Advanced Pitching Skills: Avoid the 9 Worst Thin Spots

Adapted from a piece that originally appeared on The Seraf Compass.


If you want to get through a demo day or pick up a few seed investors, you can do it by covering the basics. But if you want to raise serious money, you are going to have to dig deeper into your bag of tricks and address some of the advanced issues. These are the critical areas where pitches are almost always too shallow. Knowing which are the trouble spots and how to make sure they are covered is essential advice. Let’s go through them one at a time.

Explaining The Market Moment

To be credible, a pitch must answer the “why you, why now?” questions that provide context for the business. What has changed in the universe that makes this business suddenly not only possible, but a great idea? An entrepreneur must explain why they are the gal or guy to do it.

Detailing The Go-To-Market

An entrepreneur has to be specific about how they are going to crack their market. Selling is really hard, especially to certain types of customers. They are going to need to convince investors that they have a very specific and detailed plan or business model innovation that is going to allow them to acquire their intended customers affordably (relative to their lifetime value).

Assuming Fast Consumer Behavior Change

Making assumptions about how target customers’ behavior is magically going to change has been referred to as “delusional economics.” After the few early adopters, mainstream customers have incredible inertia. The power of the status quo can be immense. The arrival of the internet/wireless/mobile is not going to suspend the laws of physics and gravity in an entrepreneur’s industry. It is not safe to assume that if they build a more efficient clearinghouse / marketplace / trading platform / matching service, everyone’s behavior will instantly and automatically change. Convincing customers to buy from them is going to be hard and expensive. They need to explain what secret sauce makes it less hard.

Paying Insufficient Attention to Buying Priorities

Certainly someone will want an entrepreneur’s product. Unfortunately, their immediate addressable market is limited to the people for whom buying their product is a top priority. How many of them are there? Although a lot of businesses identify a real, legitimate problem for customers, they still fail because other higher priority problems gobble up customer wallet share.

Omitting Marketing Skills

When talking about their go-to-market, entrepreneurs either need to convince investors that they have the marketing experience on the team, OR that they know they don’t and they plan to go get it. Everyone thinks they know how to market. Most don’t. Entrepreneurs need to identify the marketers who can help them.

Building a Realistic Model

Most entrepreneurs totally underestimate what it will cost to achieve success. Investors have seen and experienced many business models and know it is always harder, takes longer and costs more than anticipated. It is crucial to really think through the necessary people, time and financial resources required, and to come prepared with a realistic plan. Entrepreneurs should use both a bottom-up and a top-down approach. Then sanity check it against benchmarks. Underestimating costs and showing an improbably fast time to big revenue and profitability doesn’t impress people with the model – it highlights the naivety.

Assuming It Will Translate

Even if an entrepreneur can paint a credible case for their initial target market, don’t assume that the next vertical, next geography or next customer segment will be as easy. Logic dictates that they are starting in the easiest place. By definition, any expansion will be harder and farther out of their comfort zone and experience base. They must be realistic about their expansion assumptions. Yes, their brand and momentum will help a little, but nowhere near as much as they think (see Build a Realistic Model).

Engineering a Sustainable Competitive Advantage

Even if a company can fight to win a segment, if it cannot make any money at it over the long haul, they’ve still lost. Too many entrepreneurs talk as if their market is standing still, when, in fact, any market worth tackling will always be evolving and growing more competitive. It is critical to talk about how they will defend their position, their pricing, and their margins against the inevitable competitive reactions. It might be intellectual property, it might be some kind of tolerable customer lock-in or switching cost, it might be a product roadmap that keeps their value prop more compelling over time. Whatever it is, they need to explain it, and the explanation needs to be believable.

Failing to Think Exit Scenarios Through

Most entrepreneurs don’t think through their exit strategy adequately. If they succeed, who buys them? Ultimately this is the bottom line for investors. Equity from investors is like a loan that the buyer of their company pays back. They need to talk in detail about the different classes of buyers, why they would buy the company, what they would value it for, what kinds of multiples they might be expected to receive, and what milestones they will need to hit to command those prices.

It is not easy for an entrepreneur to step back and look at their story objectively enough to spot where it is thin. But there are a few critical big-picture elements they simply cannot afford to blow past. Their job is to make sure to cover the above topics adequately—this is the key to convincing investors that the company and team is one that just might reach exit velocity and escape rather than fall back out of orbit and burn up on the way down.

Seraf Co-Founder Christopher Mirabile is the chair of the Angel Capital Association and also Co- Managing Director of Launchpad Venture Group. He has personally invested in more than 50 startup companies and is a limited partner in four specialized angel funds. Mirabile is a frequent panelist and speaker on entrepreneurship and angel-related topics and serves as an adjunct lecturer in entrepreneurship in the MBA program at Babson.