Raising capital is hard for everyone and much has been written about the unique challenges faced by female entrepreneurs. I started my first tech company, Posse.com in 2012 and I pitched it hundreds of times before I closed a round of funding. I remember hearing vague complaints in the news about women who’d been propositioned for sex while raising investment and I couldn’t imagine it happening to me. Every investor I’d met with had been polite and respectful.
Then it happened. It was two years into my journey as a founder and I was raising a small round to help facilitate our merger with Beat the Q. I met Mike in New York at a tech event and he visited Sydney some time later. This extract from my book is the complete story of our exchange on the night he agreed to invest noting that I’ve changed the name and identifying features for legal reasons.
To any woman has had a similar experience, I apologise for not writing about this earlier. At the time, I wrote a high-profile column and I should have shared my experience. I kept quiet because I felt ashamed. I wondered if, by going to a restaurant at night and engaging in friendly conversation, that I’d led him on. I hadn’t.
I now feel embarrassed at my polite response. I wish I’d reacted with outrage but I felt shocked, horrified and I didn’t know what to say.
We must call out obnoxious behaviour, even when it isn’t criminal. We must share our stories and arm each other with the knowledge and insight to respond powerfully in the moment.
The below extract is from Rebekah’s book 138 Dates, out now through Allen & Unwin and available at Booktopia and all good bookstores. The book is the true story of Rebekah’s search for love and happiness while at the same time raising capital and building a technology business. The book features advice from a therapist and well known friends including investor Bill Tai and Canva’s Melanie Perkins and Cliff Obrecht.
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Tonight I’m meeting Mike at Rockpool Bar & Grill, an upmarket restaurant in the Sydney CBD owned by celebrity chef Neil Perry. Mike is a businessman from Manhattan who invests in startups for a living. He has white hair, a pink scalp and walks with his legs apart to accommodate his round belly. Tonight is a final ‘getting to know you’ dinner and I’m hoping he’ll give me good news. I really need good news.
I first met Mike at the NY Tech Meetup, where he handed me a card. ‘I can see there’s a lot of people waiting to talk to you. Here’s my number. Reach out if you’re looking for investment.’ I emailed him the next day but didn’t hear back. In my final week in New York, I tried again.
‘Rebekah!’ he replied. ‘I wondered what happened to you. I’ve been using Posse.’
We met at his one-room office near Central Park. A stack of framed sports posters lay propped up against the wall. I expected Mike to be slow, like his appearance suggested, so I was surprised at his sharp and thoughtful questions. He knew a lot about other Australian companies. ‘Wow, you know the Canva guys. Can you introduce me?’
I asked how he likes to work with companies he’s invested in. ‘I’m very hands off,’ he said, reclining in his seat. ‘I back people who I think are smart. Then it’s up to them.’
‘And what’s your standard investment size?’
He swayed his head from side to side. ‘A hundred K. Sometimes two hundred. It depends on the opportunity.’
‘I’ve got four hundred already committed in the round,’ I explained. ‘I need one-hundred more to close.’
‘What’s your monthly burn?’
‘Seventy-eight. It mostly goes on wages. We’ve got a really strong tech team.’
‘And how much have you got in the bank?’
‘A hundred and ten.’ I looked up, feeling my eyes drop open like a puppy pleading for dinner.
He inhaled slowly through his teeth. ‘You know what, I’m coming to Sydney in a few weeks. I’ve got some business to do down there. Let’s meet again then. I’ll visit your office.’
‘Sure,’ I said. I’d rather you just say yes now. ‘That would be great.’
Yesterday I walked Mike through our Surry Hills office. I introduced him to Glen and the engineering team, to Jen and to our new graphic designer Anna. We’d sat at the Pieno café on Crown Street and I’d shown him the presentation again.
‘This is exciting,’ he’d said. ‘I can see where you’re going with this. Well done.’
