How to sell as a founder when you've never sold: what investors see from the other side of the table

45 hours a week on the other side of the table

When I was Chief Commercial Officer of a crypto VC and accelerator, I spent on average 45 hours a week listening to founders pitch.

Some of them were clearly very skilled salespeople. They communicated their idea well and they were very persuasive. That didn't mean they always got what they wanted: that depends on full due diligence. But it increased their chances of success by a large margin.

Most of them were not good. Most of them were terrible. They got bogged down in details I didn't care about. They lost my interest. They didn't change direction when I asked them questions. And if we got as far as negotiating, they negotiated badly.

Why are most founders bad at selling?

It isn't surprising. Many founders, perhaps most, come from a technical background. They can build something great because they have real expertise in their field. Selling was never part of that training, and for a lot of them it doesn't come naturally.

So what happens? They often give away half their equity to someone just because that person can sell for them.

But what if they learned to sell themselves?

Do investors judge how well a founder sells?

Yes. When I sat on the other side of the table, I made a mental note of every mistake a founder made. Trust me: as well as assessing the business, you're assessing that person's ability to sell. If you can't sell your company to an investor in the room, it's fair to ask how you'll sell it to customers, hires and your next round.

A mediocre idea championed by a great salesperson is always more attractive than a great idea championed by someone who can't explain it properly.

I remember one founder who had one of the best product-market fits I'd seen, one of the best MVPs, a great deck, and excellent early user numbers and feedback. But he could barely string a sentence together, and he couldn't answer our questions at all.

We told him to come back once he'd found a non-technical co-founder. His missing ingredient was sales skills, and we couldn't back him until he had them.

Don't be that guy.

What does a founder who can sell look like?

I remember one call with a founder who had a great product and serious traction already. He never even showed me a deck.

The first thing he did was move the call onto ground that suited him. "Great to meet you. I'd love to just have a chat. Tell me about your time in web3." He knew we'd like what he was building, so he had the leverage to do it.

We talked for over an hour. I pushed back my next call. We covered everything, and it was like talking to an old friend who also happened to be an entrepreneur. But over the course of that conversation, he didn't fail to give me every piece of information a deck would have contained. It was masterful.

You can imagine the power he had when it came to negotiating the term sheet we inevitably offered. In the end he didn't even need us: he'd already oversubscribed his seed round.

Look at what he did:

• He set the frame. A conversation, not a presentation. I was talking about myself within a minute, and I was enjoying it.
• He used his leverage. His traction meant he didn't need to perform for us. He knew it, and he let it show without ever saying it.
• He still covered everything. The relaxed conversation was a structure. Problem, product, traction, team, the raise: it all came out, in the order my questions led him.

The four mistakes I saw in most founder pitches

1. Getting bogged down in detail

Founders love what they've built, so they talk about features: features, features, features. The investor (or the customer) doesn't care about your features until they understand the problem and why it matters to them. Lead with the problem and the solution. Bring in the detail only when it backs up a point they already care about.

2. Losing the listener

A monologue loses people. You can see it happen: the eyes go to the phone, the questions stop. Make your point, then ask a question. It keeps them in the conversation, and their answer tells you where to go next.

3. Not changing direction when they ask questions

A question is the listener telling you what they care about. Most founders answer it briefly, then go back to slide nine. Answer the question they actually asked, properly, and follow where it leads, even if that isn't the next thing in your deck.

4. Negotiating badly

If you get to the term sheet, or to pricing with a big customer, you're in a negotiation, and the other side has usually done far more of them than you have. Know before you walk in what you want, what you're willing to trade and where you'll walk away. Never give something without getting something back. And make sure you're fighting about the right things.

What do founders get wrong when negotiating a term sheet?

So many founders focus on completely the wrong thing. They obsess over one particular clause and its wording. I've had hour-long conversations about governing law and jurisdiction, or the wording of a non-disclosure clause.

It's not that those things don't matter at all. Sometimes they do. But they matter far less than the commercial terms.

