🏗 Digital Minimalism and Startups: An Interview with Jack Greco

I interviewed Jack Greco, Techstars Executive Director and ACV Auctions Co-Founder (11 min read)

Jul 24, 2020

Homescreens is a weekly publication about how we interact with our most intimate possession, our phones. Each week I interview interesting people across industries and we reflect on the apps they use, how they’re organized, and their philosophy on notifications and mindfulness.

Perhaps there is no one more embedded in Western New York's startup ecosystem than Jack Greco. The Co-Founder of ACV Auctions, the first billion-dollar unicorn company to emerge from Buffalo, NY; Jack now serves as an Executive Director for the seed accelerator Techstars. Now, you'll find Jack spending his days mentoring founders, advising budding startups, and helping to create a culture that supports and nurtures would-be entrepreneurs.

Every Wednesday at 10 am, the latest edition of Buffalo Bridge hits inboxes across Western New York— an introspective preamble written by Jack starts it off. It's peppered with interesting articles, job listings, and community events. It finishes with a link to Open Office Time, a site that at no-cost allows you to book a meeting with community leaders from across industries— Jack's calendar is filled with these micro-meetings, sometimes upwards of fifteen hours a week.

When I emailed Jack for this interview, he responded, saying that I'd get to see how much of a minimalist he was— he wasn't joking. His home screen has a total of eight apps: four along the top and four in the dock. Not a folder in sight. The way Jack uses common, stock apps like Messages and Calendar is incredibly unique and refreshing.

Here's our interview, edited for length and clarity.

Jack, how are things?

Things are good, I'm an angel investor now, I started a not-for-profit— a fund to fund investments. Every year I'll donate to any number of non-profits, and I should be able to continue for the next twenty-five years if I do this right. I did that, I gave my mom money to retire, and the rest I'm using to invest. I'm an angel investor in about four-dozen companies in upstate New York now.

Very cool, on Linkedin I’ve followed a lot of these companies you're now involved with like SomaDetect, Forsake—

Yup! I’ll basically go into anything that I think the founder has a chance, because I think everyone gets a chance, and that they will do something good with the money. I basically take what I make from my Techstars salary and donate half of it, and I live off the other half.

So how do you want to do this? I think it's a neat idea. It's a niche thing; it's a unique mirror into people's lives. I'm looking at this one for Mike (last week's interview), and I don't know how this dude has all this crap on his screen [laughs]

I think that's a pretty normal home screen! Now, you only have four apps on the top, you weren’t kidding about the minimalism. Do you just keep your most-used apps on the home screen, and everything else on page two?

Yeah, so my second page is all the crap I can't delete, right? It's got the calculator, the notes thing, the settings thing. The only special one I have here is the Red Cross blood donor app because I donate blood a lot, that's really the only thing I have there by choice. Also, I don't use email on my phone, and I don’t go on the internet on my phone.

Wait, you said you don't go on the internet on your phone?

I hardly do, you'll notice Safari is not a button here. On the bottom, I have my camera because I'm taking pictures of my kid all the time. I have Maps because I need to know how far away I am from places. I actually try to use my phone as a phone. Then I have my phone button and the calendar—which I live out of. Though I set up almost zero meetings through my calendar, I use Calendly for everything—it saves me at least five hours a week. I don't do any email on my phone; I have no email setup— zero. I've taken a lot of time to get people to realize that.

I'll use Slack occasionally, basically because I have to. As you know, the Western New York Startup Community is on Slack, Techstars is on Slack, and I'm in all these random channels. What I like about Slack is, it's user-sourced content. I could go on Google and type entrepreneurialism, and see what a robot tells me, but I actually do my searching by the Slack channels and the people I listen to.

Really? That's super interesting!

Yeah! So I'm in a Slack channel that you're in. If you post something there, I have a much higher likelihood— I would rather it be human-sourced content than algorithm-based rankings. I get information in two ways, Slack and I get a paper copy of the Buffalo News that I read every single day. I read it in the morning, and I read the same paper at night—I read it twice, and then I do the crossword before I go to bed.

Very cool. You put a lot of thought into how you use your phone and how it's laid out.

Yeah, my ideal phone is like my ideal remote control. If I want to control my TV, I want to have one big red button that I press, and it turns on what I want for as long as I want and then will turn the TV off automatically. You'll notice on my home screen I have the Calendar there, but I have Calendly piped in the back end that automatically loads all my events. I have forty-two calendars running. I use calendars almost like messages. I have a calendar for Sabres season tickets with three other guys, if we want to communicate on it, I don't even text them, I put it in the calendar, and they automatically get a notification.

You've inspired me to use Calendly.

Here hang on, let me screen share with you.

Jack shares his desktop screen. I see Calendly open above a monochrome taskbar.

