š Trading in the Suit for Blue Jeans: Leaving Corporate America and Founding aĀ Startup
I interviewed Greg Bailey, Angel Investor, and President and CPO at Denim Social (13 min read)
Homescreens is a weekly newsletter where I interview founders and creators about what's on their phone. Each week I feature a new guest in tech and we reflect on their favorite apps, productivity hacks, and unique quirks. If youāre reading this and are not subscribed yet, consider joining this growing community.

Greg is an entrepreneur, startup advisor, angel investor, and former corporate executive. Heās a seasoned vet in leading digital communication, social media, and mobile experiences at the intersection of marketing and technology. Greg has founded or co-founded five businesses, so he knows a thing-or-two about building a startup.
Gregās phone reflects this. Youāll find product management and people management apps alongside audiobooks and reading material. The dock is limited to just three communication apps. Iāll let him tell his story in his own words.
What follows is our interview, edited for length and clarity.
Greg, thanks again for joining. Walk me through your entrepreneurial journey and what led you to where you are now.
You bet! So Iām a serial entrepreneur, either founded or co-founded five or six businesses, depending upon how you look at it. Back in 2003-2004 I started my first business and closed that down with the great recession of 2008. Ran that for about five years then went back into corporate America and had some executive roles ā I was a 2X chief marketing officer for major financial services companies. In 2015 I left the corporate world, and I told my family that I traded in my suit jacket for blue jeans and denim, and then named my company Denim.
So I was the founder of Denim, a tech software company, that I created out of Des Moines. We grew that to multiple customers and built our product in the social media and mobile advertising space. [We had] a web-based application used specifically for financial services and insurance companies. Four months ago, in April of 2020, we merged with another software company ā kind of the idea that 2+2 doesnāt equal 4, but 2+2 = 7 or maybe 8 ā a lot more value out of two companies coming together. So today I serve as president and chief product officer for Denim Social, which is the name of the new combined company.
In addition, back in 2015 some co-founders and myself created a micro-venture fund, or I just call it a seed-stage angel investment fund, to make investments specifically in technology companies focused on disrupting the insurance industry. Nowadays thatās referred to commonly as a kind of buzz-word, āInsurTechā, which is like a first cousin of FinTech.
The last thing Iāll mention is Iām an advisor to an app-based business called Given. Given is a web and mobile application focused on connecting nonprofits that have needs, with people and businesses who are willing to give. So think of an app that makes it extremely easy and removes the friction for individuals and businesses to find nonprofits, and those who have specific needs for giving, to help them fill those needs.

Congrats on the success, and congrats on the merger of Denim and Gremlin. You already answered my first question about the name, Denim, and the thought behind it. Itās catchy.
Iāll say this, there are a few axioms about brand names that are really important, and one of them is: thereās only one way to spell the word and one way to say the word. It doesnāt matter where you are in the world, Denim is Denim, it has no other pronunciation or spelling. The second this is: is it a word that can be redefined? A common example of this would be the word apple. Today, if I say apple, your first thought is likely not a fruit. Your first thought is likely an iPhone or a Mac. So choosing a word like denim, we felt that was a word we could redefine over time what it means, especially for our customers. The third thing is: is there a domain name that is either available or available at a reasonable price? So our company lives at DenimSocial.com.

Great answer. Diving into your phone, itās very organized. You have folders at the top for travel, work, social, listening, and books, I see Asana, Slack, and Superhuman of course. Give me an idea of how you use your phone in the day-to-day?
Yeah, so I think it depends on the day of the week and the time of the day. So if it's Monday through Friday, I'm pretty well-on for business. It's a lot of email, calendar, apps like Fellow and Asana, which helped me run the business and keep track of things and even like Calendly for scheduling purposes.
If it's outside of business hours, like early in the morning or in the evening, or the weekend itās social media. If you looked at my time spent, itās the typical Twitter, Facebook, LinkedIn ā those three would rank high.
The rest of them like podcasts, audiobooks, and reading apps like the Harvard Business Review, even Pelotonāthose would be a little less time, but still ones that I actively use every week.
Tell me about Fellow, thatās one app I donāt recognize.
Itās a terrific company, in fact itās a startup out of, I want to say Toronto, and they are growing very, very quickly. They got their start by being both a web-based app and a mobile app that helps managers manage their agendas, meeting agendas, and conversations with employees during one-on-one conversations. They have these templates that a manager can use to organize the conversation that theyāre going to have with their employee.
In a way, the product has evolved, and it is a very focused version of Google Docs, where the manager and the employee share the document. Both parties can type in their notes, talking points, and action items ā so now the action items have become my to-do list, and itās become a central source for all of my meeting notes.

