How to Grow your Startup: Reverse Engineer Moments

9 min readSep 11, 2020

By Brian Scordato, Founder of Tacklebox Accelerator and the Idea to Startup Podcast

Your startup (and lots of other very important things in your life) will depend on moments. These moments seem, and often are, serendipitous. You get a job because you bump into someone at a wedding, you meet your spouse in line at Whole Foods, your startup gets funded because the kid of an investor you’re pitching loves your product.

These moments drive everything. Yet we leave them to chance.

This post is about how to orchestrate the moments that change behavior. How to identify and understand all the inputs that go into a meaningful moment, and how to reverse-engineer them. Creating these moments takes empathy, creativity, and a good bit of chutzpah. Shifting your thinking on moments can be transformational.

It also might not be what you’re looking for on a Friday. And I don’t necessarily blame you. In that case, here’s Grab a drink and sail away with some sultry 80s vibes.

For the rest of us, let’s dig in.

How to actually raise funding

Founders want to raise money. Investors want to invest in hot startups. Ipso facto, lots of founders want to make their startups look like hot startups.

There are two ways to do this

1) Literally be a hot startup — Have a level of traction that makes it obvious you’re in the top 0.1% of all deals. This probably isn’t happening for you. If it is, toss on and get taken away by the sultry 80s vibes because you’re in great shape.

2) Give the impression that you’re about to be a hot startup — make it seem like everything is lined up for your company to explode and for investors to snatch up all the space in the round.

None of this is revolutionary yet. Here’s the see-saw for fundraising:

Ideally, you’re this founder:

But you’re almost certainly this founder:

The second founder, the one that represents 99% of startups, feels like they’re in the chicken-and-egg scenario of needing investment so they can get to the type of traction they would need to get investment. I’ve spoken with hundreds of these founders over the years and they’re (understandably) frustrated. They end up doing all the things perfectly reasonable articles like this tell them to do:

  • Start early to get commitments and leverage those commitments in future conversations
  • Get press for social proof
  • Lower their “target raise” so they can say they’re “oversubscribed” and create fomo
  • Send updates to investors every few weeks to try to show up and to the right

None of this is bad advice. But it’s ignoring that people live in moments. I woke up this morning with a horrible stomach ache. My birthday was last week and I’ve been pigging out on cake and a bunch of cupcakes Brendan sent me (thank you sir). So, this morning when I woke up I got pissed off and decided to commit to trying intermittent fasting for a week. Moments drive action.

Your job, as someone looking to change behavior, is to dig in on the moment.

Start with what the person you’re trying to influence wants. You need to know a ton about them and their process. We know that investors want a hot deal. So what’s that practically look like?

That’s create a scenario where an investor would almost HAVE to invest. And let’s say, like most founders, you don’t really know any investors. Here’s how an ideal cold intro → invest might look.

  • You, the founders of the startup Eastminster (it’s Westminster but for mutts and doodles — way less snooty), are intro’d to Investor X by someone they trust. The trusted person says they know and believe in you, that you’ve opened up a funding round today, and here are two bullet points that show action.
  • Investor X reads the email and decides to answer it later.
  • Two hours later, that same trusted person pings them again — “hey, just wanted to follow-up as I heard from the Eastminster founders and XYZ Impressive Person is in. Apparently they invested today after seeing the deck. Not sure how long the round will be open.”
  • Investor X is now intrigued — they respond asking for an intro.
  • Eastminster replies immediately — “We loved your investment in X and Y, and heard your podcast with Z. Here’s our deck, we’ve also got time to chat tomorrow or Friday. And actually, if you’re around, our call just cancelled and we’re free right now.”
  • Investor says “let’s talk now.”
  • Call goes great. It’s 20 minutes.
  • Investor goes into partner meeting and brings it up — “pretty crazy day — heard up this company, they opened up funding today, XYZ Impressive Person is in, they sounded great on the phone. Things are moving — we’d likely need to move fast. Should we bring them in Friday to meet us all?”

And now you’re a Hot Deal™️

The key here is understanding what script will lead to the decision you want. A version of the script above is one a Tacklebox alum used recently. It’s brilliant. Most fundraising startups puddle along having meetings, trying desperately to force investors to make a decision, bleeding cash and time. But investors are always incentivized to wait until there’s real urgency. This Tacklebox alum created it.