For an experienced contract negotiator, it's an absolute blessing when a founder anchors the whole negotiation around a clause they (or their lawyer) have red-lined. Here's what happens next, from the other side of the table:

• You fight hard on the clause that doesn't matter. A massive fight over the wording of the non-compete, say.
• Then you slowly give way. Each concession builds goodwill, and gives you a reason to ring-fence the commercial terms, which are far more important.
• The process gets long and laborious. The more time the founder invests, the less likely they are to walk away.

Sometimes founders end up signing when they didn't originally want to, purely because they've put so much time into negotiating the wording of one clause that was pretty irrelevant anyway. Meanwhile, the commercial terms end up massively in the other side's favour.

So before you or your lawyer red-line anything, decide what really matters to you, starting with the commercial terms. Negotiate those first. Then deal with the wording. And if you notice you've spent an hour on one clause, ask yourself who that's helping.

Can founders learn to sell?

Yes. Some of the best communicators in business started out as some of the worst.

Warren Buffett has said that until he was about 20, the thought of public speaking made him physically ill. He signed up for a Dale Carnegie public speaking course, then lost his nerve and stopped the cheque. Later he went back and paid the $100 in cash, so he'd have to turn up. He has called it the most important degree he has, and he keeps the certificate on display while his university diplomas aren't (CNBC). Today he's famous for the way he explains his thinking to investors.

Founders are smart, motivated people. They're risk-takers, and they're used to learning new skills. So it's very common for them to start off as terrible salespeople and communicators and end up among the best in the world.

They get there by trial and error, by studying, by hiring people who can help and support them, by taking coaching and courses: by investing time and money in the process.

Why learning to sell the slow way costs founders

The problem with learning that way is that it's slow, and building the next unicorn is about moving fast and breaking things. Every pitch you get wrong while you're learning is an investor, a customer or a hire you don't get back.

So many great founders never bring their dream to life, because they lack skills in an area they never learned and that often doesn't come naturally to them.

The shortcut: someone over your shoulder on every pitch

That's what I built topclosers.club to be. It's someone standing over your shoulder on every single pitch, showing you best practice.

It isn't generic advice. It's specific input, built on personal experience that's directly relevant to founders, including what I learned sitting on the investor's side of the table, watching founders win and lose the room.

Either learn the skills over the medium to long term, which everyone can do, or take a shortcut: a tool that speeds up your learning now, so you can get on with building your unicorn.

Frequently asked questions

Do I need a non-technical co-founder to sell for me?

Not necessarily. Investors want to see that someone on the team can sell, but that someone can be you. Selling is a skill you can learn. If you do bring in a sales co-founder, do it because they bring more than a skill you could have learned yourself, not because you never tried.

Can a technical founder become good at sales?

Yes. Founders are smart, motivated risk-takers who are used to learning new skills. Many start out as terrible salespeople and communicators and go on to become some of the best in the world. The difference is how they learn: by trial and error over years, or with someone showing them best practice on every pitch.

What do investors look for in how a founder pitches?

Beyond the deck, the product and the traction, investors are assessing whether you can sell. Can you explain the problem clearly, keep their attention, answer the question they actually asked and change direction when they push, and negotiate with a clear head? Everything still goes through due diligence, but how you sell shapes how the rest lands.

What should a founder focus on when negotiating a term sheet?

The commercial terms first. Many founders spend hours on the wording of one clause, such as governing law or a non-compete, while the commercial terms end up in the investor's favour. Those clauses can matter, but far less. Decide what really matters to you before you or your lawyer red-line anything, and negotiate that first.

How long does it take a founder to learn to sell?

On your own, by trial and error, it usually takes years. You can cut that down by getting feedback on every pitch: from a coach, from people who have sat on the other side of the table, or from a tool built on that experience.

See it in action: A founder's week with a top closer on call: customers, investors and hires

Read next: The art of negotiation in sales · Selling by listening: the power of shutting up