A Seat At the Table

Don’t boycott controversy. Shroud yourself in it. Build a Trojan Horse and invade it from within.” – how can women get a seat at the table, even in controversial projects, in order to lead progressively and generate positive change?

1: Click

I was scrolling Slack one lazy afternoon when a provocative thread caught my eye. Sourcing was struggling to find a PM for a dating app… A dating app for people interested in explicit financial exchange as part of their relationship.

I blinked as an achingly predictable and borderline sanctimonious script unfolded. *Several people typing…* Uber for prostitution? No thanks. Gold-digging as a service? Ew. Not touching that with a 10-foot stripper pole. Ha, ha.

My cursor gravitated towards the ACCEPT button in the projects invites dashboard like a planchette on a Ouija board. What am I doing? I don’t have bandwidth for a new project, let alone the kind I can’t exactly write home to mom and dad about. My finger hovered precariously.


“The project is yours!” Slackbot pinged cheerfully.

Suddenly, for the first time in all of the 3 excruciating minutes during which I deliberated this decision, I felt calm. I marinated coolly in an oxymoronic puree of my own adrenaline and self-hatred for a moment. Then I proceeded to yawn, curl up into the fetal position, and take a deliciously procrastinating nap.

2: Flying toilets

Later that week, feeling well-rested and giddy with anticipation, I met with the client, “Gary.” Gary was an engineer and a pretty impressive one at that. He’d made a small fortune as an early Facebooker and founder of a successful data scraping company. I ruthlessly and unapologetically online stalk every human I ever meet in person, so none of this was new information to me. But as we inched our way down my usual slate of kickoff questions, I found myself relishing in the novelty narratives they unwrapped:

Gary wanted to build a clone of SeekingArrangement, the top sugar daddy dating site on the world wide web. He had been using the site for several months out of curiosity and couldn’t help scrutinizing every little user pain point in the product itself — the slow loading times, the outdated interface design, the bugginess on mobile, the poor image quality and resolutions. He was an engineer after all. I couldn’t help grinning as he said something very engineery at that point. “We could build a better version of this,” he muttered robotically.

“Well, there’s no question about that,” I countered, “Toto could build a flying luxury toilet, but the question is — should they?”

Gary’s eyes lit up as he went into his pitch: SeekingArrangement was generating an annual revenue of $80m since 2015. This was surprising to me because dating apps are notoriously not-lucrative. And in addition to SeekingArrangement, the founder Brandon Wade, ran an impressive buffet of similarly themed digital properties including MissTravel, What’sYourPrice, SeekingMillionaire. This Brandon guy was milking a herd of cash cows.

3: Don’t sugar coat it

Being the neurotic PM that I am, I had come to the meeting armed with an arsenal of academic papers, user interview transcripts, annotated screenshots and PR articles. As Gary’s pitch winded down, I took the opportunity to lodge several non-sugar-coated observations:

SeekingArrangement regularly runs PR campaigns promoting “sugar dating” as a lifestyle — a glamorous and efficient way for young women to pay off college debt, enhance their career by meeting successful older men, travel for free to exotic destinations. The messaging towards men positions SA as some kind of avant-garde charity organization through which men could do pro bono work as mentors, investors or patrons of the arts.

Some of the women I interviewed did use SeekingArrangement exclusively to seek out adventures with interesting, powerful men. Through this lens, the app struck me as a compelling platform that enabled socio-economic mobility in dating.

But as I surveyed the true power users of SA (active users who log on at least once a week and reported having more than 3 “arrangements), I saw a grim reality stripped of glamour and all those other fluffy, feel-good adjectives that initially lured users through the snappy signup flow. The majority of women I spoke to were being put in rather exploitative situations, where they were paid explicitly for sex, at rates slightly lower than what local escorts were advertising on sites like Craigslist. SA allows “sugarbabies” to state what level of allowance they want per month ($2k, $4k, $10k…) which gives the illusion of reliable, non-volatile income, but the reality is that the most common arrangement type was an on-demand, one night stand cash transaction. The most heartbreaking epiphany for me was that SA’s product messaging had strong-armed many women into believing that sugar dating was actually a valid way to be earning a living.

