Serial entrepreneur Rebekah Campbell reveals what it's like talking to potential Silicon Valley VC investors

Serial entrepreneur Rebekah Campbell seemed to be living her best life.

She founded Posse.com. But the one project she hadn’t built to minimum viable product was a life partner and family. In fact, she hadn’t been on a date for 10 years.

So she decided to apply her experience in building startups to finding Mr Right. She went on a date every week for nearly 3 years. And then she wrote about it.

The result is an hilarious, insightful autobiography called 138 Dates, published by Allen & Unwin and available now through all good bookstores. It’s a fantastic romp through startup hustle and how finding the love of your life is the biggest investment round you’ll ever take on.

Yes, she really did go on 138 different dates with men in Sydney, New York and San Francisco while simultaneously launching her latest business venture.

In this exclusive extract from 138 Dates, Rebekah is in the heart of Silicon Valley, meeting venture capital investors.

Sand Hill Road, Palo Alto

The Californian sun glares bright in my white hotel room. I’m staying at the Hotel Keen, a small hotel in the centre of Palo Alto. I turn on the television and an American voice makes jokes as he delivers the weather.

I pull on a T-shirt and head outside. Palo Alto is the capital of tech. Mark Zuckerberg lives here, Steve Jobs lived here. I’d expected it to bustle with lights and activity, but at 6 a.m. there’s barely anyone about. The town is small, just a handful of streets on a perfectly straight grid. Hedges and flowerbeds are manicured and there isn’t a spot of rubbish in sight. I jog from one end of University Avenue to the other in ten minutes and wonder if I’ve accidently slipped onto the set of The Truman Show.

I’m here to raise the next round of funding for Posse. Cameron has introduced me to a swag of venture capital firms, and I’ve spent the past week setting up meetings. Our team costs $70,000 per month (engineers are expensive). If I can’t raise more funding, then we’ll run out of money in December.

At 9 a.m. I start the car and key 2800 Sand Hill Road into Google Maps. I remember what Cameron told me about driving on the other side of the road: ‘The passenger goes to the curb.’ I steady my hands on the steering wheel. The route takes me past Stanford University and up onto a rolling highway with two lanes on each side. There are hills, green trees and farmland, but I don’t see any buildings. Is this the world-famous Silicon Valley? On the right, an arrow that looks more like it leads to a winery than to an office reads: SEQUOIA. The building is made of panelled wood and set into the hill.

Sequoia is one of the world’s most successful firms, best known as early investors in Apple, Google, LinkedIn, PayPal and more. I clutch my handbag. Even if they don’t invest, I have a meeting. Just a few months ago, I was a sack of nerves at Launchpad Angels. Now here I am. I take a moment to let the sense of achievement root me to the ground and I pull open the wide glass doors.

An older woman wearing a cream silk scarf tied in a bow smiles as I approach the reception desk.

Zambesi co-founder Rebekah Campbell. Photo: Supplied

‘Rebekah Campbell, here to see Bryan Schreier.’

She checks her computer and leads me down a corridor to a meeting room. ‘Right this way.’ The room is small, with a round grey table in the middle and a window to the carpark. ‘Can I get you a water or a coffee?’

‘Water would be great, thanks.’

Moments later she emerges with a bottle in hand. ‘Bryan will be with you shortly.’

I let my eyes drift around the room. Bryan Schreier is the youngest partner at Sequoia. He just appeared on Forbes list of rising stars, thanks to his early investment in a new company called Dropbox. My heart jitters like I’m about to meet a movie star. Worse, I’ll have to perform. I hunch forward in the seat and rub my arms.

I remember that TED talk about body language again. The speaker described a study where a group were instructed to take ‘high power’ or ‘low power’ poses for two minutes before a job interview. Standing expanded, legs wide and with their hands above their heads like a victory ‘V’ increased testosterone, gave the participants a feeling of confidence and boosted their chance of getting hired.

I peer through the window to the carpark. Can anyone see me? I shift to the corner of the room behind the door and pump my fists in the air. ‘Yeah, yeah,’ I whisper, punching out my arms to the side. I’m almost dancing now. Come on testosterone, I need you now.

The door opens and I spin around. A tall man with sparkling eyes and refined stubble bounds towards me. ‘Rebekah?’

‘Hi.’ I smooth my shirt to hide the air-punching crumples.

