What it’s like to date a startup founder

Firstly, a disclaimer that this article reflects views that are my own and my exposure is limited to the startup community in Sydney, Australia.

I’m not exactly sure why I wrote this piece but I guess the main reason is I wanted to share my experience and to validate (ha) whether anyone else shares the same experiences, as the partner of a startup founder.

Some back story, when we started dating she was working two part time jobs; one was retail the other was with a Japanese marketing agency. Her first exposure and interest in startups came from a short startup program focused on developing ideas in Australia for Japan focused issues. She also developed the initial version of her idea during this program. She then participated in her university’s startup program, allowed entry as an alumni. Since then, she’s found a technical co-founder, formed a business, pivoted her customer base and is developing an MVP and hopes to raise seed funding later in the year. All this has happened in less than 12 months.

During this period, I’ve watched as she went from someone struggling to find a 9–5 full time job as a recent graduate (another topic of its own) to someone that is in the hot seat of an early stage tech startup. As a caring partner, I want a good and comfortable life for us and witnessing the struggles and insecurity of startups is not easy.

Before you comment, I’m not new to the concept of owning a business as I myself am a co-founder and director of a small digital agency in Sydney. We’ve been open for the past 12 years. My own experience in managing a business started before graduation when even Coles wouldn’t hire me due to having too many class hours; and I wasn’t ‘experienced’ enough like other graduates. Our opportunity to form the company came when myself and my ex-founder were approached for an animation job through our university lecturer (whom may I add we first learnt the concept of outsourcing, taking a 50% cut from a bare minimum output) which eventually led to an ABN, business cards, another co-founder and referral to our second client. 12 years later, we’ve experienced the highs and lows including a GFC ripple that left us crippled and in debt but forced us to evolve and adapt our business plan to get ourselves out of it.

In this opinion piece, there are a few issues that I’ve seen, heard and experienced within the startup community that worry me regarding the professional life of my partner.

1) Subconscious discrimination

Three main factors already stack up against my partner as a startup founder:

a) She’s female

b) She’s young

c) She’s a tech founder (with no tech background)

Whilst there has been massive improvements in the way professional industries treat women in the past two decades or so, the daily challenges are still there. There’s certainly still subconscious discrimination within all industries that females are now capable of mid manager roles however when it comes to top leadership roles, they are seen as too soft. I myself am guilty of such subconscious stereotypes when I play the role of advisor to her startup; I personally appreciate her openness to challenging the status quo yet I have asked her to be ‘nicer’ in meetings and phone calls as men find this intimidating.

Youth seems to be a discrimination that isn’t related to gender and it seems her viewpoints and opinions are dismissed to a certain degree because of her age. I can certainly relate to this experience as people I’ve interviewed for roles have asked to see my manager as they thought I was too young to handle the job interview (suffice to say they were surprised of my role and age and needless to say, they did not get the job). I have also been in meetings with her, where her points are dismissed but when I repeat the same points immediately after her, the other party seems more willing to accept and act on it.

You also do not see many female tech founders. Females are stereotyped in all industries to certain roles and/or industries. Account managers, finance, hospitality, retail etc. There was a recent all female validation program that she attended and she said none of the ideas were tech based. It feels like the founders are either lacking confidence to tackle tech issues or we’ve created a glass maze that gives females the perception they can reach their target but the paths certainly won’t lead to it.

2) Unqualified guest panelists and speakers

I once attended a startup event where they had five guest panelists from various startups to share their experiences as founders. You get your scripted comments and replies to standard questions like ‘what inspired you to start up your business?’ however my full attention is given when the question of ‘what has been your most difficult experience’. One founder said, I shit you not, “the most difficult experience was when a staff member left for another job, it was very difficult for me”. If this is the kind of advice that is given, my advice is to stop letting these people give advice. As guest panelists and founders, you’re there to give insights as leaders and your generic over the counter advice is not something worth sharing or listening to. Fellow startup founders are looking at these panelists for real life scenarios and issues to relate to, so they don’t feel like they’re the only ones facing the same issue.

