I recently went one on one with Jeff Taylor, founder and CEO of Courier. Courier’s newsletters reach more than 1 million people each week; the magazine can now be found in over 25 countries around the world; and in 2020, the business was acquired by MailChimp.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your growth? 

Jeff: I started Courier as a reaction to everything my professional career had been up until that point. I was working in what I’d always thought would be my dream job, flying around the world launching brands and investing in emerging consumer technology businesses on behalf of my (then) employer – but all the while I was secretly frustrated and exhausted. As I chatted with friends, I realized there was a commonality. So many of us were looking to ditch our careers and do something new, but there was very little in the way of media or community for people who were looking to do what I was doing. The predominant media narrative at the time was centered around technology and the Bay Area and the overarching theme was the desire to get rich, cloaked in a thin veneer of ‘wanting to change the world.’ My experience at the time in dealing with many founders who would go on to become household names had convinced me that the desire to get rich was by far their defining ambition even then. Yet when I spoke to so many of my friends I’d find that, like me, building a solid financial future was of course an important part of our plans, but our motivations were far broader and more around living balanced, higher quality lifestyles and fulfilling more ‘inner directed’ needs. 

I’m Australian but have lived in London for many years. Every year I would go home for Christmas and spend a month in the Australian summer at our beach house outside of Melbourne. It was around New Year’s close to a decade ago, sitting surrounded by grape vines and fruit trees in our backyard and fresh back from the beach, that it hit me that I just needed to get on and start something if I wanted to change the balance of my life. The decision was made and I quit my job a few weeks later with only the barest idea of what I was going to do. The basic thought was there, but in hindsight I can’t believe I jumped with so little in the way of plans. But I had the security of a good reputation and quickly picked up consultancy and creative jobs to maintain my income while I set about firming up my thinking around what would become, around twelve months later, the very first incarnation of Courier. 

I rooted Courier in media as I felt it was a great way to bring a community together and build a relationship based on shared values, taste and ambitions. The decision to base our media ambitions initially in print seemed counterintuitive to many people around me, but to me it seemed obvious. While larger print magazines were struggling, at the independent end there was a flourishing market for high-quality, audience (as opposed to advertiser) centric publications and, even more importantly, there was a clear way to monetise the product. In retrospect I’m so glad I took this path in spite of the advice of others. When everyone was going digital and trying to monetise somewhat nebulous online audiences and third party online ad brokers, we were able, with a physical product, to create a real environment of desire for brands and charge a significant premium for space. And of course we also got to charge (in later years) a cover price for our readership, something that still eludes most digital media to this day.

Our first edition was 32 pages with a print run of a little over 1000 that we distributed by hand to artisan coffee shops, tiny boutiques and places like Soho House in London’s then buzzy Shoreditch area. They flew off the shelves and were gone before we knew it and we knew within a week that we had something others could respond to. This week we’re about to go to print with Issue 42, which clocks in at over 160 pages and that will sit on shelves across 30 countries in outlets that range from tiny boutique hotels and small coffee shops to national chains like Whole Foods, Barnes & Noble and WHSmith. 

In time we added other media channels that we felt would help fuel our audience’s appetite. Our weekly emails now reach over 1 million people around the world, we’ve recently launched our first hardcover coffee table book, we publish guides, myriad online resources and stories, post frequently to Instagram and Twitter and, as Covid restrictions ease, will return to running events in our home town of London and increasingly in cities across North America too. It’s been quite a ride! 

In late 2019 we were getting ready to close our first serious round of investment. Mailchimp had been a brand partner of ours for a few years and had always been super supportive of the work we were doing. Before the round closed they expressed an interest in acquiring us. I was initially 

hesitant given we were doing really well on our own and growing aggressively. But as we chatted more I realised it might be a great way for me to more rapidly get Courier to the size I’d dreamed of for it and also for me to be able to monetise my position. A few months later we agreed on an arrangement and in March 2020, right before the pandemic hit, Mailchimp acquired the business. I still run Courier as I always did but having the support, expertise and reach of a business like Mailchimp behind us has been transformative. Not only did we ride out the pandemic, we were able to grow significantly by being there for our audience in a time of significant need. 

