0:00Introduction

So for the sake of the audience why do not you give everybody a little intro as to who you are and what you are doing right now and then we will go back into the rest of your journey later. Sure. I am Jess Walker and I am the programs and community manager at AirTree. I run a program called Explorer and Pioneers which we can jump into. I also do a bit of investment through the Explorer program side.

2:30Early entrepreneurialism

I have probably been in the startup space for more than 10 years. I started out doing little e-commerce businesses in high school and university. Fitness bands, makeup products, things I thought people in my demographic would also like. I would pick a product, buy in bulk, rebrand the whole thing, build a WordPress website, and sell them. Not knowing what any of that actually meant. I started younger than that. I would buy bars of chocolate and sell them on the bus for a profit. Supply and demand. I had this little book of startup ideas and I would go around and just listen to all people’s problems because people love to complain. I would write it down and then conceptualise what that business would look like.

5:00The influence of her mum

My mum had her own aerobics company. She would bring me to her aerobics class as a little three-year-old and try and run the class with me running between the people. Then she had a few other small to medium-sized businesses like cleaning companies. I saw her work really hard. Nothing was very structured in terms of go-to-market strategies or product-market fit. None of that was in my mind. But I have always been interested in starting something. That is why I had that little book of ideas. I still have the book and some of them are terrible.

7:30The New Zealand Airbnb business

At 22 I started my first company. It was an end-to-end service management business for Airbnb properties in New Zealand. One of the first ones in the space. I had no idea what I was doing but I would work on the business before work between six and eight-thirty and then after work. One day I had no customers, no systems in place, nothing, and a piece of media came to me out of the blue. The radio said hey Jess I really want to do a story on you and your business. We have the Lions tour coming to New Zealand and we need accommodation. He asked if I had an ops manager or sales manager he could interview. I said yes and I called my boyfriend at the time and said I need you to be my office manager and do this interview in half an hour. He went through the questions. He came back and said no, you need to call the journalist back and do the interview yourself. So I did. From there we had four more pieces of media in 48 hours. He gave out my email address and phone number on air. My website went down. My phone did not stop. I went from zero customers to hundreds. I quit my job the next day.

14:00Growing and burning out

I ended up running it for two and a half years. We grew to 10 staff. I bootstrapped without knowing that I was bootstrapping. It was a fairly operationally heavy business. It was profitable. We grew to be one of the larger ones in the country. Then I found myself completely burnt out. No work-life balance at all. I worked till midnight most nights on weekends. But I still had this inner buzz, that feeling you get when you are building something and growing something and it is yours. I got to a point where I realised I loved startups and loved building businesses, but I did not love property tech. So I decided to either find a CEO to manage it or to sell it.

17:00Being dismissed and the boardroom walkout

I was 23 to 25 in those two and a half years. A young blonde female and a lot of the time was not taken seriously at all. I have a little notes section of all these things that have been said to me which a lot of females could probably relate to. When I went to sell it I went to a broker who said that will be 50K upfront. I thought I can probably just find them myself. I went on LinkedIn and made a list of all these companies that might want to buy my company, found the CEOs, and messaged them. You only have 300 characters. I sent it to 15 companies across New Zealand, Australia, and the UK. Five came back to me. I had one meeting that really ground my gears. It was with a big real estate company in New Zealand. I was in the boardroom with the CFO and CEO, both middle-aged men. The CFO said: I am going to be a little bit PC and asked if I was going to have kids anytime soon because they just could not have that. I opened up their brochure, which had the board of directors listed, and said: you do not really tick the diversity box do you. Then I said good day and left. I called my mum and said I think I just lost a big deal. But it was probably the right thing. I ended up selling to a company in the UK.

23:00Moving to Sydney and the failed fintech

I went travelling for a bit after the sale and then decided to move to Sydney. Auckland to Sydney felt like Sydney to San Francisco in terms of the startup ecosystem mindset. The first day I got here I went to Fishburners and became a member. Then I started building a fintech company which failed. That was a huge learning curve. My domain expertise was not fintech but I thought I could do it. That is the naive startup person at the back of your mind. I found a problem to solve instead of a product to sell. But it was an interesting time and I worked alongside a range of different startups in lots of different roles because they were so early stage you are a jack of all trades.

