Hi, this is Matt with a free issue of the Four Insights Newsletter. In every issue, I cover unique challenges and provide relevant insights through the lens of a venture-backed startup CEO and operator, targeting other founders, big tech and startup employees, and investors. If you'd like to receive emails like this in your inbox, you can subscribe here.
If you are new here, my topics are personal, and my goal is to highlight four valuable insights on founder/entrepreneur performance, strategy, sales, and fundraising tactics. My focus is to provide you with practical advice and inspiration from various fields, beyond the realm of pure venture capital startup jargon. Let's dive in.
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The Four Insights This Week
Creative Brilliance
Magnetic Framing
Financial Mastery
Perfect Timing
Embracing Creativity and Fear
The entrepreneur as an artist: I am becoming more and more intrigued by the concept of seeing entrepreneurs as artists. Being a fan of hip-hop music and mainstream culture, I have always been curious about the behind-the-scenes mechanics of artist marketing. There are numerous parallels between pursuing a major record deal and securing substantial venture funding.
That is why Rick Rubin's book has proven to be a valuable resource for me to delve into these ideas and apply them to my work. Rick Rubin once said:
"The artists who define each generation are generally the ones who live outside of these boundaries. Not the artists who embody the beliefs and conventions of their time, but the ones who transcend them. Art is confrontation. It widens the audience’s reality, allowing them to glimpse life through a different window. One with the potential for a glorious new view." - Rick Rubin, The Creative Act: A Way of Being
One of the more foundational founders that comes to mind as a trendsetter is Travis Kalanick. His entrepreneurial artistry peaked in the 2010s when he combined engineering, business, and community to create a groundbreaking startup called Uber. His impact was so significant that it sparked a wave of "X for Uber" startups, drawing inspiration from Uber's success and attempting to replicate its disruptive model. Even more than the Uber story, the approach TK had to building companies was noteworthy. It soured for reasons I would debate at other times, but he changed the approach. Like artists, though, as time went on, it became clear in the market that building the 100th "Uber for X" platform would not bring about substantial change. The trend that Travis Kalanick started played out, revealing the limitations of merely imitating a successful concept.
Now, history seems to be repeating itself with the rise of "AI for X" startups. While OpenAI has opened up exciting possibilities, many of these ventures have become mere copycats, trying to capitalize on the AI trend without truly innovating. There are now 12 companies fighting for a piece of NVIDIA’s evergrowing pie, and likely 25 trying to build a better ChatGPT. Many founders are now doggedly pressing the issue of integrating AI into their core products, and it feels forced in many cases. However, amidst the sea of imitators, there are still innovative AI tools emerging that deliver on the promises of artificial intelligence, addressing the desires and needs of users in unique and meaningful ways.
Magnetic Framing
One of the daily newsletters I enjoy reading is Matt Levine's Money Stuff Newsletter. It's entertaining, and I never feel overwhelmed by the topics covered. Last week, he discussed an intriguing story about an obscure tax credit investment strategy that caught my attention. One of the points he made is how this fund has set itself apart, which is crucial. I believe that now, more than ever, it is important for founders, fund managers, or anyone raising money to differentiate themselves.
Here is a quote from his January 2 edition of Money Stuff, where he speaks about an obscure tax receivable agreements firm called Parallaxes Capital:
"As Lee pitches TRA holders, he educates potential investors. 'I got the deck sent to me and at first I didn’t really understand what this was,' said Gilbert Calderon, chief investment officer at M4 Capital Management, a single-family office in Chicago known for buying esoteric investments. M4 eventually signed on."
"That's what you want! 'I got the deck sent to me and at first I didn’t really understand what this was.'"
"I mean in the sense that you might be getting an uncorrelated source of returns, but also in the sense that you will have a little treat, some entertainment in your workday, a pitch meeting that, for once, will feel new."
Again to reinforce this idea, Rick Rubin expresses a similar sentiment in Creative Act:
"A painting is just a painting until you put a frame on it and hang it on the wall, then it’s called art." — Rick Rubin
Rick Rubin suggests that a painting becomes art when it is framed and displayed. This insight teaches entrepreneurs the importance of framing their ideas, products, and services in a way that adds value and resonates with their target audience.
How something is presented can greatly impact its perceived worth and impact. This quote succinctly captures the essence of framing and presentation in transforming something ordinary into something of value and significance. It highlights the idea that how something is presented can greatly impact its perceived worth and impact.
Financial Mastery
As we prepare for what will undoubtedly be another intense presidential election in 2024, I found myself bored during the holidays and decided to read Dark Towers: Deutsche Bank, Donald Trump, and an Epic Trail of Destruction. Although it did not provide me with concrete evidence that Donald will end up in jail, the book did shed light on the complex relationship between Donald Trump, Deutsche Bank, and the Kushner family.
Jared Kushner and his brother Josh have been making more frequent media appearances in recent months. There is much to learn from both of them as entrepreneurs and investors. I do not have a particular opinion, but I have found their conversations on Lex Friedman's Podcast, the All-In Podcast, and Invest Like the Best interesting, perhaps because neither of them has done much press.
While the main point of the book is to emphasize the importance of understanding the potential risks and consequences of engaging in complex financial arrangements, the most fascinating aspect for me was how Jared used his relationship with Trump to secure a $15 million credit line to kickstart the family’s empire after his father did time in federal prison.
"Jared’s father had been convicted of tax evasion and witness tampering. Even at a lender as uninterested in its clients’ reputation as Deutsche was, the family patriarch’s incarceration had made the entire family essentially off-limits. But Vrablic and Ivanka had grown tight—they weren’t quite friends, but they saw a lot of each other at social events—and she’d known Jared Kushner since before her arrival at Deutsche."
It is important to note that this is not definitive evidence, but I find it ironic that the Kushner empire was restarted for both Jared and his brother Josh, and all that they have done would not have been possible without Donald Trump's relationship with Deutsche Bank.
Perfect Timing
Bible readings emphasize the importance of timing, faith, and purpose in one's journey. I have once again started my yearly challenge to read the Bible in a year. Though I have never met the goal, the challenge is always enticing. Ecclesiastes reminds us that there is a time for everything, emphasizing the need to recognize and seize opportunities when they arise.
A Time for Everything — Ecclesiastes 3:1-8
[1] For everything there is a season, and a time for every matter under heaven: [2] a time to be born, and a time to die; a time to plant, and a time to pluck up what is planted; [3] a time to kill, and a time to heal; a time to break down, and a time to build up; [4] a time to weep, and a time to laugh; a time to mourn, and a time to dance; [5] a time to cast away stones, and a time to gather stones together; a time to embrace, and a time to refrain from embracing; [6] a time to seek, and a time to lose; a time to keep, and a time to cast away; [7] a time to tear, and a time to sew; a time to keep silence, and a time to speak; [8] a time to love, and a time to hate; a time for war, and a time for peace.
This week’s insights highlight the significance of embracing creativity, effectively framing ideas, understanding financial complexities, and recognizing the importance of timing, faith, and purpose. Thank you for taking the time to check out the Four Insights newsletter.
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