Entity Type
Forming an Entity (LLC v. C-Corp)

This blog was originally published in March of 2018 but was revised in January of 2025 and is still accurate. Okay – it’s time to actually form the business. You’ve built your pitch deck, received feedback from naysayers, visited with […]


Funding & Capital Raising
How Founder “Vesting” Really Works

Vesting is the process whereby a recipient of equity earns the equity, or the right to purchase it in the case of options, over time. As I mentioned in my last post, the typical schedule is 4 years with a 1-year cliff. […]


Funding & Capital Raising
Everyone Should Vest

One of the biggest mistakes that startups make is failing to place vesting conditions on founders’ equity. Here’s an example: Two founders, Adam and Blake, are working on their startup, and everything is butterflies and rainbows. They have a great […]


General Business
Make An Investment In Legal

A question I often hear from startups when discussing initial legal work is, “How much will this cost?” This is the wrong question – most startups are looking at their legal expense the wrong way. They should be asking, “How […]


Pitching/Decks
Find Some Naysayers

A common mistake that I see aspiring entrepreneurs make all too often is failing to find anyone who will challenge their idea. I addressed this in my review of Silicon Valley S3, Ep7. Affirmation from loved ones is often a […]


Pitching/Decks
Pitch Decks Are The New Business Plan

Back in the day, like, the early aughts, it was widely believed that you needed a 20 to 40-page business plan and 40-80 hours to create it. The business plan was a written record and forecast of your idea, replete […]


Intellectual Property
Your Idea Is Worth Nothing

“I’ve got this great idea…” How many times have you heard that? For me, it’s weekly, if not daily. But no one makes money on an idea. As a founder, you have to realize that ideas are easy, they are […]


General Business
What’s The Difference Between A Small Business And A Startup?

What’s the difference between a small business and a startup? Structurally – a lot. Operationally – not much. And I’ll explore that throughout this series. To me, startups are a subset of small businesses. They are both initially owned by […]


General Business
If I Were Starting A Business…

There has never been a better time to start a business. The power of the internet coupled with plummeting startup costs (and if you’re in the US – advantageous tax regulations) creates the perfect backdrop for anyone looking to start […]


General Business
Hosting a Board Meeting? Here’s how to do it well.

Board meetings are essential to running a startup. While formal meetings are often neglected during the early stages of a startup, they quickly become a required quarterly event once a startup accepts institutional capital. Hosting the company’s first board meeting […]