‘I’m Bryan, great to meet you.’ He takes a seat opposite and places a pen and notepad on the table. ‘Cameron introduced us, right?’

‘Yeah, he was my first investor,’ I say with pride, feeling like a member of some elite club. Cameron let me in.

‘We love Cameron. And you’re from Australia too?’ I nod. ‘Great place, beautiful beaches. I’ve been looking for an Aussie company to back. Any excuse to get down there.’ Bryan rubs his hands together. ‘Let’s hear about Posse.’

I reach into my handbag and pull out my laptop, ready to pitch. I flip open the screen and Bryan holds up his hand. ‘Do you really need the PowerPoint?’ His tone sounds disappointed. ‘I’d like to hear the story. Why did you start this? What’s your vision?’

My heart thumps. But, but. I’ve been planning the presentation for weeks. Every slide crafted with neat drawings and graphs to show our progress. Every sentence rehearsed, perfected and signed off by Cameron. I imagine his voice at my ear: Stick to the script, Rebekah. I wish I could magically transport him into the room. I can’t do this myself.

Bryan leans forward to place his hand on my closed laptop. ‘You know the YouTube guys sat there a few years ago, right where you are. They drew us a scrappy picture on that whiteboard and we got their vision straight away.’

My mind flutters, trying to remember how my PowerPoint started. I’m blank. I shuffle in my seat then sit up straight to regain a power pose. ‘I started in the music industry, I used to manage bands.’ He nods encouragingly. ‘I learnt a lot about why people share music.’ I pause. Ten, twenty, thirty seconds pass. There’s a giant hole where my brain should be. ‘I’m sorry, I can’t do this without . . .’

‘It’s okay,’ he says. ‘Just do it however you want.’

I open my laptop, feeling like I’ve flopped at the first hurdle.

In the end we chat for around twenty minutes before he asks how much capital I’m looking for.

‘1.5 million at a 4 million pre-money valuation.’

Bryan scribbles some notes on his pad.

‘What’s your process, from here?’ I ask. ‘How do you make a decision?’

‘We have a partner’s meeting on Monday. I’ll take this to the group then and come back to you with an answer next week.’

My next meeting is at 11 a.m., at Kleiner Perkins. A receptionist offers me a bottle of water and leads me to another small room. I close the door and punch ‘V’ for ‘victory’ as I wait. It’s still the beginning of a long few days. 1 p.m. is Benchmark, 2.30 Andreesson Horowitz, 4 p.m. Accel Partners. Tuesday is another five meetings, and Wednesday another six. I pop about Sand Hill Road like a vacuum cleaner salesman from the eighties. Almost every appointment is the same: a wooden building with glass doors, a receptionist who offers bottled water and directs me to a meeting room. The venture capitalist (VC) arrives: male, mid-thirties, Ivy League haircut, pastel shirt tucked in, cotton pants and boat shoes. We shake hands, I whip out my laptop and start the presentation. He smiles with white teeth, says how much he’s always wanted to visit Australia, takes notes, makes positive noises and promises to be in touch.

On Wednesday, I arrive back at my hotel just after six and walk around the corner to Sprout Café for dinner. The salad bar is packed as a long line waits to order. I join the queue, eavesdropping on conversations around me. In front, a group of girls wear red shirts with ‘Stanford’ and big numbers printed on the front. They laugh loudly and lean into one another. I order and take a solo spot in the middle of a row of tables. A couple next to me complain about an English assignment and a man wearing headphones waves to a young boy over Skype. I’m surrounded by the clatter of plates and chatter of voices but I feel like I’m caged on the outside, scratching away at the bars. I sit eating salad from a box in the bright hub of big tech, feeling terribly alone.

I rack through my memory of the past three days. I’ve presented sixteen times, met sixteen different investors. I performed well each time and they all promised they’d come back to me. But I’ve developed a radar for men who say they’ll follow-up when they actually won’t. I wish there was a woman in one of these meetings. I wonder what would be different?

It occurs to me that raising capital is very similar to dating. There’s a face-to-face meeting, a game of question and answer, and then a request. Will you give me a million dollars? Will you go out with me again? This year I’ve met a lot of men, made a lot of first impressions, but something isn’t working. None of these guys I’ve met in Silicon Valley are going to invest. And I’m still no closer to finding the one.

