%20(1).png)
By Randall Kaplan
I once walked into a founder meeting already intending to invest $250,000. I’d read the deck, liked the business, and asked for the introduction. Unless the meeting revealed a serious problem, I wanted to participate.
Just before I walked in, my seven-year-old daughter texted me. She was home with a 103-degree fever, crying and asking me to come home. I told her I’d be back in ninety minutes and went into the meeting anyway.
The next day, the founder told me I wouldn’t receive an allocation. When I asked why, she said my mind seemed elsewhere and I didn’t appear interested.
She was right about my attention. I was interested in the business, but my behavior communicated something else. I describe that experience in Prepare to Shine because it exposed a gap in my preparation that knowing the numbers couldn’t close.
Founders face the same risk from the other side of the table. Our preparation has to include the way we listen and respond when the meeting stops following the script.
Before the meeting, we should understand why this investor may be a fit. Their public investment focus, preferred company stage, and relevant portfolio can help us form an initial view.
When an important criterion is unclear, we can ask about it. That is more useful than assuming an investor’s interest in one company means they will be interested in ours. Preparation should help both sides discover whether there is a reason to continue.
An investor needs to understand what the business does before evaluating its potential. We should be able to explain the customer’s problem, what we provide, and how the business makes or intends to make money in plain language.
A rehearsal with someone unfamiliar with the business can reveal where our explanation breaks down. If that person cannot describe the business back to us, we’ve learned something worth addressing before the meeting. The confusion may be in our language or in a part of the business we haven’t thought through sufficiently.
Every important claim should have something underneath it. When we say customers are enthusiastic, we need to explain what they’ve actually done.
A positive conversation, a product trial, a signed agreement, and a payment tell different stories. The investor should not have to discover those distinctions through repeated questioning.
The same care applies to numbers. We should know the period a growth figure covers, what is included in revenue, and which assumptions drive a projection. The deck, supporting materials, and spoken answers should agree.
That level of familiarity frees our attention. We can discuss what the numbers mean because we’re not using the entire conversation to remember where they came from.
Most founders can identify a part of the business they would rather explain later. Customer acquisition may depend heavily on the founder. Revenue may come from a small number of accounts. Renewal behavior may still be unknown.
Those uncertainties deserve preparation. If several customers have completed trials, for example, we should be clear about how many have become paying customers and what remains to be learned.
We can discuss the next test, the information we expect it to provide, and what we would do if the result disappoints us. That gives the investor a clearer understanding of our judgment as well as the business.
We should also be ready to connect the proposed funding to specific work and milestones. A hiring plan becomes more meaningful when we can explain what those people would accomplish and why the work matters now.
An investor who asks whether customers will renew may be questioning the durability of demand. A question about hiring may reveal concern that the business depends too heavily on the founder. If we rush to deliver a memorized answer, we can miss what the investor is trying to establish.
When the concern is unclear, we can ask: “Which part would be most useful to explore: the renewal evidence so far or what we’re doing to understand the risk?” That gives us a chance to address the actual uncertainty.
Extreme Preparation® includes rehearsing this kind of exchange. A coach or trusted advisor can challenge a claim, interrupt the sequence, or ask for evidence we haven’t brought. We can then see where our understanding is incomplete and where our response becomes defensive.
When we don’t know an answer, an accurate follow-up is more useful than an improvisation that later needs correcting.
The person who met us may need to present the opportunity to partners who weren’t there. A focused follow-up should help that discussion: the corrected number, the requested customer evidence, or the explanation of a risk that remained unresolved.
This is where Extreme Preparation® carries through from research and scenario planning to execution and follow-through. We’ve considered the people, the decision, the difficult questions, and the information that may need to travel beyond the room.
My mistake taught me that interest we don’t communicate can be indistinguishable from indifference. A founder deserves our full attention, and an investor meeting deserves preparation for the human exchange as well as the business case.
My podcast In Search of Excellence explores conversations with entrepreneurs, investors, and other accomplished leaders.
Randall Kaplan is a serial entrepreneur, investor, and executive coach. He’s a co-founder of Akamai Technologies and the founder and CEO of JUMP Investors, which has invested in more than 100 early-to-late-stage companies, including Google, Seagate, and Lyft. For 25 years, he’s coached hundreds of entrepreneurs, business owners, and executives. He created Extreme Preparation® to help people pursue their boldest ambitions, overcome the obstacles standing in their way, and change the course of their careers, businesses, and lives.
He also interviews some of the world’s most successful people, including Mark Cuban, Tony Robbins, Mike Tyson, David Solomon, and David Rubenstein, on his podcast In Search of Excellence, which has reached as high as #3 in Entrepreneurship and #10 in Business on Apple Podcasts.