All the Possibilities of a Pitch Performance

In 2018, Forbes would have published this article, if I had agreed to write a few articles a month, pro bono. With an already full schedule, I had no time for hobby writing and declined.

“Welcome to ladies’ night!” the event host greeted my friend and I enthusiastically. We all laughed. Yet, in the pit of my stomach, the greeting felt like an all too familiar, awkward reminder that I was, yet again, somewhere I did not belong. Looking around the ballroom, I spotted four other women mingling in a crowd of about 80 attendees.

The investor luncheon was a gathering of a ‘diverse’ group of investment and industry professionals who came to hear a fundraising pitch from an early stage start-up. A female entrepreneur friend had invited me as her guest. The event host had told her he wanted to encourage more women to attend these events and asked her to bring female guests. By going, she assured me that I’d be doing her a favor, keeping her company, and him a favor. Besides, she added, the host had waived registration fees for women:  hence, ladies’ night.

Over a year ago, when I was still pitching my startup - a software platform for global O&G companies to source qualified, local suppliers in emerging markets - I had walked into rooms like this countless times. Amped on adrenalin, continued progress and big ideas, I had hoped to conquer a few hearts and minds while learning a few things in the process. Unlike when I first started out as an entrepreneur in 2014, today, I saw clearly that I was, indeed, an oddball. The room was over 90% men, and the vast majority of them were over 50. Based on my experience as a 30-something female entrepreneur in the oil and gas (O&G) industry, including as a frequent event host and attendee, I knew the types of deals this industry crowd would be interested in hearing about, and I knew the types of technical and financial questions they would ask.

Without the excited buzz of limitless possibilities consuming my mind, I entered the event room today intensely aware of the maleness, the whiteness and the gray-hairedness of the audience. In years past, when I had been fresh-faced and not-yet-ingratiated into the world of deal making in the industry, my head was swimming with ideas and solutions to gnarly policy issues and complex business problems. Undeterred by outsized obstacles, I wanted to change the status quo. I wanted to make big business a better, more efficient corporate citizen. I wanted to operationalize corporate social responsibility (CSR) with a SaaS platform for supply chain and compliance, which I believed could move CSR from being a cost function to a business imperative. I never imagined that ‘my looks’ would factor so much into the equation.

Today, acutely aware of ‘my looks,’ the recurring thought in my mind was: “I don’t belong.” It took years of feedback, explicit and implicit, for me to arrive at this conclusion. Of course, if I had simply looked around me and realized how important it was to look the part, I may have arrived at this conclusion considerably sooner.

The entrepreneur pitching at this luncheon reminded me of myself, in ways. The way he spoke, for example:  he sounded like he had a lot on his mind. I assumed he was mired in data and information on markets, customers and technical research, overwhelmed by the endless possible directions his start-up could go and struggling to balance and incorporate the plethora of opinions on how best to confidently present his strategy and financial projections. I assumed that, like me, he knew that his objective was to convince the audience that he offered a viable, future, previously-untapped source of revenue.

More important than his technical expertise or his facts and figures, in this room, he needed to exude a supreme level of confidence. He needed to convince prospective investors of one concrete fact – as concrete as the foundation of the building we were gathered in: that the one small barrier preventing him from generating millions or billions of dollars for them was their multi-million dollar investment in him.

Although both our start-up ideas were big and involved changing the industry for the better, the mere fact that industry investors were paying to hear his pitch, tacitly confirmed that he was more readily well-received and approved by the boys’ club than I was.*

Beyond the tacit approval from the industry that this pitch opportunity conveyed, so early in his start-up journey (arguably, pre-maturely), one of the other most glaring differences was his physical appearance. How I dressed and presented myself was a hot topic when I was pitching my start-up, by my recollection, the most popular one.

Not one to prioritize fashion, as an entrepreneur I simply prioritized looking professional. I considered my brand-less, nondescript style to be “business casual.” Colleagues in the industry had a different opinion. Ironically, it took becoming an entrepreneur in the male-dominated O&G industry to realize just how critically important fashion is to men. A male friend and colleague in the industry, who had countless times commented on my preference for comfy, flat black shoes, summarized my style best in one word, using a tone of voice that expressed both his disappointment in my lack of showmanship and his admiration for the way I think: sensible.  

