People of Landscape — Alex Macdonald
How long have you been an investor for?
9 years as a serial founder, 8 years as an angel investor.
What’s your backstory on how you came to be an investor?
I started my first company, Velocity Black, a digital concierge product in 2014. We raised more than $30m in venture capital and scaled the business to serve customers in more than 100 countries around the world.
I stepped up to be non-executive chairman at the start of this year in order to start my second company, sequel, which is still in stealth.
I have also been angel investing for about 8 years at pre-seed and seed, trying to help other founders on their journeys, and also learn some valuable lessons for my own.
What has been your highlight as a founder and as an investor?
Highlight as a founder: getting my first company to a position where it was generating positive cash flow.
Having experienced both hyper-growth mode where you’re burning millions of dollars a month and getting to a sustainable position where you’re generating cash, I can assure you there’s nothing more satisfying than holding your destiny in your own hands and not being reliant on external capital.
Highlight as an investor: being on the journey with Jack and Novo at Syft, where I was first cheque in through to the exit to Indeed.
What about a lowlight?
The realisation after raising a large round of capital at my first company that our product had terrible unit economics and would never scale. Everyone in the team, investors and the media cheering you on celebrating the big round… while my Co-Founder and I knew our product was not sustainable.
The story had a happy ending though as we spent one of the most intense periods of my life pivoting the whole company to a new product which thankfully grew very quickly.
How did you came across Landscape?
The screenshot below tells you the story… I offer free DNS monitoring to all portfolio companies ;). Props to Joe for turning a bug report into an angel cheque though, mad skills.
What is the biggest thing you need help with right now?
My new company sequel stands at the intersection of professional sport and venture capital. We’re looking to partner with top quartile performing funds, so if any VCs in the Landscape community would like to chat, please get in touch. We’re also always looking to expand our network of professional athletes, so any introductions on this front would be welcome!
I’m also hiring full-stack engineers and a designer having recently completed a funding round. If you’re a top percentile performer and like a winning culture, reach out to me, (no recruiters please).
Biggest mistake you’ve made so far and what did you learn from it?
I initially underestimated the importance of being deliberate about defining company culture.
It’s critical you define your culture — in terms of behaviours and values (not ping pong tables and beers) early. Write it down. Embed it into your hiring process with targeted questions. Structure your performance reviews around it.
A good culture should be controversial, it should be something that is right for your company but wouldn’t for another. It’s not fluff like ‘integrity’ or ‘honesty’ — these are hygiene factors every company looks for.
A classic example of a clear cultural value was Facebook’s old ‘move fast and break things’ — as a potential hire or new team member you know how to behave and what to optimise for.
What’s your piece of advice to other founders?
Get a leadership coach.
Most frustrating thing you find about the startup fundraising ecosystem at the moment?
The venture model isn’t right for the majority of companies. It requires going after hyper-growth. This will kill most companies (who might otherwise do very well if they grew more sustainably).
Think carefully whether the venture funding route is right for you, there are so many other options out there. Some of the happiest and impactful entrepreneurs I know never raised a dime of venture capital.
What you would like to see change in the startup fundraising ecosystem within the next 5 years?
Increased liquidity for founders and employees earlier in the journey.
This better aligns incentives with investors and I think will lead to more entrepreneurs, particularly in Europe, building big, multi-decade companies like our friends in the US rather than selling early.
- x x -
Alex is a serial founder and an angel investor. You can connect with him on LinkedIn here and follow his Twitter here. He’s happy to be contacted via both social media sites or you can email him at alex@joinsequel.co. Just drop him a DM 💬. Check out also his Founders & Investors newsletter at alexfmac.substack.com. We also recommend giving him a follow on Twitter, he’s always sharing great advice to both founders and investors 🙌.
Originally published at https://www.landscape.vc on August 25, 2022.