Adam: How did you come up with your business idea? What advice do you have for others on how to come up with great ideas? 

Jeff: The idea, if you could even call it that, for Courier I guess evolved over a period of time. My experience with Courier but also in talking to literally thousands of other founders over the years has convinced me that the search for this El Dorado of an ‘idea’ is, in many cases, a red herring. There are precious few really unique ideas out there and the idea that successful founders have some kind of eureka moment sitting in the bathtub is just false. The much more consistent experience I hear about, and it certainly gels with my own, is that most successful founders find an audience they know well (through research or more often proximity) and find a way to solve a significant problem for them. In many cases this isn’t really something completely new and unique. More often it is taking something that is kind of broken or poorly executed and just doing it a whole lot better. That was certainly my experience. Business media have been around for years. Chambers of commerce have connected founders for decades. But nobody was creating media or connection for a new generation who didn’t in any way identify with the old, white and very masculine tropes of ‘business’. The awful stereotypes of business media and reality TV programs like The Apprentice were at complete odds with what I and my peers were looking for.

So really for us it was less an idea that was original and more a complete reimagining of an archaic, tired sector for a new generation. 

Adam: How did you know your business idea was worth pursuing? What advice do you have on how to best test a business idea? 

Jeff: We put something out and watched. Simple as that. I think when you’re trying to find a place for your product there’s a very delicate balance you try to maintain. On the one hand to break through you need a vision that is tight and consistent and appealing. Try too hard to please the audience on all counts and you risk diluting your special something and becoming the same as everything else in the sector. On the flip side you need to watch carefully and listen to your early customers to tweak and nudge and refine your offering. It's not an easy process but my best advice comes back to the idea of audience proximity. Your job as an aspiring founder isn’t to ask your customer what they want and just deliver it. Anyone can do that. Instead you have to become a really finely attuned intuitive. You need to know not just what your audience wants now but more so what they might want should the opportunity present. What they’ll need down track. Where you can take them from where they are now. These are the questions I think it’s worth obsessing over and certainly the way I built Courier in the early days. 

Adam: What are the key steps you have taken to grow your business? What advice do you have for others on how to take their businesses to the next level? 

Jeff: I’ve tried to always grow the business with what I call organic pressure. I think to a large extent you can’t force growth. Products need to find their markets and sometimes that takes time. For our initial offering, a print magazine that comes out every two months, you need time for customers to discover you in that airport bookstore, pick you up and flick through, and perhaps put you back on the shelf only to revisit you the next time they travel and decide to give you a try. It’s very easy in the early days to assume that the solution to growing is just throwing money at promotion. It’s not to say that promotional spend can’t work, but if you build your growth purely on high marketing spend, as many DTC players are currently discovering, you create very weak foundations for the future. Marketing spend is like a drug. It gives instant gratification and the sales numbers do light up, but very quickly you’re seeing your numbers fall and the only way to reach the previous high is to take another hit of spend. The way Google and Facebook work, over time your CPA creeps higher and higher and before you know it your margin isn’t sufficient to feed the beast. 

That said, you can’t just sit back and hope the gods will step in and make you a success. What we always tried to determine was where the absolutely most efficient use of time and (occasionally) spend could be directed. If you’re not in a spend-first mode, you tend to be far more creative about how you grow your business. You look for partnerships, collaborations, deeper relationships with your third party channel, you invest over and over in improving your online presence and experience, etc. This relentless pressure directed where you can already see traction worked well for us. 

Adam: What are your best sales and marketing tips?

