Jake Jenner is the co-founder and CFO at Howbout, a social planning app that makes organising anything with friends easy.
1) To kick things off, could you tell us a little about your career background and current role?
My current role is Co-founder & Chief Financial Officer of Howbout, a start-up that two of my best friends from university (Neil Tanna & Duncan Cowan) and I launched in 2020.
Howbout is an app for your social life that allows groups to instantly find when they’re all free, easily organise plans and manage all their social circles. We’re a team of six, so I’m involved in a few different areas such as finance & HR, operations, analytics and user success. We recently hit 1,000,000 plans organised on the platform, so things are incredibly busy right now!
Before Howbout, I was an investment banker advising on M&A in the tech, software & data sectors, before a brief stint in private equity investing in companies in the same space. There were many things I loved about those roles, but my dream was to be on the other side of the table building a business, not just advising or investing in one.
Having worked in high-intensity, fast-paced roles since I graduated in 2015, finding work-life balance has been one of the biggest challenges of my career so far, and it’s something that I’m really focused on heading into 2022.
2) What does a day in your life look like for you? Can you take us through a recent workday?
We’re temporarily working remotely at Howbout over the Christmas period. A typical WFH day for me looks like this:
- 7-9am: wake up and hit the gym (healthy body, healthy mind!)
- 9-10am: kick-off calls with the team and any sub-teams (catching up with founders, planning marketing initiatives or discussing product development)
- 10am-1pm: deal with user feedback and review latest analytics and metrics
- 1-1:45pm: short lunch break, ideally with a quick walk round the block to clear the head
- 2-6pm: collaborative tasks with the team and prep work for advisor and investor meetings
- 6-8pm: any other founder-related tasks (normally time for me to crack out my beloved Excel spreadsheets)
I have dinner around 8pm and aim to chill out from that point onwards, if possible. 7+ hours sleep is optimal for me, so I try for that every night.
3) Does your current role allow for flexible or remote working? If so, how does that fit into your life and routine?
At Howbout, we’re currently running a hybrid model where we work 3 days in the office and 2 days working from home. We love this set-up because it allows us to set the plan for the week together on Mondays and celebrate the end of the week together as a team on Fridays.
The additional office day can be moved around and used when we need full-team collaboration. The WFH days are great for individual execution and help to balance out some of the commuting.
The biggest challenge we’ve seen with WFH is the lack of separation between work and life. This is especially true as a start-up and even more so as a co-founder – you need to be a lot more disciplined and potentially set a cut-off time to get away from work, or you can easily spend all night working without thinking about it.
As great as that can be when you’re in a critical period, it’s not a sustainable or enjoyable way to work in the long run.
Working from the office forces disconnection from work because of the change to environment and travel which I think is a really positive thing. The only difficulty can be the commute, but if you allow some WFH days, it helps to balance everything out and keep things fresh.
4) What does work-life balance mean to you and how do you work to achieve that goal?
For me work-life balance is about being ambitious, working hard and achieving your goals whilst acknowledging that there’s so much more to life than just your own work and career. For me, it’s really important to make time for people that matter to me and to be ‘present’ when spending that time together.
Achieving that balance isn’t easy, especially with smartphones buzzing constantly and remote working which can mean work happening in your home and often popping up on your phone too (shout-out to Microsoft Teams).
I’ve almost always got my phone on ‘Do Not Disturb’. This feature stops the constant vibrating and pinging of notifications until I’m ready to look at my phone and take them in. I find this incredibly helpful for managing distraction and stress during work and personal time.
5) In the past 12 months, have you started or stopped any routines or habits to change your life?
I used to be very rigid with my routine, especially in the morning to ensure I got my gym workouts done before work. This meant that if a deadline came up, I could be working late into the evening, even if I was being slower and less productive than I would’ve been in the morning.
In the past 12 months, I’ve flipped this on its head: if I’m working late but being inefficient, I’ll stop working and get up earlier the next day to finish up when I would normally be at the gym. If I have time to go to the gym the following evening, I’ll go then, or I’ll just use a rest day.
This flexibility in my own routine has really helped me manage stress and maintain some balance even when there’s lots of work at a crucial time.
6) Do you have any favourite books, podcasts or newsletters that you’d like to recommend?
A family member recently recommended the Business Wars podcast to me. It dives into battles between the big brands we know today, taking you through their history, how the market developed and how things are going today: think Tinder vs. Bumble, or UberEats vs. Deliveroo.
I find it super relaxing and inspiring to hear about the big challenges and decisions these companies made to reach the levels of success they have today!
7) Are there any products, gadgets or apps that you can’t live without?
Hands down this has to be Spotify. I love music, and I come from a generation where downloading songs was expensive and a massive pain. These days I’m constantly listening to music when I’m working, at the gym, chilling out, travelling – I’ve never got so much value out of a subscription!
Recently I’ve also become obsessed with Duolingo. Learning languages has never been my forte but I’m finding the bite-sized approach really helpful. I’m currently learning Greek (my partner is from Greece) and I’m aiming to get to a conversational level, even if it takes me a while to get there.
8) If you could read an interview about work-life balance by anyone, who would that be?
Sheryl Sandberg, COO of Meta (fka Facebook), is someone I’m getting more and more interested in learning about.
She’s been incredibly influential in getting Meta to the company it is today, and all the while she’s managed to raise a family and have an impressive life outside of direct work. There are probably a few articles on how she’s managed it – this has triggered me to go and find them, thanks!
9) Do you have any last thoughts on work, life or balance that you’d like to share with our readers?
Working hard and being ambitious can be really positive for you and the people around you, but this old mantra definitely applies: “You can have too much of a good thing”. Burn out is very real, and balance is needed so you can stay in the game long-term, reach your goals and enjoy the journey at the same time. Life is a marathon, not a sprint!
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