The 0 to 5 Million Podcast is hosted by Ollie Whitefield and Shawn Finder. As the name suggests, the show is all about having honest conversations with founders, CEOs, and revenue leaders from businesses between 0 and 5 Million in ARR (Annual Recurring Revenue).
Creating a company is an ambition many of us harbour. It can bring with it unparalleled freedom, a lasting legacy, prestige, wealth, and the ability to do good. Across social and traditional media the feats of founders big and small are lauded for their efforts on a daily basis.
Indeed, many entrepreneurs go to great lengths to showcase their backbreaking hard work and eye-popping success. An outsider would be forgiven for believing that every founder is living the dream as a result of their talent and toil.
But as with nearly every image projected online, the reality is quite different. There is another, less glamorous side to being a founder. High pressure decisions. Constant uncertainty. Fear of failure. The experience is usually a rollercoaster ride of highs and lows. And that’s what Ollie and Shawn set out to explore with each of their guests - what is life really like for founders deep in the trenches of running a startup.
We caught up with Ollie Whitfield to learn more about The 0 to 5 Million Podcast and how their team deal with some of the common challenges that arise when producing a weekly show - from repurposing content to preparing for interviews.
How would you summarise The 0 to 5 Million Podcast for those that haven’t heard it?
The 0 to 5 Million podcast is by founders, for founders, about being founders. All the ugly, and the pretty parts of growing a company. The mistakes, the wins. Founders know that growing a business isn't easy. It's not an Instagram-life, it's a grind. We get behind the scenes and hear exactly how Founders in all kinds of markets, with all kinds of business models are making it happen.
Which of your previous episodes do you feel really captures what your show is all about? And why?
My personal favorite episode was our first. Peter Caputa at DataBox. One of Hubspot's first 20 employees. He grew their partner program to 10 million then joined DataBox as CEO. What attracted me to them, and how I know them, is their marketing. They're everywhere. A content machine. Podcasts, blogs, integrations, social media. You can't NOT see them. And I like that approach. Plus, Peter's Twitter is a goldmine of SaaS business growth and scaling advice. So yeah, he's the first guest I approached and the first we published.
Which aspects of running a weekly podcast have you found most challenging? And how have you overcome those difficulties?
The challenging part for me personally has been creating and organizing the promo material we use. Our video team does the lion-share of the work on this, but they need a prompt. I am there on the recordings and provide them with the timestamps for the best clips from each episode. So that, and content repurposing. We are working on that a lot. It's a shame to record with a top tier guest for 20 minutes and then release it once, and leave it to die. We know we should be doing more of this, it's just the time and process that we haven't nailed as yet.
What advice would you give to other podcasters in relation to preparing for and recording interviews?
Over-prep can kill the episode. Get comfortable with Improv and you won't feel a need to prepare so vigorously. My prep with my co-host is a very short email with 5 points on it. Who the guest is, their company, and what it does. Then, 3 loose questions which we can go through. The rest, we work out as we are in the conversation. That's where we can go down rabbit holes and ask follow up questions to get to the real gold from our guest. Surface level questions never uncover something amazing or truly applicable.
Are there any recurring tips, insights, or themes that come up again and again with your guests in relation to building a business?
It's funny, when we ask our guests if they have any good mistakes they are willing to share with us they always say "how much time do you have" or something to that effect. Everybody has a ton of mistakes, fails, face-palm moments. And life is so saturated with idealism, perfectionism that we don't realise our mistakes are OK. And everyone is making them. The number of times that we have asked this question and received an answer that on the face of it, sounds obvious would amaze you. But you don't know what you don't know. The only way to grow is to make the mistake and grow past it. Hearing tons of Founders I respect and can learn from has taught me that.
What does the future hold for The 0 to 5 Million Podcast?
I'd like to go super, super, super up-market with some amazing guests occasionally. We will stay true to the 0 to 5 million range as per our show title. But occasionally, it would be a real treat to bring on a massive name. Or a person in a huge company who has been there since the early days. And we really enjoy recording debate episodes. No guest, just raw and uncut POV from us on a specific topic. It's good fun and drives good engagement.
If you'd like to get in touch with Ollie, you can connect with him on MatchMaker.fm