3) Back patting

I’ve now watched several young individuals sold on the startup life viewed through rose coloured glasses and have now considered leaving due to the harsh reality they discovered. There is an incestuous culture of back patting and positivity within startup communities, where everything is okay and positive vibes will solve all problems. No, they won’t.

The empowerment of individuals to own and manage their own business is fantastic and is creating individualism in a world that will soon be engulfed by mega corporations. However happy-hippy-positive attitudes towards every problem and question is not going to help solve anything. The first step towards solving a problem is acknowledging the problem. Being publicly open regarding the challenges you are facing not only helps you solve them, it also prevents others from encountering them.

Sometimes you need a harsh reality check where issues and topics that you don’t want to talk about need to be talked about. Your family and friends are there for you to give you that encouraging back pat, but you and your colleagues need to look at issues in the eye and address it directly. My own advice to my partner and other startup members has sometimes been blunt and direct however I know in the long term, my advice is going to help more than a back pat.

4) Sexual Harassment

So this quite recent event is just one of many harassments I have witnessed my partner go through in her short journey. Some guy messaged her and started a conversation about wanting an introduction to a head of a VC firm, someone whom she doesn’t actually know. Being the helpful person as she is, she answered his various questions about Sydney startup life and tried to direct him to the right avenues, until he asked if the person in her Facebook profile picture was her boyfriend, and whether our relationship was ‘serious’.

She stopped replying to him at that point, and blocked him from sending her messages. Time passed, and we both thought that particular person had moved on but just a few days ago he started texting her. Yes, her phone number is publicly available on her website to contact her. No, having a public phone number does not invite sexual harassment.

I could write a whole piece at the sheer anger and disappointment I felt when she told me what happened, as this was supposed to be slated as a progressive community that was different from other communities. I also attended a networking event only to leave very early when I realised it was a giant singles event. How can more women become leaders in any field when they constantly face sexual harassment everywhere they go? Even Linkedin is now being used as a dating site.

5) Different jargon, same problems.

Pivot. Low hanging fruit. These are some of the terms that are often used within the startup community so members can differentiate themselves from other industries. Except, dare I say, half don’t understand it, a quarter use it incorrectly, most overuse it and that leaves the rest as the ones that use it in the correct meaning and context. A good idea does not need jargon to make it solid. What irritates me the most is that a pitch is often judged on the use of jargon, and to see young startup founders fumbling their way through these buzz words is embarrassing. This type of behaviour is not going to differentiate startups from other industries; it merely reinstates that startups are no different from other industries in that it shares the same flaws, the same bad practices, the same human error. Startups have a fantastic opportunity to write the wrongs of other industries through a progressive approach, and the progressive thing to do is to get rid of jargon and just say it how it is.

6) Our relationship behind closed doors

I end this discussion on a personal note about my own experience as a partner to a startup founder. Watching her grow as a person in the past year and a half has been a privilege, I want nothing but for her to succeed as a business founder. However watching her quit her two stable jobs to pursue her own thing has made me worry about our financial future. Will we be able to go on holidays? Should we purchase that gift for the baby shower? Should I buy the $3 bread instead of $4 bread? I’ve have gone through the personal sacrifices of living bare minimum in my own path as a company founder , however it is more difficult to watch someone I care about go through the same process. What I felt is probably the same thing my parents felt when I went through the same process, and I’m grateful for their support.

Often, the business partners, advisors, and professional colleagues are the first to praise founders for their success, but when things aren’t going right, they will pat you on the back and tell you ‘keep trying’. Even friends and family can sometimes be limited to what they can do when a startup fails. However, it is the partners that witness and experience the full burden of failures behind closed doors; financially, emotionally and physically. I’ll be the first to congratulate my partner on her success, but I’ll also be the first to give her a hug when it doesn’t go well. I carry this heavy burden because I want her to succeed and break through all the discrimination that our social construct have placed upon females. When she succeeds, I hope it inspires future female founders to aim higher, to reach further and not be held back because of her gender.

So to all startup founders, go and give your partner a hug. If you don’t have one, say thank you to the friends and family that have supported you. Because at the end of the day, rain, hail or shine, they’ll be the ones that will stand by you, even if you’re bankrupt.

This story is published in The Startup, Medium’s publication followed by over +256,410 people.

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