Is that…a skin to make Windows look like XP?

No, it is Windows XP. I refuse to upgrade my computer, it's like a 2008, but I beefed up the guts, so it runs.

Jack proceeds to give me a demo of Calendly— how he uses it, sets it up for consulting, and how it integrates with his calendar. It’s great, I’m sold.

If you're going to take something away from this, it's that my home screen is as simple as it is because I follow a couple of rules, like I use my phone as a phone and my computer as a computer. There are people that are attached to their devices, and I think this is because they give them infinite use. I probably look at my phone about an hour a day, and it's mostly for text, but to be honest, I don't even like looking at my phone to text. I voice-to-text everything; I hate typing. That's why my texts look very conversational because when you talk, it comes out differently than when you type. Also, I'll click on Messages, and I never try and have them—

Do you try to basically have zero red badges?

I use Messages like a to-do list, outside of a couple of group messages. If you and I are having a conversation and I have a thread open, as soon as we conclude what we're talking about, I delete the thread. I had reached out to a bunch of guys: one in Boston, one in DC, one in San Francisco, and one in New England—four guys that knew the startup ecosystem in their cities— on the same day before COVID. That Sunday, everything shut down, so I keep them because there's still something for me to do there.

Wow, I've never heard of this practice before, that's honestly wildly interesting.

I text on it, I Slack on it, and the third button on mine, called Bridge, is actually really, really cool.

Yeah, I don't recognize that app, and it looks like it's through Test Flight?

Yup, I met the guy on a phone call, I had a forty-five-minute call with him at the end and I was like, "can I please invest in this?" And he said, "Yeah, I'm looking for angel investors!" It’s a way to keep track of the connections you make. As you can see, I've made 293 intros in the last month-and-a-half to 242 people, and I've gotten feedback about 217.

This is very cool, reminds me of a grass-roots version of LinkedIn with intros instead of random people adding me that I don't know.

Exactly! So texting I do a lot, Slack because I have to, and Bridge because I want to. And, I keep Pandora on here because I just like music. I have some really weird channels that are weird mixes.

What's the weirdest one?

I have one that's C.W. McCall, mixed with The Minibosses which is like a grunge band that plays Nintendo music, mixed with Genesis, mixed with Son House— on random, and I actually think it's mixed with John Williams who's the one that writes "Name that famous movie's" score. And I think I have Bach and Pachelbel mixed in there too, it's super eclectic— so Pandora will play four songs in a particular genre then flip-flop. Pandora actually has some really cool things that Spotify doesn't. I like discovery and deep-cuts.

I don't see too many people using Pandora anymore. It's all Apple Music and Spotify.

Why? One thing you won't initially gather from my home screen is that I HATE recurring expenses. I have zero debt in my entire life. I own my house, and I own my cars, I have no credit card debt, nothing. I don't live in a really big house, and my 2005 Grand Cherokee is in the shop because the transmission fell out. The reason I don't have 50,000 apps is because I don't want to pay for 50,000 apps.

Everything is a subscription model now.

Every year with Pandora, I make the decision if I want to spend $45 on it, and I do, and it's paid upfront. When you're an entrepreneur, you can't afford to have a high burn. Some of these guys just go and buy fancy cars and nice houses, but it makes you full and fat, and I always want to be lean and hungry. You need that nimbleness to be able to jump into things.

Well, you've kept that pirate mindset.

I only got this phone (iPhone 6S) because I was at ACV and had to have it. I had a flip phone until 2015 when we launched. I think there's a future world where there are no apps, or people don't live by apps. Everything that I use my phone for is a utility, and I think that should be baked in without me having to push a button.

Have you ever looked into the Lightphone? It’s a super minimal phone that uses an E-ink display.

Oh, that’s cool! I’m going to have to look into this.

I think this whole idea of digital mindfulness is getting popular and gaining steam. People are being more mindful of what apps they're using and how much time they’re spending on social media.

I put timers on my things. I'll get a notification if I've been texting for more than 30 minutes a day, and it comes back up every 5 minutes. I do have Safari in one of the utility categories in case of emergency, but one of my own hacks is that I use Maps for phone numbers. I'll go into Maps, click on the link and find the phone number.

And finally, who do we have on your background?

That is my grandmother and my son, two people at the time I was responsible for taking care of— and the two reasons I’m in Buffalo. My family is the center of my world and there is no app important enough to cover their faces. Every time I look at my phone, I want to be reminded that the experience should be brief, so I can get back to what matters.

Endnote

Thanks for reading my interview with Jack. Find him on LinkedIn here, and learn more about Western New York’s Startup Community here.

📱 App and Media Recap

📆 Calendly
🌁 Bridge

Homescreens