Hey everyone,
Matt here and returning from a week off of sharing with you all, do not worry you will be getting more from the Stretch Four Newsletter in the coming months. Welcome to our new subscribers.
This week, I am introducing the Four Thursdays Edition of the Stretch Four Newsletter! Each edition will focus on actionable insights and practical advice on personal finance, health, productivity, parenting, and more. Each issue will cover four topics, one for each Thursday, including a question, quote, learning, and essay. I will also share book recommendations, articles, and resources for further learning. Four Thursdays is a passion project, and I hope it becomes a valuable resource for you to improve your knowledge and skills in various areas of life.
Question: Is the mid-to-late 30s the perfect time to start something new?
Quote: "I don’t have anything in common with people who stand on escalators. I always walk up to them — why waste time? You have eternity to rest when you die." — Michael Bloomberg, on escalators
Learning: Starting families and running startups
Essay: Enterprise sales cycles and casting visions
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Let’s dive in.
Is the mid-to-late 30s the perfect time to start something new?
As I approach the age of 36, I find myself thinking about starting something new. Although I sometimes wonder if my energy is waning and if I have any good ideas, I also feel more creative than ever. Additionally, I believe that I am better equipped to avoid potential pitfalls and reduce the risks associated with new ventures. Nowadays, I spend most of my professional life reflecting on past experiences and striving to make rational decisions instead of being driven by emotion. I try to understand things in ways that I wish I had seven years ago.
This response does not answer the question directly. However, Harvard's 2018 research sheds light on the age of successful startup founders. While it is difficult to define what constitutes success, the findings are insightful. The trend in the startup world is to favor youth, but the reality may be different. Reid Hoffman, for example, founded LinkedIn at the age of 36, and it eventually sold for over $20 billion. It would have been very difficult for a 20-year-old to start a company like LinkedIn. I believe that there will be a surge of groundbreaking companies and ideas from my millennial friends, given the rapid changes in how we parent, work, and grow old over the past decade. When this is paired with the wealth that our parents will leave behind, the next 20 years will likely bring significant developments. I am optimistic about the mid-to-late thirties builders so if you are building something please reach out.
Michael Bloomberg, on escalators
I don’t have anything in common with people who stand on escalators. I always walk up to them — why waste time? You have eternity to rest when you die. — Michael Bloomberg, 2014
Lately, there has been an obsession with the white billionaire class — the media is fascinated with Elon Musk, Jeff Bezos, and Mark Zuckerburg. I find myself taking a contrarian approach to reading biographies about some that are not as widely documented. Michael Bloomberg built what may be the most successful technology product of all time with the Bloomberg Terminal. He has had multiple acts, including politics, climate change work, and longevity (he wholeheartedly believes he will live to 125 years old). I thought this quote was a great way to start the book I recently read The Many Lives of Michael Bloomberg.
In addition, to add more context to our question of the week, Michael Bloomberg shared his experience of starting something new at 39 years old. Although he did receive a $10 million going away gift from his employer, building an enterprise that is now likely worth $70 billion after one's 39th birthday is still impressive.
Starting families and companies
During a conversation with a fellow founder last week, we discussed the challenges of balancing family life with being a startup founder. As my wife Whitney and I prepare for the arrival of our second child in less than two months, I advised him to hold off on starting a family. While I love my son Cain and look forward to his little brother's arrival, I had to be honest that parenting, marriage, and other commitments can conflict with the amount of time required for a startup to succeed.
Now that I am a parent and husband, I have come across many stories of successful entrepreneurs who started families before they arrived. For instance, Isadore Sharp, the founder of Four Seasons, could not afford luxury vacations until his children were older after getting married and having three children right away.
*Three children, a couple still in diapers, in an apartment with only two bedrooms—our situation was not only a drain on income but on time. And I had neither the knowledge, judgment, nor time to become a good parent. I was working morning till night, six or seven days a week, so with few qualms, I left the upbringing of our children, along with the care of our house, to Rosalie. Rosalie never complained, never tried to change me, though she once left me a note so succinctly pertinent that I still keep the original in my notebook: “Overachievers suffer loss of intimacy. No time for fun. Relationships starve on a diet of self-absorption. Home is the place to express the playful part of oneself.” — Four Seasons: The Story of a Business Philosophy
He went on to build one of the most well-known luxury brands in the world, but there was clearly no ideal time to start a family when you have that type of ambition.
Enterprise sales cycles, and casting visions
Recently, I visited the headquarters of a major prospect, which got me thinking. As startups increasingly focus on revenue, my business, like others, has become more interested in enterprise customers.
These customers have the budget and stability to build long-term relationships. Therefore, if you want to increase revenue, it makes sense to sell to these larger companies.
While this approach is practical, someone from our prospect's corporate venture team suggested a different approach. He advised us to approach the company as both a learner and an educator.
The non-obvious thing about selling to enterprises is the sales cycle. As deals grow larger, complexity increases, making outreach, outbound calls and emails, and content necessary. For example, a machine learning company CEO recently shared on a podcast that he is lucky to get three customers on the phone a week, and anyone who quotes more than that on average is lying.
Most founders and founding teams do not account for the buying process, which requires wearing many different hats. Additionally, each enterprise has its own unique needs, and there is a limited timeframe for an enterprise customer to open their checkbook, evaluate your product, or pilot your solution.
The advice I took away is to prioritize being a learner and getting deeply involved in the buyer's needs, rather than just trying to build transactional relationships. While it's important to gain customers and generate revenue to validate your startup, taking a transactional approach at the enterprise level will likely lead to churning through countless relationships.
This process involves conducting research to determine when the prospective buyer is able to make a purchase, establishing backchannel connections across knowledge spaces, and ensuring that you can build a product that is at least 10 times better, or convincing them that you can.
The next step is to educate the enterprise on why your product makes sense for their business. While everyone talks about the importance of "product-market fit," this concept does not necessarily apply in the enterprise space. These companies have options, and they do not have to purchase your product.
One unique advantage of being immersed in the Bay Area tech echo chamber is that many large enterprise decision-makers in industries like financial services and insurance are not located here. However, when you enlighten them on what is happening and how tech companies operate, they can become enamored with it because it is unique and fascinating to them.
Developing these two skills is more important than focusing solely on hardcore transactional pilot pushing, which is the norm for most founders.