Once you know the script, work backwards. Here’s how you create the above scenario:

  • Get something really compelling (aside from your startup, which needs to be compelling or this all doesn’t matter) and bank it. Influential person committed to $10k, company to pilot with, etc.
  • Pick a date for the fundraising bonanza kickoff: Day Z
  • Find 50 connections (“Connectors”) on LinkedIn who will give you trusted intros, and search for the two best possible connections for each.
  • Email connectors 10 days prior Day Z asking if they’ll intro
  • Day Z: Send an email in the morning BCC’ing connectors — it’s go time — give them the two bullets, ask for the intros, say you’re hoping to close the round by the end of the week
  • Three Hours Into Day Z: Email with the compelling thing from above. “X investor is in — feel free to ping your contacts, as this may speed up the round.”
  • This increases the value of the intro and makes it 10x more likely the person ACTUALLY DOES make the intro they said they’d make. Now, you’re interesting.
  • Follow-up to BCC’d email if / when interesting things happen.

Social Proof + Momentum + Fomo = Investment.

Do you need a company worth investing in? Yeah, of course. But I’ve seen way too many companies that were worthy of investment flounder around without creating moments until they failed.

Investors can stay irrational longer than you can stay solvent.


The fundraise example is topical because lots of people on this list have, are, or will try to do it. But moments really shine for customer acquisition.

When I was interviewing customers for Find Your Lobster — the mobile dating app I built that looked a lot like Hinge or Tinder but preceded each by about a year (in my Dad’s words, that plus $2.75 will get you a ride on the subway) — I was searching for a specific moment.

In 2011, most people assumed that the only people using dating apps were either ugly or 35+. Those aren’t my words — those are the words of friends, customer interviews, and countless VCs I pitched. VCs tended to put it in more gentle terms, saying some version of “we don’t think it’s likely that desirable people under 30 will create a dating profile” — but the point stood. Dating apps were a last resort, and no one is chomping at the bit to jump into a dating pool full of people with no other options.

But a lot of my customer interviews told a different story.

People in their late 20s and early 30s in New York City were frustrated. It was tough meeting people, and the old ways — standing at a bar, hoping you liked someone you worked with — weren’t cutting it. When I asked the right questions, I could get a lot of people to admit that they’d poked around on Ok Cupid — always Ok Cupid — and had even considered creating a profile.

I’d push further. What would it take for them to actually create a profile? That’s when people — smart, funny, good looking, desirable people — broke. They already had.

This is the holy grail for an entrepreneur — behavior change. These people lived in a world where dating apps were unimaginable, until they weren’t.

My job was to deconstruct that moment.

For the people who’d joined Ok Cupid, the stories were all nearly identical.

Their roommate or best friend or cousin had been the one they’d go out with, double date with, go to parties with. Then, that person got a significant other. They didn’t want to do all the things they’d done alone, so they found themselves at home — alone — constantly.

Eventually, they met a friend somewhere who was in a new relationship. How’d they meet? The friend leaned in close — “actually, we…. met on Ok Cupid. Don’t tell my mom!”

The next time that person was home alone watching Netflix at 10pm on a Friday night they said, sometimes audibly, “screw it.” By 10:15 they had a profile. By the following weekend, they were on a date.

Reverse Engineering the Script

The script was becoming clear.

Single and frustrated. “Wingman/woman” gets a significant other. Social proof from a friend in a happy relationship who met on Ok Cupid. Next Saturday night alone. That’s the moment.

My job was then to facilitate that moment and swap Ok Cupid for Find Your Lobster. What I needed to create were:

  • A few moments where the customer heard about Find Your Lobster
  • A moment where they met a couple who’d met on Find Your Lobster
  • One last nudge, on a Saturday night while they were home alone, to join

The first and third bullet points were relatively easy. The second was much tougher.

To hit the first, we sponsored happy hours, leveraged (MUCH cheaper) social media ads, were out in rec sports leagues, etc. The third bullet point was a targeted Facebook ad, between the hours of 8pm and midnight on Friday and Saturday, that said something like “Your wingman is in a relationship. Going out alone stinks. It’s your time — meet someone great on Find Your Lobster. A double date is better than whatever’s on Netflix.”

The second bullet is much tougher. How do we get couples that’d met on Find Your Lobster to talk about how they met?

We first broke down where people normally talk about how relationships started — birthday parties was a top one, as it’s often the first place you meet a sig o. We knew couple’s birthdays from the app, so we sent them a drink coupon for their birthday. They’d then be far more likely to be around friends and tell that story. Planting goodwill right before the moment we’d need could work.

What to do with this

Break down your customers behavior to understand what type of moment will change behavior. Write a script for that customer. Figure out how you can make the script happen.

Don’t leave the moments to chance. You’re worth more than that.

And if this overwhelmed you….

Holler at if you want to talk this through!

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And apply to Tacklebox if you want some help — Cohort 25 starts October 28th (all virtual). Founders who apply and are accepted in the next two weeks will have access to a 4-week pre-req workshop leading up to the cohort.




We help founders with full-time jobs validate their startup before they quit. The posts are tactics we use.