For the past three-or-so years, I have been writing the blog 17000credits.com. I started it in large part due to a friend in college (Josh Kramer) who was a die-hard sports fan. Actually, fan doesn’t do him justice - he was a complete sports nut. At some point in middle school, he went as an ESPN sportscaster for Halloween. His dream was very clear early on - he wanted to be in the sports business. So, when he was traversing his way through the Lindner Honors-PLUS program at the University of Cincinnati, he had a buddy tell him to start a blog about sports - that way, nobody could deny his passion and drive. Thus, The Sports Kraze was born. He wrote ALL THE TIME. And everywhere he went, he handed out TSK business cards to spread the word. When I first heard about what he was doing, I thought it was kind of funny - “man this guy really likes sports, how weird?”. But after about the third time hearing about how he wrote a guest blog for Paul Daugherty or the YES network, I realized my skepticism was kinda dumb.
Josh wasn’t selling snake oil. If you read his blog, you could tell he was doing his research and paying attention. His blog was well written and very well-informed. It was also his unique voice. He was sharing it with people because he wanted feedback and because he just wanted to talk sports with anybody who would listen. Sure he wanted pageviews and subscribers, but that was secondary to his primary purpose. After a while, everybody knew Josh as “The Sports Kraze” because of his blog. He had that brand locked up and - most importantly - that’s who he actually was. And after a couple of interesting sports-related internships, he landed at ESPN. Right now, he’s a segment producer at The Worldwide Leader - that Halloween dream costume came true.
So for a while I held that thought in my head - “Josh started a blog and it helped his career, wish I could do something like that”. But I never did that something. In college I was obsessed with getting a job in corporate / investment banking, but I never started a finance blog. That’s probably because I was only chasing “ibanking” because that seemed like the only option as a finance major coming out of school - not because I had any real interest in the space. After some internships and a couple of years in banking, I realized that I wasn’t sure why I wanted to get into that profession in the first place.
So I started interviewing with a bunch of people in a bunch of different professions that seemed adjacent to what I wanted to do - consulting, strategy, different variations of investment banking, corporate development, and even b-school graduates. But then I started talking to some venture capitalists (after advice from my wife). And I realized I was always far more interested in what they had to say than any body else. It wasn’t just venture capital - it was technology finance that really sparked my interest. I had grown up in love with entrepreneurship and watching people build businesses (thanks in large part to my Mom, who is an entrepreneur extraordinaire herself). It had never occurred to me that I could help other people build businesses too. And after spending several years in finance, I realized there was a lot about that which I liked as well. So venture capital made perfect sense - it was the merging of those two passions I had developed.
But how could I possible make the pivot from banking to VC? Actually, how could anybody break-into-VC? I thought about my old buddy The Sports Kraze and I started a blog. First I wrote investment memos for tech startups I found interesting. Then I branched out and wrote a bunch of different stuff in and around startups. I loved the feeling of writing and I could feel myself growing from the experience. It definitely played a part in me landing my first job in VC.
But now that I have been in VC for two years, I don’t have any interest in slowing down my writing - just the opposite. I want to write more about the things in the world of technology finance that interest me. So I am launching this letter in an effort to keep myself honest. I am telling you now that I am going to post every Thursday evening, so you can have something to read Friday morning. I am going to focus mostly on entrepreneurship, technology, finance, and where those things intersect. I am also going to write a little bit about life in between those topics because why not - I trust you.
If I have added you to this list, it’s because you are someone I respect professionally in some capacity and I want to hear from you when I write. Sure it’s a run-of-the-mill newsletter, but I am writing to you and seeking to hear from you about my opinions.
Coming back to Josh, it wasn’t the first time I saw someone do something creative and interesting and dismiss them, and it certainly wasn’t the last either. One of the benefits of writing is you get to semi-crystallize some of the lessons you pick up on your journey. Ironically, one of the bigger lessons I learned about writing, I never found a way to make stick.
So, for posterity’s sake, I wrote down a couple of the lessons I learned from Josh Kramer’s sports blog back in 2011:
Don’t underestimate crazy ideas. A lot of times they seem crazy because nobody else is doing them - but that is precisely what is going to make them successful. I have realized the reason a lot of things don’t get done is not because nobody ever had the idea to do something, but because somebody had an idea and thought to themselves “that will never work”. What a total crock of shit. Mark Zuckerberg created facebook well after the advent of social media when everybody thought it was a lost sector. By the time Google rolled around, the idea of starting a search engine was a meme. Basically anything Elon Musk has ever done started with someone telling him he couldn’t do it. And, don’t forget, Josh Kramer now works at ESPN.
Don’t be afraid of personal branding. The one thing that most people are pretty good at figuring out on their own is authenticity. Sure some people are naive, and some are extreme skeptics. But it doesn’t take long for most folks to spend some time with a person or an author and figure out whether or not what they are saying is authentic. If the brand you are selling is actually who you are, it’s less an exercise in personal branding and more an exercise in self-expression. So long as the brand you are trying to build actually represents your person, there’s no shame in sharing that. (Unless who you are as a person is exceptionally god-awful).
Write a blog and share your ideas. I learned this from the Kraze and I have learned it from basically every blog I have ever written. You don’t really have a strong grasp of an idea until you write it down. And even then, after it’s written, sometimes it requires having someone else read it to tell you the idea is stupid. Nothing helps you build an argument quite like arguing with someone.
Let people know what you want to do. I want to help entrepreneurs build great businesses in the Midwest. That’s my guiding north star and practically everything I believe in.
Consistency is key. The Kraze wrote a LOT. He worked out his kinks over the course of several years and learned a lot about his craft. One good blog is the result of writing several mediocre blogs.
Never doubt the Sports Kraze. Josh is somebody I really look up to. He’s had a big impact on my life, both directly and indirectly. There are few people I am cheering harder for than Josh.
Friday Links
I do a fair amount of internet article reading. It’s an outgrowth of spending a decent amount of time on Twitter. But I frequently find myself wrapping up an article and thinking, “Wow, I need to share this”, but Twitter just never does the trick. I can’t expound on how I feel about the link enough and I never give myself enough time to think about what I just read. So instead of only doing that, I am going to post the most interesting things I have read in the past few days and share them here.
Why investors are paying 10x revenue for the best software companies
One of the best and most precise explanations for SaaS multiples I have read. Sometimes the best writing is short, sweet, and athletic. The punchline here is that while most SaaS businesses have the shiny veneer of being a risk technology business, they are actually steady-eddy cash-cows. They are reliable, high-margin businesses. An MBA student couldn’t come up with a better case study for an exemplary business. And what’s even more exciting (for me, at least), is that the creation of these kinds of businesses is not going to slow down any time soon.
Sam Altman put into words something that a lot of us already know to be true - the difference between good ideas and bad ideas is very rarely intellect, but instead relies on volume and belief. From everything I see, whenever someone has an idea, most of the world is willing to shoot it down and tell them why it doesn’t work. The thing I always try and challenge myself to do is: instead of shitting on someone’s idea, I try and find a way that it could work.
That’s all I got for you folks this week. Let me know what you think.
HELL YEAH BROTHER. I couldn't sleep last night and I woke up to find out the puppy had pooped in OUR bed but things aren't so bad because my favorite Midwest VC just committed to pumping out some WEEKLY content!! Strap me into a rocket and fire me into the sun 🚀☀️