25:30Black Nova VC

I tried my hand at VC investment at Black Nova VC. They do primarily B2B SaaS across Australia and New Zealand. That is Matt Brown and Darcy Norton. That was an awesome experience because there were four or five of us at any one time and we were building the fund from scratch. You learn everything from investor relations to how to raise money to the mechanics of a fund, through to building community and marketing which was my primary skill set. Two years and then the AirTree role came up.

27:30Joining AirTree

Before I was at AirTree it felt like an unattainable shining light. But when you get in there they are just such regular normal lovely people. First day I was like what is it going to be like and everyone was so kind. No one was glowing. A little bit disappointing. They are such a wonderful team. The access has become a lot easier. People give out their email address all the time. I think in the last two years they have grown a lot and they just seem less unattainable. They realise they need the community. It is the opposite of ivory towers.

30:00The Explorer program

The Explorer program is a three-month program where you learn everything you need to know to be an angel investor. We cover the macro environment, Angel 101, deal sourcing, deal flow, due diligence, legal, all that. We do it for two main reasons. Altruistically, traditionally investing has not been a sport for anyone who is not a white man. How do you create more diversity in that space and bring it to people who have not had the opportunity? We also want to spread AirTree’s network as a team of 30 in Surry Hills reaching Perth, South Australia, Auckland, Wellington. When an Explorer brings us a deal and we invest in it, we also give them $10,000 to invest in that startup as well. So it is the best of both worlds.

33:30The Pioneers community

Pioneers is a very new community but AirTree is going to grow it a lot. It is for Black, female, and non-binary founders. A lot of the time there is a gap around not knowing what a VC-backable business actually is. My e-commerce business is not necessarily VC-backable and I do not want it to be, but I might make a whole lot of money myself. Understanding what it means to be VC-backable and if that is the path you want to take, then helping support them. We do workshops with incredible founders, fundraising panels, and networking events.

36:00What makes a business VC-backable

LPs invest in our VC fund and it is our responsibility to try and return their money. We are looking at companies and asking can this return the entire fund. If we do not believe a company can grow to be $100 million plus then that is one of the largest pieces of the puzzle. E-commerce can definitely be VC-backable. Who Gives A Crap is an AirTree portfolio company that is now doing enormous numbers. But a lot of service businesses are not scalable in the way VCs need. It is not about quality or profit. It is about the mathematical ceiling of the market.

40:00The investment process

It is typically about five meetings. The first meeting is normally half an hour. It is relationship building: do we get along, does it fit the mandate. Then it goes to the weekly investment committee meeting. If a partner is interested you take them on the second meeting. Then you do an IC paper, usually two to three pages: what the company is, what the industry is like, market analysis. The full team does a deep dive for about an hour. Then there is a partner presentation. We try to move quickly because we know how time-consuming fundraising is for founders.

44:00The funding market

I went to Sunrise with Steve and spoke to a lot of VCs across different stages. Before Sunrise I was told all the money being raised is going to be doubling down on existing investments. But at Sunrise multiple VCs, including a very large one, told me the next three quarters is the best time to raise money. I did not know what to think. It could be because risk appetite for large Series A checks has decreased but smaller seed checks are still flowing. The runway expectations have gone from 12 to 18 months to someone telling me 48 months the other day. The one silver lining is the market is forcing founders to build sustainable businesses instead of just scaling burn.

47:00Has the startup world been glamorised too much

People want to join a startup, become a founder, go to Antler, get equity, whatever it is. If you go back 10 or 15 years everyone wanted to work in fashion and design because it looked cool. No one realised it paid terribly and the hours were super long. It is the same now. The COVID mindset shift is real and durable: people have reevaluated what they are doing and why they are grinding for someone else. But the expectation of bajillion-dollar outcomes needs to deflate. The smaller companies, a lifestyle business where you earn enough to sell eventually, is probably more realistic and more sustainable for most people.