I step into the grand dining room with marble pillars that look like the entrance to a courthouse. Mike arrives, leaning in to kiss my cheek, and a waiter shows us to our table. We pass an open kitchen where men and women in white shirts and chef hats toss food in frying pans and serve up plates on a clean steel bench under heat lights. My seat is on one side of a long bench. Mike is on a black chair opposite.
He examines the menu. ‘Do you mind if I order for the table?’
‘Of course, I just don’t eat —’
‘Seafood okay?’
‘Great.’ I smile in relief.
He holds up a finger to the waiter, pointing to the wine list: ‘We’ll have a bottle of the 2005 Bollinger ‘Grande Année’ Brut.’ He smirks at the jaggedness of his bad French accent. My eyes scan the list. $890! I could fly to New York for that.
His eyes crease as he sinks in to the menu. The waiter returns, cracking open our champagne like it’s no different to a $20 bottle and I imagine the faces of 890 children in Africa who could have eaten today.
‘Cheers,’ he says, raising his glass. ‘Since we’re celebrating.’
‘Celebrating?’
‘My investment in Posse.’ He smiles. ‘I’m in. Put me down for a 100K. Send the paperwork tomorrow.’
Tiny balls of relief scatter around my body. ‘Excellent!’ I shake his hand. ‘I’m looking forward to working with you. Next year I’m planning to add payment functionality. A revenue model should mean —’
He swats the air if he doesn’t want to know. ‘You’ve sold me on Posse. I’m backing you to pull it off.’ He holds his finger up for the waiter again. ‘My friend here only eats seafood,’ he says. Then to me: ‘Do you like caviar?’
I try to picture caviar in my head. ‘I don’t think I’ve had it before.’
He folds the menu. ‘We’ll get two of the caviar with the toast, the crème fraîche, a dozen shucked oysters, and the grilled lobster for mains.’
He rests his arms on his stomach like a pillow, rocking back on his chair. ‘Now, I want to learn more about Rebekah. Tell me, where did you grow up?’
We chat about New Zealand and my early attempts to start businesses. ‘When I was nine years old, I used to look for lost golf balls and sell them back to the shop.’ I ask about his business in New York: ‘What got you interested in startups?’
‘My father was in real estate. He made a lot of money doing apartment buildings in the eighties. My brother’s still in the game. I just get more excited investing in people and ideas, you know?’
The caviar arrives and Mike takes my plate as well as his. ‘Let me put this together for you.’ He doles scoops of cream and black egg jam onto tiny pieces of toast. ‘You’re going to love it.’
I watch Mike as a guide for how to eat; he devours each piece of toast in single bites. I hold the toast in my mouth, consciously taking in the taste which is fresh and strangely delicious. He coats the oysters in mignonette sauce and hands them to me one by one.
Our conversation is friendly and relaxed. I like Mike. This whole expensive dinner charade is bizarre, but he obviously thinks he’s being impressive, treating me to fancy wine and food. I giggle inside at the strangeness of men. A nice salad and a juice would have been fine.
Next, two giant halves of lobster arrive on a plate, coated in garlic butter.
‘Do you know how to eat this?’ he asks.
I shake my head.
He takes the white napkin from his knee and stuffs it into the top of his shirt like a bib. ‘I’ll break it up for us.’ He grasps a lobster half. ‘There’s a psychology to this. It’s a primal instinct sort of thing. You just rip into it.’
He twists the body slowly until it cracks; garlic butter and lobster juice coat the wiry grey hairs on his fingers in yellow. I gag a little and swallow my breath. ‘There’s meat in every nook and cranny of this lady,’ he says, stacking chunks onto my plate.
As we eat, I notice sweat dripping down the sides of Mike’s head. He uses his napkin to wipe his brow, the sweat oozing though his hair to create a gel-like effect. He really shouldn’t be eating all this rich food, drinking so much wine. I picture him collapsing forward on the table, me calling an ambulance.
We continue to chat. Mike tells me about his grown-up daughter who’s a fashion designer in London and his son who’s studying law at Yale. ‘I wanted him to go to Harvard, but his mother lives out there in Connecticut.’ He presses his lips together. ‘And what about you? Any children?’