Needless to say, I found SeekingArrangement’s growth tactics and product design to be troubling from an ethical standpoint. “And in this case,” I segued, “I believe that bad ethics is bad – or at least stifling – for business.” If our goal was to build a better product, then we should endeavor to build one that felt a little less like it was architected by a penis.

Because ethics aside, it was evident that female users did not feel comfortable using SA. This in turn, negatively impacted the male user experience (high ghosting/abandonment-rate and unmet expectations.) A high female:male gender ratio is critical to retaining users on sugar dating sites, so it is in our best interest to ensure that female opinions and feedback are reflected in our product.

4: Incremental success

I have immense respect for the scrupulous attention Gary paid to each of my concerns. He echoed my sentiment around designing a product that empowers women and the LGBT community, who are often disenfranchised or exploited in online dating arenas at large. SeekingArrangement and other existing sugar dating sites are all male-dominated and operated; it is clear that the messaging caters to heterosexual men. We wanted our product design to empower vs exploit.

While we seemed to unanimously agree on most points at a conceptual and theoretical level, it took some extra greasing to coax Gary into adopting some of my more “progressive” product recommendations. Gary wanted to walk a more conservative path that deviated minimally from what he saw was a working proof of concept (SeekingArrangement).

For example, I proposed that we could expand our audience by downplaying the sugar daddy terminology. My revised pitch of the product was that all relationships are transactional, and Honeyjar simply enables users to be transparent about the things they want out of their dating experiences. SA focused purely on financial transactions within relationships. From speaking to users, it was evident that cash allowances were the least exciting and most stigmatizing transaction type for both men and women.

I argued that by expanding our interest prompts to include other things such as travel, dinner dates, jewelry, mentorship – things that are already deeply embedded in more culturally accepted institutions such as “marriage” – we could have broader market appeal with a more mainstream audience.

Gary was skeptical at first; too many options could distract or confuse users. Undeterred, I mocked up a signup flow laden with friendly emoji and tags that both female and male users submitted. Once he was able to visualize the recommendation, he agreed that this particular divergence from SA’s model generated a great deal of upside.

5: The battle I didn’t win

I didn’t succeed in pushing all of my recommendations forward. One of the recommendations Gary tabled had to do with the fluidity of roles. Traditional sugar dating sites assume that a user identifies exclusively as a provider (sugar daddy/mommy) or a beneficiary (sugar baby), and further assumes that providers are typically male and beneficiaries are typically female. I validated through user focus groups that this rigidity in roles perpetuated certain stigmas that made women more apprehensive about having their identities exposed on this type of dating app. Forcing a woman to self-identify as a “sugar baby” typecasts her into the very narrow and scandalous “gold-digger” character, thereby posing an immense risk to reputation.

My remedy for this two-fold:

  1. Avoid “sugar” terminology entirely. Instead of asking users whether they identified as “sugar baby” or “sugar daddy,” I recommended we allow users to select whether they were looking for someone “fun and interesting” or “successful and generous”
  2. Secondly, allow users to self-identify as both provider and beneficiary.

The things people want and need out of a relationship are custom to each prospective partner. A career woman might find herself attracted to one man as a beneficiary, and attracted to another as a provider. Society is inching towards accepting that gender and sexuality are fluid. Power dynamics between people will increasingly become preferences unanchored to gender. Technology and forward-thinking product design empower micro-evolutions that contribute to greater shifts in our social and cultural landscape.

Gary ended up implementing part 1 for the beta launch and tabling part 2 because he felt it would be too confusing for our first batch of users.

6: Will you be my co-founder?

A week after we launched the private beta of Honeyjar, Gary formally asked me to join him as a co-founder. Having worked so intimately on the product itself both as a designer and a PM, I had grown very attached to this thing we’d built. But I had inhaled my own product’s koolaid too deeply to ascertain whether I’d built a Frankenstein or a Wall-E.

I agonized for weeks over whether or not I truly wanted to be the founder of a “transactional dating” app or if my vanity was perhaps leading me astray. I came very close to accepting his offer, and even drafted a co-founder agreement that attempted to outline various contingencies that I felt would make me more comfortable with some of the ethical gray areas I was still struggling with.

