3 Posts I Wish I Would Have Written

The best ideas in entrepreneurship and business finance rarely originate from a single source. One hallmark of a sharp operator is the habit of reading widely, synthesizing ideas from adjacent fields, and crediting the thinkers who got there first. This post captures exactly that spirit.

Unfortunately, there's not enough time in the day. For some of us, there aren't enough ideas in the can to create some of the best content out there. Sometimes I'm absolutely jealous of what others produce when they write. It's like they're masters at work in their use of the English language. I'm menial at best, but in my online reading, I find stuff that's often too genius, funny witty or--most importantly educational--that I wish I would have come up with the idea first.

In some cases, I did, but I failed to be the first to codify it on paper. Here are a few written or video posts from the week I wish I could claim as my own.

Risk Mitigation, Not Risk Taking: The Entrepreneurial Mindset

1. This is from the genius of Tim Ferris--in this case, from one of his guests--on how entrepreneurs are actually better at risk mitigation than risk taking:

Far from being one of the world’s great risk takers, Bill Gates might more accurately be thought of as one of the world’s greatest risk mitigators. And in that, he is not alone. The simple fact is that everyone is afraid of risk at some level...

While this post is older than the next two and does not involve video, it perfectly describes how I approach entrepreneurship--to a T.

This framing matters enormously in the context of M&A and capital markets. A business owner preparing for a transaction is not swinging for the fences on pure optimism — they are systematically reducing the unknowns a buyer or lender will price against them. Understanding what causes deals to fail is itself a form of risk mitigation: the founder who has studied failure modes walks into a process far better prepared than one who hasn’t. If you’re building toward a liquidity event, the sell-side preparation workflow is a practical starting point for mapping and reducing your own deal risk before engaging advisors.

Marketing Without Shortcuts

2. In this video blog by local Seattle-ite Rand Fiskin, he discusses all the wrong ways to market. His stuff is always cogent and evergreen, but this one particularly hit home and went VERY well with #3 below.

Rand’s critique of shortcuts maps directly to how sophisticated buyers evaluate businesses in a transaction. A company that grew revenue through gimmicks — inflated trial conversions, channel stuffing, affiliate dependency — will face hard questions in due diligence. Authentic, repeatable demand generation is a quality-of-earnings signal. Buyers and their advisors will reconstruct your revenue story; the version you’ve built with integrity holds up under that scrutiny far better than one assembled opportunistically.

Execution as Identity

3. Fred Wilson, threw up an interesting interview from theBlaze.com with Gary Vanerchuck.

I spent the whole 40 minutes of the interview eating it up and finding more ways to improve. If you get a chance to watch the video, I recommend it. I’ll include it below, just in case. Gary himself is a little hyper, which I love. It shows how he’s able to just get things done. Love it. The principles he discusses are spot-on.

The throughline across all three resources is deliberate execution. Whether you’re building a business to operate for decades or positioning it for a strategic sale, the fundamentals are the same: manage downside risk, build authentic momentum, and execute without shortcuts. For a structured look at how those principles translate into transaction readiness, the investment banking guide offers a practical framework grounded in the same philosophy.

Loved each of these posts I picked up in my feed reader this week. I wish I could have been brilliant enough to come up with their content. Perhaps another day when I have more time.

Frequently Asked Questions

Why does risk mitigation matter more than risk tolerance in business transactions?

In a sale or capital raise, buyers and lenders price uncertainty. Every unresolved operational, financial, or legal risk becomes a discount applied to your valuation — or a reason to walk away. Founders who proactively identify and address those risks before a process begins command better terms and close more reliably than those who simply tolerate risk and hope for the best.

How does marketing authenticity affect a company’s value in due diligence?

Quality of revenue is one of the first things a sophisticated buyer examines. Revenue driven by genuine customer demand, low churn, and repeatable channels carries a meaningfully different multiple than revenue assembled through one-time promotions or channel dependencies. Advisors will reconstruct your customer acquisition history — how that story reads has a direct impact on valuation and deal structure.

What resources can help a business owner understand the deal process before engaging an advisor?

Starting with a clear picture of how an owner might approach selling their company is a useful orientation. From there, the transaction preparation overview outlines the key stages and workstreams involved in bringing a business to market, whether the goal is a full sale, a recapitalization, or a minority capital raise.