A sales or fundraising process is a series of “Yes” decisions that the prospect or investor makes over time. If you’ve been running a startup for any time, you understand that the first “Yes” is critical.

It is in the first “Yes” that a prospect or investor gives you a chance.

My hypothesis is that many startups never get to that first “Yes” because they are asking for too much.

They have a Big Ask, that involves too much risk and too much commitment.

But in order to shorten the distance to “Yes,” I’ve seen that founders rarely use what I call the Small Ask.

The Small Ask

✅ The Small Ask involves two things:

1) It thoroughly answers the recipient’s question of “Is this worth it?” and,

2) It is paired with a singular ask that is so low-risk and low commitment that it becomes a no-brainer decision to take the action. ✅

The Small Ask is Low-Risk

✅ “I don’t have much or anything to lose.” ✅

The Small Ask is Low-Commitment

✅ “There are few or no strings attached at all.” ✅

Contrasting the Big Ask vs. The Small Ask

Humans in general are always being asked for things that are in short supply - namely, time and money.

Founders are always asking customer prospects first for their time with the hope that they will eventually get money in the form of revenue.

Founders are always asking investors like myself first for their time with the hope that they will eventually get money in the form of investment.

These Asks are are agnostic to context - it can be the ask for a customer to convert from a free product to a paid product, it could an ask at one the last line of an email, etc.

But on that journey of asking, asks typically sound like what I’ll call the Big Ask, or the Typical Ask. Let me give some examples.

Email Context

I went through my email over the last two weeks and picked out the "ask" lines of each email. The action the sender is trying to get me to take. It’s a mixture of sales reach outs and founder reach outs. Here is compilation of the asks that I have received:

The common denominator with the Typical Ask, and these above, is that they all involve high risk and high commitment.

It’s high risk - if I say that I’m interested, I don’t know what I’m going to get next. I’m most likely going to get hounded by a salesperson, among other things. At a minimum, I’m saying yes to a series of many more decisions after this one.

But it’s also high commitment - nearly all of these Asks ask for a commitment of time. They are either forcing me to think about my response, Or, they are requesting a commitment of a 15 or 30 minute call with a person that I do not know.

High risk and high commitment.

But an Ask can also pertain to a software product.

Product Context

This past week, I was talking with a founder that has a B2C software play. The founder started talking about their customer funnel. Currently, the founder is running a freemium business model with a specific number of days on a free trial.

The founder noted that their current challenge wasn’t as much about getting customers into the funnel, but rather the free trial to paid customer conversion. The founder noted that their percentage of free to paid was actually lower than the industry average for products like theirs.

That comment was a signal to me - something might be off with the Ask. So I probed more and asked about how the free to paid conversion ask is made.

The founder told me that they had a specified number of days on the free trial. I asked, “Why that number of days on the trial?” The founder asked, “Do you think it’s too short?” I said, “No, I think it might be too long!”

As we were talking, there were a number of variables in this free to paid conversion at play:

• The number of days in the trial

• Where in the user journey the paywall is placed (at the beginning before the trial, at the end after the trial, etc.)

• The language of the offer sounds like when the ask

• Among others

I saw it like this - users had signed up for this product on their own will. They were using the product on their own will. So my fundamental conviction was but there was something in the Ask that was holding these free customers from converting to paid.

As we were talking, we uncovered that the startup seemed to have a Big Ask - they were asking the customer to convert to paid but there appeared to be quite of bit of risk and uncertainty in making the decision, not to mention a high level of commitment for the user.

In real time, this founder and I started brainstorming about different possibilities at iterations. My job wasn’t to tell the founder what was optimal, as the founder needed to run experiments on those variables to determine what was optimal.

But my aim in that moment was to break the mental frame of the Ask - that the secret to solving the startup’s free to paid conversion dilemma likely rested in the best combination of the variables to create a Small Ask.

The prospect needed to see if it was worth it, and they needed to take an action that represented a low risk and a low commitment decision.

Shrink the Ask

In the way that I think about Small Ask, it’s actually based in psychology.

In the book Switch: How to Change Things When Change is Hard, authors Chip and Dan Heath, write about how to change things when change is hard. One of my favorite quotes from the book is this insightful statement, "What looks like resistance is often a lack of clarity."

Put another way, if there is resistance (i.e., a prospect or investor not taking action on a Typical Ask), it might not be because they don't know.

They may not be taking action because they don't see. They don’t have enough clarity to know if they want to take action.

The founder is asking a knowledge question, "Do you know if want it?” and assumes the value is clear. 

Yet, the prospect or investor is asking a question that involves sight and clarity, "Is this worth it?"

They don’t know if they want it because they don’t see that it’s worth it.

The founders job is to thoroughly answer the question of “Is this worth it?” and pair that with a singular ask that is so low-risk and low commitment that it becomes a no-brainer decision for the customer.

If they do not, the results will never change. What looks like resistance is a lack of clarity. Because, as Chip and Dan Heath point out, "The most familiar path is always the status quo.”