While his commentary on my style was, at least in part, supportive, other professional encounters and comments on my appearance, collectively and individually, proved just how challenging it was to be taken seriously as a female entrepreneur. After I delivered a well-prepared presentation to a business partner, his first comment was that I wasn’t wearing enough make-up; his advice, if I planned to deliver the same presentation to more people in the industry, was that I needed more make-up. Within the first half hour of a first meeting with a prospective client, he made at least six comments, including comments on my appearance, that were reportable to human resources, had I been an employee at his company. As an entrepreneur, such checks and balances on behavior do not exist. There were no HR protections. It was the wild wild west; anything goes. Despite the discomfort and convinced that I could manage the situation professionally and even turn it around, I continued to meet with him in hopes of landing a big deal with his company; but, he insisted all subsequent meetings be over drinks at bars. Over many months at these bars, he made countless business promises that never materialized. 

When I met with a prospective investor/client, who I was introduced to by a mutual friend that was confident I’d receive either seasoned advice or constructive criticism about my product and business strategy, the most direct feedback I received was that the color of my purse didn’t match the color of my pants. Abroad, I was told I needed to wear a wedding ring to indicate I was already “taken;” otherwise, businessmen were unlikely to invite me to the after-hours drinks or dinner meetings, where all the business deals were made. Apparently, unwed women were socially threatening and, naturally, risky, untrustworthy business partners. 

In each of these situations, at the time, I managed to find humor in the absurdity (and misogyny) and forge ahead, both with my start-up and cultivating the relationships. Yet, ultimately, these comments were not funny. Combined with other unfavorable timing issues in the industry, which would require an entirely separate article, they directly contributed to my startup’s “death-by-a-thousand-cuts.” 

If my style was sensible, the entrepreneur on stage at the fancy pitch event could be described as disheveled:  wearing a wrinkled button-down shirt, no tie, casual business slacks, eye glasses and a messy mound of curly hair. Beyond all the time he had saved by not putting any effort into what he wore, I calculated that, because he hadn’t spent any time doing his hair or his make-up, he likely had an extra 45 minutes to review his pitch deck and rehearse his presentation. In the start-up world, 45 minutes often feels like it could make or break you.

At the height of my entrepreneurial hustle, critiques on my appearance hadn’t bothered me, at the time. After all, my priorities and vision were bigger than small-minded comments. But, sitting in the audience of this pitch performance, I couldn’t stop thinking about how, had I been the one pitching my startup or vision for innovation in the industry, my appearance and style would have been considered more important than anything I could have said. Certain that not a single gentleman in the audience would be offering this male entrepreneur any feedback on his lack of fashion sense, color coordination, social-status-statement jewelry or make-up, I seethed quietly in my seat.

As I listened to his early stage business idea, I both empathized with him and judged him harshly. Unlike other exceedingly confident entrepreneurs I’ve heard pitch, this entrepreneur was not just chasing dollar signs: he was clearly intelligent and pitching a sustainable business concept. He was solving a resource problem, and, if the business proved viable, it could yield environmental benefits over the long-term. Beyond his obvious talent and generous ambitions, he demonstrated strong technical expertise on a rather niche geotechnical topic. His pitch demonstrated his expertise and capabilities well. These were all good things.

What floored me was his audacity. In this day and age, early stage startups are expected to have achieved proof-of-concept or traction; at least, these were the expectations all investors had had of my startup. With merely data projections and a dream, he had the audacity to ask a roomful of established investors for $15 to $20 million dollars, merely to prove that his ideas could eventually generate profitable revenue. In other words, he was not asking for a multi- million-dollar investment to build the solution that would immediately start generating returns. He was merely pitching a sophisticated, data-driven version of a “back of the envelope” drawing: the types of whiskey-soaked envelopes that, a decade ago, (male) entrepreneurs would brag about getting funded over a few drinks and a solid handshake. Without calling it what it was, he was asking for a multi-million-dollar proof-of-concept investment, from a roomful of strangers. Even for the high-risk-taking investors, who had paid to hear his seed funding pitch, they were unlikely to fund such an ask without proof-of-concept.

Even though he didn’t know what his technology would look like, or even who, technically, would own the IP rights, or whether the physical infrastructure would be economically viable enough to bring the solution to market, he assured the audience that, because he thought big and ran fast, it would all work out. Somehow, he had been invited, all the way from Canada, to come pitch to these Texas investors, before having done the hard work. Meanwhile, despite having done the hard work and having strong connections in the industry locally here, I was never invited to pitch to investor groups like this one when I was seeking funding.