I laugh. ‘No.’
‘Husband? Boyfriend?’
I glance over to the kitchen. ‘Ha, no, not at the moment. I date sometimes, but I don’t have a lot of time.’
He wipes his hands and face again, soaking his white napkin yellow. ‘Starting a business is a big commitment. I know what it’s like.’
It’s getting late and I can feel my stomach struggling to process all the rich food. I’ve carefully sipped wine to give the impression that I’ve drunken more than I have. Mike polishes off the bottle and I’ve still got a full glass. Mike waves to the waiter. Phew, he’s going to ask for the bill. I’ve got to be up for yoga at 6.
‘Can we see the dessert menu?’
He orders a chocolate mousse cake to share. The plate arrives and he shifts to my side of the bench. He shovels a spoonful into his mouth and turns to catch my eyes straight on.
‘Now.’ He shuffles his hips on the seat. ‘Can I address the elephant in the room here?’
I notice I’ve subconsciously crossed my arms. Have I said something wrong? ‘Okay. I’m not aware of anything.’
‘Oh, come on,’ he says, mouth open so I can see the brown goo of the mousse strung together with spit between his teeth. ‘Let’s be honest. The elephant in the room is that you and me want to fuck each other.’
There’s silence. My entire body turns to ice. I can’t speak. Mike takes another spoonful of mousse and looks up, licking the side of his lip. ‘We both know it. I’m just putting it out there.’
I scramble for a response. Don’t be rude, don’t offend this guy. The company needs his investment. But inside I’m screaming. This is disgusting! I’m angry with the world for putting me in this position, and I’m angry with myself for what I know will be a meek and polite response. I imagine my feminist superheroes swooping in, ready to swing. I should tell him this is unacceptable, rude, verging on harassment.
I clasp my hands together and force a smile. ‘I’m really sorry if I’ve given you the wrong impression.’
‘Come on.’ He scowls, dropping a soft fist on the table. ‘You’ve been flirting with me all night.’
Stay poised. Don’t flinch. I play back the dinner in my head. The conversation had been nice, we’d shared our backgrounds, I’d asked questions.‘I was just —’ Don’t be condescending. ‘I think that’s just my personality. I wanted to get to know you, since you’re investing in the business.’
He shovels in more mousse, not caring that he’s eating all of it. ‘We should go right now. Back to my hotel and fuck all night. It’ll be amazing. We can order room service.’ His eyes gleam with the thought of it. I’m imagining too, those lobster hands unbuttoning my shirt, sliding under my bra. Him perched on the side of a hotel bed, phone in hand as he orders more food, eats more food. The oysters, the fish eggs, the $890 wine, all back in my mouth. I hold back a retch.
‘You know, I’m staying at the Wentworth Hotel,’ he says, motioning towards the street. ‘It’s right around the corner. We’ll be there in five minutes, no problem.’
This guy doesn’t get it. He thinks proximity is a selling point. He thinks I’m going to say ‘Oh, if you’re just around the corner then that’ll be fine.’
I tell myself it’s time to shut this down. I look directly into his eyes. ‘I’m sorry, this isn’t going to happen. I’m not a one-night-stand kind of person.’
He signs for me to stop. ‘Look, it’s your loss. It would’ve been fun. Forget it.’ He sniffs, making a loud sucking sound like he’s proud to be vulgar. Like he’s reclaiming his dominance. Is he still going to invest? Should I ask? He holds his credit card in the air and signs the bill for $1800.
The next morning, I delete Mike’s contact from my phone. I won’t do ‘anything’to raise the money. I step into Westpac on George Street and fill out a withdrawal slip: $160,000, almost all the money I have, save for the $11,000 I’ve put aside for egg freezing. It’s enough to keep my team employed for another two months. Just till I can close the round. I imagine Sarah shaking her head. ‘Don’t put all your eggs in one basket.’ But what choice to I have?