Reading back on this document, it is apparent that I was still trying to convince myself that what we were building was actually empowering and not exploitative. I was stuck in a devil’s advocate loop with myself:

On the one hand, I was building a product that enabled men to pay for romance.

On the other hand, all relationships are already transactional. and we are simply using technology to offset some  of the mismatched expectations and unhealthy power dynamics which stem from the toxic ambiguity of not knowing what the hell someone really wants from you.

On the one hand…sugar dating.

On the other hand, we had decided to nominally not be a “sugar dating” site. We simply built an interface for people to communicate more transparently and straightforwardly about their expectations within a romantic relationship.

On the one hand, Silicon Valley has been exploding lately with punishing narratives of VCs using power to pressure women into reciprocating unwanted sexual advances.

On the other hand, many women I spoke to in user interviews explicitly sought romantic partners who could provide professional career mentorship or invest in their startups. These women fetishized the very power dynamic that is being unequivocally vilified by the tech community.

I ended up rejecting the co-founder offer, but agreeing to continue guiding product development efforts as an advisor.

7: Haphazard conclusions

Are there aspects of the product that I still struggle to reconcile with my own moral compass?

Absolutely. As I reflect on the decisions I made from the haphazard click that landed me this project to walking away from the co-founder equity, I am reminded of when Elon was pressured into withdrawing from Trump’s advisory council. I felt strongly then, as I do now, that when presented with a chance to sit at a table alongside people you may not always agree with, or (in my case) work on a product that has the potential to exploit vulnerable women, it is almost our duty to seize these opportunities.

It is important to be honest with ourselves about the realities of current affairs and history. Sugar dating sites already exist, and will continue to exist. They have for decades; before SA there was Craigslist, before the internet, there were paper ads, street walkers, and French courtesans/pampered mistresses who didn’t mind getting naked for some extra dress allowance. Regulating sex and the way people value a romantic transaction has never yielded the results legislators intend.

Best case scenario, Honeyjar is a hit success and cannibalizes the userbases of all the other seedy, shady sites on the market by listening to its historically underrepresented female users to build a product that is ethical, that empowers its users, and makes dating great again. Worst case scenario, Honeyjar dies, and Brandon Wade goes on spewing the same silly stuff he always has while profiting from misguided, vulnerable women all over the internet.

Over the past year, I have attended zero rallies. I have made exactly zero political posts on social media. I have made zero comments on political posts. Instead, I’ve been building and advising Honeyjar. Why? Because I think it’s irresponsible not to be involved.

As an advisor to Honeyjar, I am in a position to influence the design and messaging of a product that has the potential to both exploit and empower women.

8: The table of ill repute

What’s the takeaway from all this?

I don’t know. Mainly, I wanted to process and document my own experience of building a financial dating app during this Era of Prolific Sexual Harassment Lawsuits/Exposes. I’m not sure there’s one clear lesson to neatly package and takeaway because this story spans so many shades of grey.

I’m not going to pretend that subverting an industry that historically exploits women was my agenda when I first accepted the project.

I took the project because curiosity compels me to examine controversial ideas under a microscope. I took the project because the words “wrong” and “evil” are trigger words for my contrarian ego. When people use those words to assert an opinion, it usually means they are launching a critique but cannot offer any constructive recommendations. They have neglected their responsibility to understand the context, nuances, and realities of a situation before articulating their judgment. Finally, I took the project because I would always rather be a player in the game rather than a vocal dissident from the sidelines.

That said, here are some of my own personal takeaways:

  • Don’t boycott controversy. Shroud yourself in it. Build a Trojan Horse and invade it from within.
  • Never let principle get in the way of progress. Don’t let rigid moral codes blind you from seeing where realistic improvements can be made to an unacceptable status quo, and seizing any opportunity to make incremental impact.
  • Sit next to the people you understand the least, if only to sabotage your opponent’s agenda through political or social maneuvering. Example
  • When it comes to driving real results, it’s more effective to have a seat at the table of ill repute than to preach to your own choir at the church across the street.

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