried and I held him until he stopped.

Embarrassed and feeling responsible for my situation, I did not tell anyone what was going on, but continued trying to navigate on my own. I started only meeting him at busy cafes early in the day (often he would get busy and try and arrange to meet at the end of the day instead), and I stopped picking up calls after five. He began sending me texts, stating that I was unwilling to take feedback and was on a sure-fire path to failure. His texts became more and more angry and assertive.

I remember crying myself to sleep, wondering if the only reason anyone had an interest in my work was ulterior motives, and wishing over and over that I had been born a man, so that I could be a part of the intellectual conversations, advice, and growth without these advances. I cried until my eyes hurt. I cried until my face swelled up and I looked awful.

Next, he called my co-founder, accused me of fraud and incompetence, and asserted that both my partner and I would be un-fundable in our current state. He kindly volunteered to take over the company as interim CEO to ensure my co-founder didn’t “get in trouble” while “protecting me” by reserving marginal stock for me on my behalf.

That same day, a female customer reported via text message to me that he had been inappropriate with her during a meeting by touching her under her skirt. I went to my then co-founder to break the news to him and we ended up phoning the advisor together. Under the pressure and conflicting assertions, my co-founder buckled and quit.

How did you respond?

I came clean to my other team members, and asked them for advice and help. They reassured me, pumped me up, and stated firmly that they would only continue on at the company with me as the leader—they were clear that they were here because of me or not at all. I felt respected; I felt gratitude; and I felt like I had a way forward. I sucked it up, and we came up with a plan of action.

After failed attempts at direct resolution and negotiation, I notified the man’s investment partner of the situation (at least in broad strokes). I received a written resignation from the advisor and then worked with my team to have this man removed from my company for a marginal fee (less than $30, plus legal fees for the agreement to go our separate ways). He nitpicked the negotiation and dragged it out, but it eventually concluded, much to the joy of our team.

What were your takeaways in hindsight?

I learned that I should have trusted in my team members much sooner, and should have let them know what was going on. I am so deeply grateful to the three people who helped me navigate this and only wish I’d had the courage to tell them—and to take action—sooner. I was far less confident than I am today, but I try to cut myself some slack and remember that I got here through the school of hard knocks—it’s a part of who I am and a part of what made me stronger.

These lessons are often, unfortunately, only learned through experience, and so, I’ve also learned to give myself a break about what happened. For a while I felt bitter, but I’ve learned to let go of that too because it was harming me more than him. There is no use focusing on feeling wronged when there is so much right that can be done in the world! Where we focus our energy determines whether we move forward with our goals, and I’d rather go forwards than backwards.

My company has gone on to raise over ten million dollars from leading investors who are respectful, helpful, and offer support (without unwanted advances!)—and we have been able to carry forward with the best possible team. I have learned that the best way to counter his negativity, is simply to succeed and focus my energy on making my business successful. I’ve learned that the #1 most important factor for any close relationship in life, business or personal, is the amount of respect that you have for one another.

No person is important enough for you to put up with this type of behavior! Anyone who acts this way should be notified that their behavior is not ok and be replaced quickly because they are a liability—not just to you, but to the organization as a whole. Chances are, if you’re successful, you’ll be working together for a long time, so make sure you’re only working with quality people.

Without realizing it, my lack of action had endangered other women whom the company was beginning to do business with. While that spurred me to action, I would recognize now that if someone is displaying this type of flagrant behavior towards me, they are likely doing it towards others. I was less aware of this and felt that I was to blame. Blaming myself prevented me from recognizing the bigger picture and acting as a mature CEO. I learned that self-blame is often limiting and prevents us from acting as our most powerful selves. By blaming myself less, I could see more clearly what needed to be done and the risk that existed for others.

I hope sharing this story can help anyone else navigating a situation such as this to know that they aren’t alone, they are likely good enough on their own, and they can overcome the situation. While I don’t like to take joy in the suffering of others, I do occasionally remind myself that, for his actions, FOMO was the best punishment of all.

Watercolor by Charlotte Goff

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