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A newsletter about entrepreneurship and finance

Damian Olive
Oct 2, 20244 min read
Constellation Software, growing through acquisitions
“Think of the small as large, accomplish the great task by a series of small acts.” Lao-tzu, 4th century BC Making the impossible happen...

Damian Olive
Oct 2, 20244 min read
What lower rates mean for entrepreneurs
What happened Last week the Federal Reserve cut interest rates for the first time since the pandemic. The larger-than-expected 0.50%...


Damian Olive
Sep 13, 20243 min read
Building a Monster Business
In 2004, I bought shares of United Rentals at $15 a share. In less than two years it doubled and I sold at $30. Shortly after that the...


Damian Olive
Sep 13, 20244 min read
How great CFOs make difference
The CFOs of two large technology companies, Google and Salesforce, recently announced that they would be leaving their roles. Both Ruth...

Damian Olive
Aug 29, 20244 min read
Does your company need external capital? A simple way to think about this
This is intended for entrepreneurs and business owners who are evaluating the possibility of raising a new round of equity from outside...


Damian Olive
Jul 23, 20243 min read
Valuing your business: it's not always about the numbers
Entrepreneurs often get financial tunnel vision, focusing intensely on revenues, profit margins and growth projections. While these are...


Damian Olive
Jul 17, 20242 min read
Can entrepreneurship give you freedom, or is it the perfect siren song?
The promise of entrepreneurship is that it can bring fame, fortune and freedom. A blank canvas where you can choose goals, create...


Damian Olive
Jun 24, 20244 min read
How Elon Musk combines entrepreneurial energy with an investor’s mindset
Starting a business can be intense. Building something from nothing requires speed, creativity and courage. That’s why entrepreneurial...


Damian Olive
Jun 6, 20245 min read
The Pit Bull Incident
I’m going to link this to entrepreneurship eventually, but please bear with me. This happened two days ago. A typical spring morning,...

Damian Olive
May 28, 20245 min read
The biggest pain points for entrepreneurs right now
In recent conversations with entrepreneurs and business owners, two main challenges stand out: Growing without external capital...


Damian Olive
May 23, 20245 min read
Making progress in tough times
The great boxer Muhammed Ali was once asked how many sit ups he could do. He replied that he didn’t know because he only starts counting...

Damian Olive
May 15, 20244 min read
What if you never raise another round?
Cyclical Forces The landscape for startup financing has shifted dramatically in the last 3 years. From the peak of 2021, when zero...


Damian Olive
May 7, 20244 min read
Warren Buffett's Wisdom of a Lifetime
Berkshire Hathaway held its 2024 shareholders meeting last Saturday. It was the first meeting after the passing of Charlie Munger, Warren...


Damian Olive
Apr 29, 20243 min read
How much revenue growth do you really need? Less than you think
Myth: you need hyper growth in revenues to generate extraordinary returns for your shareholders. Reality: you don’t. VC funding and its...


Damian Olive
Sep 20, 20234 min read
Are brand aggregators viable?
Companies buying brands that sell primarily through ecommerce channels recently raised $16 billion in new capital. Most of that was in...


Damian Olive
Apr 2, 20232 min read
How acquirers evaluate brands
When acquiring a brand, there are a number of factors that buyers look for. Here are some of the most important ones: Price range Buyers...


Damian Olive
Apr 1, 20233 min read
Preparing your business for a sale
Selling an ecommerce private label brand can be a great way to cash in on your hard work and investment. However, it's important to be...


Damian Olive
Mar 23, 20234 min read
What we've learned about paid advertising
We approach paid marketing as an investment operation. Our goal is to achieve attractive returns on the capital that we invest to promote...


Damian Olive
Mar 22, 20232 min read
Evaluating your financial performance
Private label ecommerce brands are a popular way to start a business. They offer a number of advantages, including low start-up costs,...
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