The Importance of Discovering for Oneself

Now, there is one watch-out I’ve seen with this.

It’s that I discern that a lot of founders automatically want to own the responsibility themselves to guide the prospect to help them see if it’s worth it.

I’ve been a founder myself, and I remember that I enjoyed guiding prospects to the “A ha” moment in the product. It felt emotionally good.

So, founders ask the customer prospect to book a demo to walk them through the value. Or, founders ask the investor for 30 minutes of time before the investor knows if the conversation justifies the potential fit.

Let me ask a legit question - Do you really need a demo for them to have the clarity of “Is it worth it?” Do you really need to be as high touch as you are to help prospects see “Is it worth it?”

But can something else serve that purpose without you being “in the room”?

Here is what I have seen in observing many, many startups:

Often times, the best thing that your prospect or investor can do is discover by themself if it is worth it, without the founder or startup being “in the room” as it were.

The startup founder’s job is to intentionally shape the path so that the prospect or investor can discover themselves if it’s worth it with the least amount of effort possible, in a low-risk and low-commitment way.

The Small Ask doesn’t ask for much commitment - you might not ask for their time at all, at least not initially.

It doesn’t ask for a lot of risk.

The Small Ask just shows up and helps the prospect or investor answer the question that they fundamentally are seeking to answer, “Is this worth it?”

Then, putting in a singular action for them to take that is low risk and low commitment.

In the Small Ask, maybe the best thing you can do is not try to enter the room too soon, as it were.

What the Small Ask Could Look Like

The Small Ask helps the prospect discover “if this is worth it” by themselves, and is paired with a singular ask that is low-risk and low-commitment.

The beauty of this is there is no end to the creativity of what this could look like.

The types of products, the go-to-market motions, the pricing, the end customer, among others, are all variables.

In Fundraising

Going back to the visual above of all of the Asks on the email, notice all of the asks above where founders asked me as an investor if I wanted to see their pitch deck.

The Big Ask like this makes me decide on a variety of decisions, “Is this company a fit,” “How does this startup compare to this other startup that I’m aware of,” “Why are the terms so high relative to the traction?” And then, the Typical Ask asks me to get past all of that and then take the action that the founder requests in their email.

I’m just going to say it. That’s a Big Ask.

Instead, founders may think about doing Founder and CEO, Ryan Wheeler of our portfolio company, Cylerity, did upon an email intro to me.

Back in July 2024, I got introduced to Ryan from one of his employees, Aaryush. In his intro email accepting the intro, Ryan also sent a longer narrative that was broken down into a few headings with details underneath. It gave a brief overview of the company in bullet point form:

• Problem:

• Solution:

• Headline Numbers: (featuring product traction, customer traction, and fundraise traction with specifics from specific investors)

• Economic model:

At the end, Ryan then threw out some times that he was available to meet via Zoom.

What I founder interesting is that there was no deck to review. What I saw in the email was what I got. Ryan’s contained the information necessary for me to have a conversation.

I didn’t have to respond to the email to ask for a deck, like all of these asks above.

I didn’t even have to click a link, which could even be a good approach in some cases.

His email had this “no frills” feeling to it. I liked it a lot.

The Small Ask limits the surface area of the recipient’s questions but answers the question, “Is this worth it?” Then it makes a low-risk and low-commitment ask.

In Tech Products

Showing is often highly superior to telling.

A low-hanging fruit way is to deploy visual assets.

One of the Tundra Angels’ portfolio companies is Octane Coffee, a robotic automated coffee and drink drive-thru. It’s an amazing technology that customers get on the Octane Coffee app and place a drink order. The GPS tracks the location on the way to the kiosk and perfectly times the drink making so that when the customer arrives and scans the QR code, the cabinet rotates and the drink is ready to grab and go.

Octane Coffee is a geographically-dependent product. A customer cannot experience the product in true form unless the customers goes through the actual flow. But wisely, Octane Coffee has a product video that lays out the entire experience. So that prospects can see “if it’s worth it” before they go through the steps.

Closing Thoughts

A sales or fundraising process is a series of “Yes” decisions that the prospect or investor makes over time.

Because it is in the first “Yes” that a prospect or investor gives you a chance.

My hypothesis is that many startups never get to that first “Yes” because they are asking for too much.

Either the recipient is resistant because of a lack of clarity - they do not know if it’s worth it. Or, the ask is too large and involves too much risk or too much commitment.

So let me ask you:

What is the #1 most critical ask that is fundamental to your startup winning that you make right now?

How can you shrink that #1 ask in two ways - so that the recipient can discover themselves if it’s worth it in the easiest way possible. And, how can you pair that with a singular ask where they don’t have anything to lose and there are little to no strings attached?

Startup founders optimize for their product, their optimize for their KPIs, they optimize for their GTM strategy.

But the Power of the Small ask acknowledges that the hidden truth is that humans are always being asked for things that are in short supply - namely, time and money.

So don’t run off and optimize something else…

I’d ask you to make your #1 Ask, a Small Ask.

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