When I was in his shoes, before I had built a prototype or proven any concept, I literally had to pay people to listen to me. Whereas, he is the headlining speaker at a luncheon that people paid $50 to attend. Whereas, with the tens of thousands of dollars that I needed to get my start-up moving forwards, when investors talked to me, they gave the impression that I was a charity case. They would say things like, “I’d like to help you,” instead of: “What is the business case?” or “I’d like to invest in your business.”

Although neither of our start-up ideas offered a risk-free return on investment, an investment in my start-up would have been considerably less risky. At the same stage of our start-ups, an investor could have given him $20 million and lost everything, or given me $20 thousand and lost everything. Having already received more tacit approval from the industry than I had at such an early (arguably, premature) stage, an investor might consider our overall risk levels the same, even though my ask was a mere 0.1% of his.

The imbalance in perception, opportunity and privilege glared me in the face. Far too many days in the O&G industry, I'd felt like I didn’t belong. But today, the fact that I didn’t belong felt intensely personal. I knew the thoughts he was thinking and the risks he was taking. I knew what it was like to prepare for and pitch to these types of investors. I knew what stage he was at with his start-up. Not only had I been in his shoes before, but, despite the facts I had done all the hard work that still lay ahead of him and had results to show and that I was an insider locally, the door to pitch at private events like this was not once opened for me. Today I realized that, despite meeting all of the expectations industry insiders had shared with me (except, of course, wearing more make-up, jewelry and higher heels), I remained an outsider. 

The trials and tribulations of scrappily building and testing a software product included many twists and turns, like being swindled by service providers and misled by interested customers and investors. Each time I failed or went down a dead-end path, I picked up the pieces. Eventually, to continue funding the start-up, I went into debt. Despite overcoming all these obstacles and earning my “street cred” as an entrepreneur, I never secured the million-dollar investment my start-up needed to continue to grow.

Throughout this particular event, I had been talking with a wealth management advisor sitting next to me. At one point in our conversation, after learning I had been an entrepreneur, he enthusiastically asked: “Do you believe anything is possible?” The question was so broad and big, he may as well have asked “How do you define the universe?”

I sighed, took a breath, and replied “It depends.” Noticing his disappointment, I explained that I believe there are no limits to ideas, innovation and the human capacity to endure. But, I believe that, as human beings, we put finite limits on all these things due to our own limitations. The systems we create, the norms we perpetuate and the unconscious biases we remain blind to.

When I think about the possibilities for my start-up, I remember what an initial business partner, a seasoned executive in the industry, had told me soon after we first met. He said he was excited about working with me because he just knew - he was absolutely confident - I would be successful. He saw a future that was bound to be successful. A few months into our partnership and after months of asking him not to call me “cupcake” and other terms of endearment that didn’t reflect our relationship, at all, he ultimately admitted that he had really hoped we would be friends and hang-out. At the end of the day, despite his belief in my vision and the decades of seniority he had over me in this industry, his primary interest in working with me was the pleasure he thought I could bring into his world. I would have rather been called “bossy” or “bit3hy,” because at least those names would have suggested he took me more seriously.

Today, the possibilities for women leaders in male-dominated industries continue to be limited. Well-meaning intentions, like “ladies night” and offers to “help” women entrepreneurs are seemingly nice offers that, at the end of the day, don’t mean business. When women are (unconsciously) believed to exist to provide pleasure or radiate beauty, they do not receive the same respect or serious consideration as men. What I wore, whether or not I smiled and my marital status should not have factored into a single conversation with prospective clients and investors. Yet, far too often, they did, and, each and every time, those comments diminished the talent, knowledge, vision and solutions I brought to the table.

Often, women like myself are told that we are asking for too much or offering too little. When in fact, the entrepreneurial world quantitatively shows us, in pitch decks and research studies, that male-led start-ups often ask for more (read: too much) and are a greater ROI risk (read: offer too little). Our existing system perceives men as having more potential than women, and it rewards them financially for this perception, not actual outcomes.

One day, I hope to attend a pitch event and instinctively know that I belong. I hope there’s no longer a need for “ladies’ night” at investor meetings. I hope I am not called “cupcake” or “bossy” or “intimidating” by colleagues again. I hope to be seen as the investable, tough-minded, respectable professional I am and not expected to be a source of pleasure or an icon of style. When those days arrive, I will finally believe anything is possible.

Footnote:

*In fairness, one reason his start-up was better received by the industry was that it dealt with extraction processes, whereas my startup addressed business and supply chain, or rather, non-technical, issues. Generally speaking, industry investors at that time tended to be more interested in below-ground technologies.