Jeff: Focus on relationships. Get close to your fans. To your stockists. To potential collaborators. Feed indirect word of mouth rather than launch straight into spending directly to promote yourself. You won’t gain as many overall customers doing this, and it takes a lot longer but you’ll amass over time an incredibly loyal group who will both do a lot of your promotion for you and also spend a lot more with you over time. Like anything good, it takes time and patience and hard work. There are few quick and easy wins out there. 

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level? 

Jeff: It’s such a tricky question. It’s like asking someone to judge if they are a good singer, or look good in a pair of stretch jeans! You never really know how good a leader you are I guess. I’m not naturally a really good listener to be honest, but I found when I started working on my listening and asking questions more than telling people what to think that great things started to happen. I also try to take time to think about how I can adapt my style to different members of my team. My job as leader is to inspire, to support, to teach and to encourage. But different personalities respond so differently. In recent years I’ve focused more on thinking about how I can adapt my style, without of course changing fundamentally who I am, to better suit different members of the team. 

I also think communication, while cliched, is paramount. I’m a good communicator but as the business has grown, I’m realising I’ve not necessarily created as many opportunities for our wider team to hear from me as there were in the past when we were much smaller. I’m working on that at the moment to ensure everyone feels as connected as possible which is doubly important with everyone still working from home. 

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders? 

Jeff: To entrepreneurs I think leadership is all about building stamina in yourself and your team. Building a business isn’t, for most people, an overnight success. Learn to harness your energy and expend just enough that you can recover to do it all again tomorrow. The culture of a few years ago where founders celebrated all night sessions and work hard/party hard mentalities simply don’t last the distance. You exhaust your staff but more importantly, you exhaust yourself in the long run. 

To executives, it's a cliche, but I think leadership is about getting out of the reality distortion field that large businesses can create to comfort themselves and experience the reality of your brand and your business ‘in the wild’. I’ve worked alongside countless CEOs who have been convinced by their army of ego-stroking management consultants, advertising agencies and law firms that their business is relevant and in great shape for the future when actually just a simple conversation with ‘regular people’ quickly brings up ample evidence that the business is simply trading off its legacy as it slowly calcifies into irrelevance. A leader’s job is to rise above the noise of the day to day and recognise when the ship is off course.

For civic leaders I think a large part of leadership is rising above the temptation for short-term gain and looking at how we can lead our communities to much stronger long term outcomes. The devastation of locally-owned small businesses in so many neighborhoods is a classic example of this. Community leaders became enamored over the past few decades with trying to echo many of the cues of larger government, choosing to favor big chains, large corporations and the like rather than pay real attention to what I believe is the fabric of any community: its small businesses. Smaller businesses play an incredible role in our community. They employ local people, they give opportunity to those for whom college and a profession aren’t possible, they keep an eye on our streets, they connect locals with each other, etc. I strongly believe so much of the decline in so many of our communities is completely correlated to the evaporation of support and opportunity for small business. 

Adam: What is the single best piece of advice you have ever received? 

Jeff: In one of my first real challenges with Courier, someone who would go on to become a dear friend and an incredible mentor gave me the most useful advice I’ve ever received. We hadn’t taken investment and for the first year I often fell prey to the same conclusion so many others do around the need to bring in external money to fund the business. Nikki had a different take. Her argument was that shares in my future were worth so much more than any investor would pay for them right now – and that to give them away for a pittance would be an incredible own goal. Instead she gave me a phrase I’ve used time and again and shared with so many others: ‘See how far you can get on without taking investment’. The great thing about that was not only was she right in her assumption that I was just being a bit lazy in thinking other peoples’ money would be a panacea for all my challenges, but also that that one piece of advice led us to come up with so many far more creative and ultimately far better solutions to our challenges. Over time I’ve learned to see that problems are really just like weights in the gym. They’re there not to stop you forever but to condition you to be able to deal with them. It’s an incredibly useful paradigm that has stood me in really good stead and that has made the inevitable endless stream of challenges so much easier to navigate.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

Follow Adam on Instagram and Twitter at @adammendler and listen and subscribe to Thirty Minute Mentors on your favorite podcasting app.