Thoughts on startups by investors that
fund them & entrepreneurs that run them

Blog Archives

Convertible Debt: Worst Form Of Seed Financing — Except For All The Others

How to finance a new seed-stage startup?  Equity?  Convertible debt?  Convertible equity?

As of August 2010, Paul Graham famously proclaimed, “Convertible notes have won. Every investment so far in this YC batch (and there have been a lot) has been done on a convertible note.”  Yet in my little corner of Wonksville, Founder Institute CEO Adeo Ressi and Yoichiro “Yokum”

Read more >

Second-Class Investor Citizens: Facebook’s IPO and Dual-Class Equity Structures

Dual-class voting structures are receiving a lot of attention these days along with intense publicity related to the Facebook IPO, following in the wake of other recent tech IPOs with a similar structure such as Zynga and LinkedIn.  This is nothing new; long favored by family-controlled media empires such as Rupert Murdoch’s News Corporation, among Internet firms alone, Google took

Read more >

The Problem with Private Placement Memorandums (PPMs)

The sale of equity in private companies is regulated by the Securities Act of 1933, which requires that the company either register with the SEC or meet one of several exemptions (Reg D).  A Private Placement Memorandum (PPM) is a special business plan defined to meet an SEC exemption.  In most cases, those entrepreneurs choosing to raise capital using PPMs

Read more >

The reality of returns on angel investment

Editor’s note: This was originally a question and answer on Quora, but the community response was so significant we decided to syndicate it on our Gust blog.

Q: If I want to invest $5,000 as a new angel investor into a new company or companies as part of an angel syndicate, what chances do I have of making a profit in 5 years?

Read more >

Average Round Size in Angel Deals

The Center for Venture Research at the University of New Hampshire has been publishing statistics on angel investing for decades.  Over the past several years, the numbers of US companies funded by angel investors has increased from about 50,000 per year to over 60,000 annually.  Mark Boslet of senior editor with Venture Capital Journal posted the following chart on peHUB,

Read more >

Good Sources on the Pros & Cons of Convertible Notes

Entrepreneurs: if you’re looking seriously at angel investment, and you have the kind of product-market fit and management experience investors will like, you need to take a good look at convertible notes.

Do yourself and the investors you want to talk to a favor: take a few minutes and do some homework on this issue.

Entrepreneurs: Due Diligence on Investors is Smart

Due diligence should always be a two-way street. A while back, I published an article on “Startup Due Diligence Is Not a Mysterious Black Art,” describing what investors do to validate your startup before they invest. Here is the inverse, sometimes called reverse due diligence, describing what you should do to validate your investor before signing up for an equity

Read more >

Trends in Seed Stage Funding for Entrepreneurs

I’ve recently taken a look at seed stage funding by venture capitalists (VCs) and angel investors over the past five years.  For VCs, I chose to look at all seed stage VC deals (from MoneyTree©) as well as those in five of the most active regions in the country.  Note that I merged the two Southern California regions (LA/Orange County

Read more >

Keep Term Sheets Simple for Quicker Cash to Spend

Remember a term sheet agreement is not a deal until the check clears. Entrepreneurs sometimes assume an initial agreement with an angel is a commitment, so they start spending before any money is received.  Due diligence and paperwork take time, and can change everything.

Knowledge Is Power: Convertible Note Financing Terms, Part III

Last week, we took the plunge and began dissecting an example term sheet for a convertible debt financing round piece by piece.  I’ll continue with more specific terms and wrap up next week with some thoughts about recent changes and trends for the future. Readers may find it helpful to download the sample term sheet from my firm’s website and

Read more >