The puzzled look on a first-time founder’s face after hearing an investor’s concern of a “messy cap table” happens more than some probably think.  But what the heck does “messy”…

Something is wrong. 20 initial meetings is almost never enough to fully complete a round of funding. But 20 meetings with the right investors should result in at least a…

The value of this article will be directly proportional to the significance of a market downturn that creates general uncertainty and affects the ability for startups to fundraise.  All downturns…

I think of due diligence as an investor’s process for confirming either their intention or full-blown commitment to invest in your company. After initial conversations, presentations and email exchanges, a…

The COVID-19 pandemic forced all interactions between investors and fundraising founders into virtual settings.  And the return to a “new normal” will certainly leave a place for them into the…

For much of my career, a one-hour meeting was the norm.  But in the world of startups, 30 minutes is all you get most of the time for sessions with…

Some of the posts to this progressively-built article no longer apply, and that’s a good thing because it means investor and fundraising dynamics have returned to normal. I never imagined…

Founders often ask me how much revenue they need to generate to be ready for a Series A.  The question is so common that I previously wrote an article just…

Just from the article’s title you probably think you know everything I’m going to say, right?  I predict not but soon we will find out.  The basics definitions of aspirations,…

Raising money from professional investors before your product is built, launched and generating revenue is far more difficult than when those things have already been accomplished.  This can result in…

Investors are often skeptical of claims made by startup founders.  Among the various types of claims that can be made, this especially relates to all forms of traction.  This article…

I often get asked how much revenue is needed to successfully raise a Series A.  I can tell the entrepreneur wants me to confirm what they might have read in…

I know, you just want me to show you the scorecard and associated secret formula investors use to decide a supposedly “fair” valuation for your company.  Unfortunately, you are only…

With as little as it costs to get a software startup off the ground these days, many entrepreneurs start off as what we call “bootstrappers” rather than fundraisers.  There’s nothing…

Not much different than the famous chasm described in Geoffrey Moore’s book “Crossing the Chasm”, funding your startup venture over time also has a chasm that you want to avoid. …

When I ask entrepreneurs what their most valuable resource is, I ALWAYS get one of two responses: money (aka – funding, cash) or people.  And it’s hard to argue about…

Almost no investor wants to be the “first check written” for your round of funding.  This makes total sense if you think about it from their perspective.  If you don’t…

Here’s a scenario I commonly see.  A startup raises $1M in total seed funding to turn their MVP into a real product and figure out a profitable and scalable customer…

I didn’t invent this quote (can’t remember where I heard it) but what a great one to help remember that with most business-related transactions, price is definitely not the only…

FINALLY!!!  After years of waiting for equity-based crowdfunding rules (aka Reg CF) to be adopted and put into effect following legislative approval of the JOBS Act of 2012, it’s finally…

I’m not talking about a stand-up presentation in front of an individual investor or VC firm but rather some form of on-stage pitching event.  It might be called a “demo…

While you are still in the idea phase, investors tend to focus on vision, promise, potential and personality traits of the founder(s) because that’s all you have for them to…

Most startups think of a convertible note as the most common fundraising vehicle used during the pre-seed and seed stages (see related article titled “Convertible Note Basics“).  What they might…

Every field of study has its basic vocabulary of words and phrases that come up over and over again. This vocabulary is so fundamental that it is used to explain…

In a previous article, I described various ways to determine how much money to raise (you can read it here).  If you’ve decided and communicated how much you are raising, you might…

If you aspire to build a company that is scalable, then the size of your market is a very important element of your business plan. That’s because it suggests the…

Let’s assume you have already determined $500K is the ideal amount of money to raise in your current fundraising round (see related article titled “How Much Should You Raise”) and…

You didn’t plan for it to happen this way but you’re reaching the maturity date (end of term) on your convertible note and didn’t raise money in an equity round…

You’ve just completed a great investor pitch with heads nodding and good interaction.  You’re about to ask “Does this opportunity interest you enough to explore an investment?” when instead you get…

Similar to the “So What” rule, every time you make a claim, prediction or forecast, imagine your audience is thinking to themselves “yeah, right!” in skeptical fashion immediately after seeing/hearing your…

Initially made available by Y Combinator (YC) in 2013 and subsequently updated in late 2018, the SAFE investment instrument was intended to improve on the highly popular convertible note used…

Once you have a product in the market with an increasing number of paying customers, your valuation will increasingly be driven based on financial and operational metrics.  Don’t get me…

There’s a reason it’s referred to as an “elevator pitch” – it must be expressed in a few sentences and no more than 15-20 seconds.  And that might even be…

Each individual investor and venture fund is different in the way they like to interact during their investment evaluation. This difference is pronounced amongst angel investors and less so for…

In a previous article I explained what convertible notes are and when they are commonly used (see article titled Convertible Note Basics).  Now I’d like to dive into one of…

Hopefully you are reading this before you decide how much to raise.  I’m referring less to the earliest funding raised (perhaps from friends and family) just to get your minimum…

Storytelling is a powerful skill for any great communicator.  When told well, a story helps us best absorb a message and its meaning.  It can make the difference between remembering…

Your pitch deck will become the single most valuable communication tool to use with external audiences of all types and you will use it for multiple purposes. You’ll definitely use…

Are you scratching your head trying to figure out how convertible notes work?  They are form of convertible security that is so commonly used for pre-seed and seed rounds of…

If you're fundraising during the very early formation of your company, your ability to predict the future will be very difficult.  Of course, you can imagine and dream what might...

I recently heard Dr. Robert Wiltbank from Willamette University use this analogy and loved it so much I had to share it with others.  Entrepreneurs are, by nature, very optimistic. …

Some investors seemingly take forever to make a decision. But if you think about it, if they can stretch out the timeline for their evaluation and initial due diligence, they…

Fundraising is rarely easy and is usually a far underestimated undertaking by entrepreneurs that haven’t done it before.  In the fundraising section of this blog, I describe ways of approaching…

Here’s the scenario. After securing your first investors and then having a flurry of activity over a couple of months (see related article titled “The Domino Effect of Fundraising”), you…

Fundraising can seem like herding cats.  You get some initial momentum, potentially from a pitching event, and have a bunch of conversations but can’t seem to get the funding commitments…

I use this rule all the time when advising startups and early stage companies.  It has all sorts of sales, marketing and fundraising application, regardless of your company’s stage.  I…

Pitching events (often called “demo days”) are prevalent these days.  There’s possibly too many of them for active startup regions, which results in fatigue on the part of investors looking…