‘Get comfortable with being uncomfortable’: Founders Thoughts, Tom Shrive

Askporter is a global AI management platform that manages people, places and real assets. Founded in 2016, they have quickly developed into one of the most exciting PropTech companies in the UK. Henna, Head of Beaumont Bailey’s Advisory Network, sat down with Founder & CEO Tom Shrive to discuss askporter’s growth so far, the challenges they’ve faced to date, and how the team is preparing for the next exciting phase of its journey.

Tom Shrive – Askporter Founder & CEO

When you first started this journey of creating askporter, what were the initial challenges you faced?   

People usually find it challenging to run a start-up as they don’t have a technical founder, which is essential, in my opinion. Having a Co-Founder like Sam who understood the technical challenges made a difference.  What I find challenging is that you’re building the tracks as you ride the train – you never quite know what’s up ahead. I’d also say that hiring is a challenge start-ups face; you must invest in the right team and ensure they are the right fit for the role and understand the company’s vision.

What helped you gain traction from pre-seed to seed, and did you rely on anyone specific to help with this?   

Gaining traction in Property is challenging in itself, but we had a great USP. We were bringing AI to Property which is quite a traditional industry. We had a good amount of organic inbound enquiries, so we knew there was interest in our offering. What helped us gain traction was ensuring we were finding and giving the right message to clients and showing where we could add value.

You’re now a team of 20+. How did you find the transition from Founder to CEO?  

As cliché as it sounds, I’ve done a lot of reading on this! A book I’d recommend for any Founder is ‘The Hard Thing About Hard Things’ by Ben Horowitz. There are some great insights for anyone making that transition. I found that you’ve got to find the balance between being a friend and a boss, and I mean that in the nicest way possible. As you grow, you’ve got to ensure you can hold your team accountable while remaining approachable and friendly. It’s super important that team morale remains high, and you keep a positive work culture as the company develops. You have to give feedback on the smaller things and ensure you’re honest; it goes a long way.

What has helped you and the team come closer to raising your Series A?  

For us, it was finalizing our pricing model as it was pretty time-consuming to get there. We had great outsourced advisors who were extremely helpful with this task. Rather than making a ‘one size fits all’ solution, we also realised that tailoring our service helped a lot. One final thing is to stay focused on the bigger vision and avoid getting side-tracked – it’s easier said than done!

Do you think the issue of burnout is addressed in the industry for founders? What do you do for support?   

As a founder in this industry, I find that the word “burnout” is thrown around a lot. Don’t get me wrong, burnout happens but I don’t think you can easily tell when it does as it’s a grey area. I have experienced burnout, but I didn’t realise it at the time. I think in the early days, while you’re doing multiple roles at once, things can get quite intense, and you might not realise it’s happened. I wouldn’t say there’s someone who can specifically help you with burnout. However, I think being able to talk to someone and vent your thoughts is important, especially to someone who isn’t invested in the business directly. Also, actually taking my lunch break (which I never really did at the start) and working remotely gave me more flexibility and time to focus on myself. You need to set aside time for yourself.

If you could go back, is there any support you wish you had or any advice you would give yourself?  

I wouldn’t necessarily change my journey as it’s helped me navigate through life, so I appreciate the good and the bad. I have an amazing Board who have continually supported the team and me, which has been a huge advantage. However, in the earlier days, it would have been great to have some technical advisors as that can change the dynamic of conversations, and you get that technical expertise at a Board level.

If there’s any advice I would give to anyone going through a similar start-up journey, it’s:

  • Pay more for key hires – really invest in your team from the start
  • Hire someone with start-up and scale-up experience – this will go a long way in helping you understand the journey ahead
  • Anyone who makes you feel like you are smaller than them ignore 100%, the best advisors talk about their failures not their successes
  • Get comfortable with being uncomfortable. The more you push your comfort boundaries, the more comfortable you become in life
  • Exercise – that really changes you for the better!


Find out more about Henna’s work with start-ups here