Pitching online: 7 Data-Driven Tips for Having Conversations with Investors
By: Gleb Maltsev
Tags: Pitching, Storytelling, Startup, Entrepreneurship, Fundraising

During the past weeks, I’ve done webinars with over 150 founders ranging from Oman to Poland. Just over a month ago I’d be preparing them for high-stakes presentations in front of packed conference halls. Today, the limelight got replaced by desk lamps. The coveted headset stage mics and pics gave way to pixelated video feeds and your laptop’s standard stereo set-up. The same set-up that lets everyone know when your cat is hungry unless muted.

Meetings, networking events, conferences and conversations moved to Zoom, Crowdcast, Hopin, Slido, and Slack. Some of the tools aren’t new and have been around for almost a decade. At the same time, there are over 2 million new active monthly Zoom users that joined during the past few months. That’s more than the company added in all of 2019.

We’re experiencing a global experiment in remote work. This experiment is changing the way we speak, have conversations and pitch. Here are a few takeaways to help folks prepare for this new normal.

1. Trim the filler

Up to 23% of a pitch ends up being noise. When you look at the average you end up with every 29th word being an ‘uh’ or an ‘uhm’, a ‘so’, a ‘th-th-this’ or one repeated for no reason. This insight comes from an analysis of a 165,000-word data set of pitch transcripts that my team and I have been collecting.

Those pitches start conversations between the founders and the jury of investors. They’re called Q&As and make out a separate data set of almost as many words as the pitches. Many of those conversations are painful to listen to and more so to transcribe. Yet, it’s those few minutes that can make or break a pitch.

The fluency heuristic is a term from psychology for a mental shortcut we use to decide whether to listen to it or not. The concept is key to understanding a core challenge with remote presentations and pitches right now.

2. Write down a script

An online pitch can feel much like throwing words into a bottomless well and not hearing anything come back. As a result, we end up filling the void until our message drowns in noise.

To help your audience get your message you’d need to write it down first. Pitching or speaking — unless you’ve been doing it for some time — is not improv. It doesn’t mean that you’d need to go all ‘Wolf of Wall Street’ with a polished sales script devoid of all filler words. Keep a conversational pace of 130–140 words per minute, sprinkle it with pauses and at least a few ‘human moments’ to go with it.

Try to go analog; screens tend to distract and prevent us from writing the way we speak. I’d suggest to write down a draft, read it out loud, edit and then test it on a colleague or your Maine Coon before going live. Ask them for feedback to make sure you sound authentic.

3. Record a video

Live pitches are hard. A momentary lag can disrupt the flow of a sentence or a technical glitch with Zoom can disable the scheduled Facebook live stream.

A founder can record a short back-up video or screencast walk-through of their deck to prepare for those moments. Tools like Loom, Adobe Spark, Veed.io, Monosnap or Quicktime can get you started. For the more advanced I’d suggest investing in a Shure mic, one or two cameras, and Adobe Premiere Pro. Consider setting up a reverb and an echo-proof room with proper lighting. In both cases, you’d need to plan out time for video editing, and rendering. This becomes even more relevant if you’re caught up in the madness of an online hackathon with a deadline looming.

There are also those who aren’t ready to turn their homes into film studios just yet. They might want to design their pitch decks for smaller screens and buy a headset mic.

4. Brace yourself for traction questions

Polishing your video and delivery can only get you so far. Investors will still ask you a similar series of questions. Those questions are somewhat predictable. It helps having a catalog of over 1,400 of them in a spreadsheet.

They will revolve around your go-to-market strategy, product, business model, customers, and competitors. The key differences would be that until the ‘fog of war’ clears investors will remain super picky and risk-averse. They’ll want to know about your plans for the next 18–24 months, which may or may not involve a pivot. Be ready to show your traction. Many founders would be negotiating from a much weaker position than was the case just a few months ago. This depends on their runway and industry.

The key thing here is that your goal as a founder is to focus on opportunity and the long-term vision of your firm.

5. Schedule your calls in the morning

CEOs pitching investors remotely might seem like a new concept to some. It’s not. Before the days of crowdfunding or peer-to-peer lending, leaders of publicly held U.S. firms would have quarterly earnings calls.

Back in 2012, three researchers published their analysis of 26,585 calls between the period of January 2001 and June 2007. What follows is a direct quote from their paper’s abstract.

“The evidence indicates that the tone of conference call discussions deteriorates markedly over the course of the trading day, with both analysts’ and executives’ moods becoming more negative as the day wears on.” — Chen, Jing and Demers, Elizabeth A. and Lev, Baruch Itamar

6. Warm up your voice, and smile

Studies show that smiling affects how we speak and how others can ‘hear us’ do it. It has to do with our facial muscles and how they affect the pitch of our voice. A tense jaw or shoulders can lead to tightness and restrict your vocal range. Massaging your cheeks, stretching, chewing and humming can help expand it in the morning. Saying ‘wow’ five times with gradual increases in excitement can help wake up your lips and your neighbors. Drink water. Take it easy on the coffee, alcohol, and cigars — the stuff tightens your vocal cords. For more vocal warm-ups I’d recommend ordering a copy of “This is a Voice” by Jeremy Fisher and Gillyanne Kayes.

The key takeaway from this is that speakers can go a long way with an occasional smile in the morning to remind us that this time too shall pass.

7. Make sense of your narrative

An analysis of hundreds of post-mortems by CB Insights listed the common reasons why startups fail. They include but are not limited to failing to find a product-market fit, burning through the cash, and not having the right team. Others are about competition, pricing and cost issues.

The takeaway here is that a founder can look at the game of fundraising like a chessboard. Instead of trying to outwit his counterpart, a founder can avoid the most common mistakes in how he plays the game.

With pitch content, it would mean thinking through the common risks and removing the reasons for the investors to say no. This includes non-committal phrases. Classic phrases like “If you get a lead investor, we’re in” or “We want to see traction before we invest”. More recent ones would sound like “We’d like to come back to this once the fog clears”.

Once the potential red flags are dealt with, the rest becomes about knowing how to tell a story in front of a camera. The kind of story that shows your team solving a real problem for your customers. That’s it.

A note about the future

“Venture capital is truly a long-term game.”— Scott Kupor, Managing Partner at Andreessen Horowitz

I’ve first read the quote in “Secrets of Sand Hill Road” back in 2019. Later I heard it paraphrased by several VCs investing in this region. One did so right after I finished training folks for this year’s Fifty Founders Battle at TechChill. Now it’s used with words like ‘dry powder’, ‘open for business’, ‘fog of war’, ‘capital deployment’, ‘board’, and ‘profitability’.

In this game of funds founders still need to ask whether their vision is ambitious enough. This has to get done before scheduling back-to-back meetings, virtual or otherwise. Ambitious still means aiming to be the +$100 million exit in the investor’s portfolio in the next 7 to 10 years. Yet this long-term view is now coupled with a focus on cash and short-term survival.

It’s during this time that there’s still one thing investors hate more than a write-off. It’s failing to deploy capital and knowing that they missed out on getting in early on an opportunity of a decade. Their scorecard depends on it.

After all, some of the tales we read about are of founders that built companies in a time of great uncertainty. Think Airbnb, Dropbox, Twilio, and that ride-hailing company. The one that became the foundation for countless high-concept pitches.

It’s up to founders to get investors to put their capital where their Medium posts are.