What am I doing wrong? I tip my head back against the seat. Is it me? Is it Posse? I throw my salad box in the rubbish and walk back outside into the warm Palo Alto evening air. The perfectly spaced trees on University Avenue are lit up like Christmas.

I don’t know what’s wrong. I kick a stone onto the road and imagine a Truman Show production assistant crouching in the background, ready to pounce and sweep it up as soon as I pass. All I can do is keep trying. Keep pitching to investors, keep lining up dates, keep looking for ways to improve.

My last meeting for the week is with a VC called Bill Tai at Charles River Ventures, who was introduced to me by my friend Lars Rasmussen.

I’d met Lars at a conference last year. Back then I was struggling to work with the website developers that I’d hired on Upwork. Someone pointed out Lars in a crowd. ‘You need to meet that guy.’ His thick blond hair and strong Scandinavian features saw him stand a foot taller than anyone else in the room.

I bowled up and introduced myself, gave a thirty-second Posse pitch and asked for advice. We spoke for a while and agreed to meet for coffee. Lars had a broad smile and his eyes beamed with so much energy they could have been lasers. I immediately knew we’d become friends. ‘Where do you work, anyway?’ I’d asked.

‘At Google,’ he said. ‘I invented Google Maps with my brother. We started it together.’

‘Oh.’

When I mentioned I was travelling to San Francisco, he immediately said, ‘You must meet my friend Bill.’

I pull open the heavy glass door and steady myself for another generic conversation. I step into the foyer and there’s no one about. Strange. I poke my nose around the corridor. ‘Hello,’ I call. No answer.

Across the room a man in running shorts and a blue T-shirt bursts through the door. ‘Rebekah?’

‘Yes.’

‘I’m Bill. Come through, I ordered lunch.’

Bill has bright brown eyes and the stature of someone who does a lot more push-ups than I do. We sit facing each other in a boardroom with two pizza boxes between us. Behind Bill is a wall stacked with plaques celebrating the multimillion- and billion-dollar exits of the firm’s portfolio companies.

‘Do you kitesurf, Rebekah?’

‘What?’

He pulls out his phone and files through photographs of himself flying high over blue water, attached to ropes and a board. I’m not sure where this conversation is going. I pull out my laptop. ‘Do you want me to run through my deck?’

He opens a pizza box and signals for me to eat. ‘We can talk about Posse later.’

I load a slice onto a plate and take a bite. ‘I windsurfed, growing up in New Zealand. I wasn’t that great or anything, but I loved it.’

Bill claps his hands together; his face is alight with glee. ‘We must get you kitesurfing this weekend. I’ll convert you.’ He starts texting and looks back to me. ‘Are you in town tomorrow?’

‘Yes, but I’ve got to be at the airport by six.’

A few seconds later his phone vibrates. ‘My friend will give you a lesson at 11. You’ll need a wetsuit.’ Bill turns to look for something and gets up. ‘Hang on, I’ll get a pen so I can draw you a map.’

Excuse me. I just sat down here to pitch my business. This whole scenario is bizarre. I don’t want to try kitesurfing. I hadn’t really liked windsurfing. All that sand, wind and seawater drying out my skin. I sit on my hands. Just go with it.

‘I run a surf camp conference thing called Mai Tai in Maui. It’s for entrepreneurs and kitesurfers. There’s some investors there too. You should come.’

‘Okay,’ I hear myself say, as if I hadn’t deliberately formed the word in my mouth.

‘Mel and Cliff will be there. You must know them.’

I nod.

‘Great!’ He claps again. ‘It starts on Monday, so you’ll need to move your flight. See if you can stay with Mel and Cliff.’

Monday? Is he crazy? I can’t get to Maui for Monday. I have investor presentations in Sydney and a board meeting.

‘Okay,’ I hear myself say again. I’m smiling too, and my chest fills with nervous excitement. Come on Rebekah, loosen up. Take a leap, a wild leap without a map. ‘I can’t wait.’

We finish our pizza and talk about New Zealand and sport and the companies he’s invested in. He flicks through gadgets on his phone like a master pianist, and my mind spins with all the tech I don’t understand. ‘I’ll follow you on Twitter,’ he says. Note to self: start Twitter account immediately.

Bill looks at his watch. ‘It’s one o’clock, I have to run.’

‘But I haven’t even . . .’ My laptop is still shut on the table.

‘You can tell me about Posse later,’ he says. ‘On the beach.’