I learned Oodles from JIFF’s Startup Showcase
February 24, 2020
If you’re new to D-TECH.FUND, we’re just a group of folks hosting startup showcases for diverse tech founders in NYC, the second largest startup hub in the United States.

We’ve hosted 3 startup showcases since November 2019, including JIFF, and you can find our complete schedule at d-tech.fund

After each startup showcase I publish an article on JustMyNewYork about what I learned.

Here’s what I took away from JIFF’s startup showcase.

#1 How to deliver a killer presentation (in lights).

Alex was the first to arrive on the day of his startup showcase, with his photographer (and brilliant + charming partner).

I still wasn’t ready for the showcase yet.

In fact, I was ending a work call, and just shy of putting the finishing touches on setting up for JIFF’s startup showcase when they buzzed our apartment.

As an upgrade to our typical setup, I had a projector I’d been waiting patiently to use for just this moment, but I couldn’t figure out how to connect all of my devices to it so that Alex and I could scroll through our phones to show his app on the main projector screen for our guests’ enjoyment.

I thought I had it covered (I didn’t) with a multi-purpose adapter that looked like a small floppy disk, but I forgot how I accomplished this last time, and multi-tasking wasn’t working for me.

As I googled how to connect our iPhones to my computer, and then to the projector, Alex reached into his backpack and pulled out his boondoggle adapter.

He then proceeded to connect his Apple products into one seamless connection to our projector, in a JIFF.

This was our first time using the projector-projector screen combination, and generally our first time with projection technology for startup showcase, at all.

In a room full of captivating art pieces from @RobertNewmaniii’s collection, additional light from JIFF’s sleek interface on our white projector screen imminently peaked our audiences’ curiosity about what was to follow.

This projector-based pitch enhanced our overall startup showcase experience in more ways than one, and I can’t imagine going back to the way things were before JIFF’s showcase.

For example, say you need to search the Internet to make a strategic point or to address a question during our signature Q&A session in real time?

For example, like comparing your UX design to “one of the people we call competitors” and what that juxtaposition looks like side-by-side.

You can flash any problem that you’re solving on a gigantic screen, in real time, with lights and art everywhere in a room full of folks who truly embrace a specifically-curated environment built on mutual vulnerability.

Alex enhanced our core values in ways our guests openly appreciated and communicated to me.

Here’s the deal, pretend you’re a novel guest attending one of our startup founder showcases.

Now imagine, as a guest, you’re ascending myriad stairs inside of a Harlem brownstone and into a new diverse tech studio environment.

Your friend calls this meetup an “app launch party”.

When you’re asked what you expect to experience tonight, you return a curious blank stare.

That’s a typical experience, however on February 15th...

JIFF delivered.


Lesson #2 how to design a sleek user interface.

JIFF’s eye-catching innerface is practically fluorescent.

If you’re like me, you like the idea of having artistic depictions of sensational emotions at your fingertips.

JIFF actually did it.

Ironically, this particular innovation came from JIFF’s earliest users, it’s test groups, of which they are plentiful.

In fact, I’ve noticed this specific character trait in other successful early stage founders: the art of meticulously testing their products before launching (as Alex has).

It’s particularly important to get this right in well established industries, because those markets are brutal teachers and expensive too.

JIFF leveraged its survey respondents to help build a specific design feature-picture captions-making my earlier description of JIFF’s user interface even possible.

Listen to Alex tell his story for yourself....

Also, Alex said something profound to me in my office the week following his startup showcase. 

After JIFF’s redesign and new aesthetic, Alex told me that this kind of attention to user experience and visual appeal was necessary “when you’re trying to do something new”.

In fact, JIFF’s first product design was buried, never to see the light of day.

“I wouldn’t show that to anybody and I told [him that].”

From JIFF, I learned that you get that which you demand from service providers.

To me, that translated into a killer product for JIFF’s users.

Lesson #3 how to pitch, in the age of short attention spans.

Alex delivered by far the best pitch we’ve heard so far at a D-TECH.FUND event.

In a way it was our first real pitch.

Esusu’s showcase was a celebration for its Series A round

The Blast App was long overdue showcase for a one-of-a-kind social messaging app

Alex came with a slightly different plan for his startup founder showcase.

He sought to educate our room full of sophisticated people about a well known application in an unknown future, for a commonly-used product. 

Confidence means a lot in a room like that, whether it's a dozen and a half people, or six hundred in attendance.

If you’ve attended at least one startup showcase, you already know the best part of our nights, the highlight and something folks remember most: the Q&A.

Alex got questions like, “What’s the ROI?”

He didn’t answer that question, at least not directly.

But here’s why.

It’s not the type of question a founder could (or should) answer, but Alex did.

In an inviting, yet reasonable way.

Again, imagine you were attending JIFF’s startup founder showcase for a second.

You’re in the room, and all of a sudden you raise your hand, to ask the first question.

Plus you’re on the front row.

Again, a common situation our guests find themselves in during our events.

Then a guest who’s a VC, behind you, asks if JIFF would consider going international, specifically to Europe.

That’s a VC question if I’ve ever heard one.

Although, that’s what you would want from our startup founder showcases.

These types of engaging questions allow founders to do what they do best: set the vision.

I told Alex before his launch, “you’re the show” and “the people are here to see you”.

In response, he put on a masterpiece.

As the same surrounded him.

Now, think about being a guest who rolls in right before we start our startup founder showcase?

This actually happened to JIFF. 

Two guests showed up minutes before our startup founder showcase and still got looped into the night seamlessly.

If JIFF’s goal was to confirm that a pre-seed round was possible, today, they did that easily and again, only with a dozen and half people in the room.

NYC’s startup scene is growing.

Lesson #4 how to win a room not thinking about investing.

How’d Alex win over the room at our startup showcase? 


He was the first person to show up and last person to leave.

Our first New York native too. 

Watch the the full recap, including Alex’s genuine smile, native New Yorker appeal and straight to the point personality.

JIFF wins.

Over and over again. 

During his pitch, Alex was in our head, literally.

Since the day we met, Alex has read nearly every article out there on pitch decks and presentations.

So I never doubted that he would deliver.

He was clairvoyant during his startup founder showcase.

Anticipating questions before they were asked, and putting on a timeless display and show for our audience.

It’s well-established that the guests attending our startup founder showcases are well educated and open to asking the hard questions.

We like it that way.

Lesson #5 how to be inclusive in a polarizing world. 

Another first.

Seeing a pattern here?

JIFF was also  the first startup to invite a live guest on stage during their showcase to engage with their product in real time. 

A complete, and total experience for everyone present, including me. 

We open our startup founder showcases with an extemporaneous speech from a random guest in the audience on the night of the showcase.

They typically don’t know that I plan on asking them to speak in front of the entire crowd that night, ahead of time.

This time it was Alex’s partner who delivered a heartfelt answer to the question of “why we’re here tonight”.

Because JIFF could be a game changer or in the words of Alex, “I know it is” we understood that you would either love the idea, or hate it.

Alex had a large task ahead of them. 

In an industry mired in red tape and political skepticism, Alex convinced a room full of sophisticated folks that now was the time to support JIFF.

Specifically, Alex’s concise pitch helped open the door for questions that reinforced his strategic vision.

Considering joining the local NYC startup scene?

Follow us at d-tech.fund

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