It's become a great place to have all of our meeting notes in one central place we all have access to. Our action items are a great way to follow up to make sure we're completing the things we committed to. Also, this ability to have documents that are everything from OKRs and KPIs documented, to things like values and mission and vision [statements] for the business. So itās almost like a common place that the employees have access to certain documents. So a very focused, easy way to keep track of meetings and just various types of notes and action items.
I feel these collaborative productivity apps are having a heyday right now. You look at Coda, Airtable, of course Notion ā theyāre all doing something a little different, but itās very interesting.
Interesting you point out Coda, we use it in our product team. Itās primarily used today in our product area for company documentation around how weāre building and scoping products and prioritizing our product roadmap.
In the past, probably a couple of years ago, our team started using Notion. A few people like Notion a lot, but the majority of our team could not figure out how to use Notion any differently than we were already using G Suite, and so it just became a simple replacement for Google Docs. I told the team ā look, if we canāt figure out how to use it any differently than Google Docs, then weāre not going to use it. So we no longer use Notion.
Thatās fair. I feel like thatās one of Notionās pitfalls, they donāt make it very obvious. Itās very powerful and very fast, but they donāt make it obvious as to how it can be implemented and how teams can use it.
To your point, you have to think about āhow do I want to organize my work?ā Notion gives all that flexibility. Whereas Fellow says, āthis is how you do itā.
Right, a jack of all trades but master of none.
Yeah, kind of that way.
You mentioned more of your āfunā apps earlier like Kindle and Podcasts, what are you reading, and what are you listening to?
So Iāve got two books, and oneās called Powerful: Building a Culture of Freedom and Responsibility, by Patty McCord. Patty used to be Reed Hastings head of HR at Netflix, and I donāt know if youāve ever heard of the Netflix Culture Deck, itās a slide deck thatās probably more than 100 slides. If you were a new hire at Netflix, they felt it was so important about communicating the culture and expectations at Netflix, this is the deck that all employees would receive from the leaders at Netflix.

For fun? I don't know if I've got any fun books here at the moment ā actually, this one: Leadership: In Turbulent Times by Doris Kearns Goodwin. I'm a big American history buff. And so you know, this is Abraham Lincoln on the cover and this particular book takes kind of an interesting perspective and point of view on American presidents. It takes Abe Lincoln, Theodore Roosevelt, Franklin D, Roosevelt, Lyndon B. Johnson, and compares and contrasts their leadership styles as presidents.
So my go-to podcasts: I love Masters of Scale by Reid Hoffman, founder of LinkedIn. One of my all-time favorite podcasts is Business Wars by Wondery. Thatās been an ongoing series, and one of my favorite seasons is PayPal versus eBay. They document the story about the early days of both PayPal and eBay as competitors and who won that business war, so thatās a great podcast. I also enjoy Inside Intercom just from a business perspective and talking about product management and how to scale your SaaS company, thatās been an enjoyable podcast to listen to from time-to-time.
Typically podcasts for me are not entertainment, theyāre more to learn something or to hear other business peopleās points of view on a particular topic.
And sometimes audiobooks are easier than actually reading a book; this particular book Iāve listened to on Audible, but Iāve also read the book twice. Itās a book called Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days. Itās about the exercise around how they go through the sprint planning and sprint execution process around ideation and product development.
Thatās one Iāll definitely have to check out, I just saw my Audible membership renewed today. How do you make a decision between what youāre going to read and what you want to listen to?
Itās funny you ask that itās a great question. Most of the books that I have as a physical book I also have on Audible. I realize itās paying twice the amount or its duplicative, I get that, but most books I donāt read cover to cover as a physical book. Iāll either start with the audio version, then at some point Iāll read a bit of the physical book, and then Iāll finish it on Audible. I find I get bored otherwise. It helps me comprehend, sometimes itās quiet and I can really dig in to actually reading a physical book, but a lot of times there is a commotion going around and you slip headphones on and I comprehend it better. So it just depends.
Very interesting. I see youāre a fellow Peloton user. Are you a digital subscriber? Or, do you have the Tread or Bike?
I have been using it for digital subscription. So whether it's a walk or a jog, my wife's also used it for yoga, and different things like that. I've also used it for some meditation. I'm very, very close to taking the leap and getting the bike ā I'm probably going to do it this week, so it's that close. It's imminent.

[Itās been a few weeks since this interview, Iāll have to check in to see if Greg got his Peloton]
We got ours right before the Pandemic, it was perfect timing. Itās great. Another app that we have in common is Superhuman. How long have you been a user?
Iām going to say itās been close to a year now that Iāve been a Superhuman user. Itās been fantasticāprior to Superhuman, Iāve always been one thatās used my inbox as a file storage mechanism. This aspirational objective that all of my colleagues were talking about of āinbox zeroā was always some lala-land for me that I could never wrap my head around. Now, Superhuman has taught me that thereās a certain thought pattern and workflow that youāre to follow as you go through email, right? For me, the biggest benefit is the idea of putting keyboard shortcuts into my muscle memory; understanding that āh' means schedule to come back to later, and āg iā is go to inbox, and āenterā is reply-all. Just knowing that, and sitting down and powering through email nowadays is a lot different behavior than picking up the Magic Mouse and moving it around the computer screen. I never appreciated before Superhuman how disruptive and inefficient taking my hand off of the keyboard, then moving it over to the mouse, then moving the cursor around the screen to lick something is. So now Iāve gotten to drink the Superhuman Kool-Aid. How have you found it?
Almost exactly the same reasoning. It's really opened me up to using keyboard shortcuts in other apps as well, like Slack, and places I never used them before.
It makes me think about what other types of areas in tech and apps that are just outdated and need a different perspective. I think we could almost point to Superhuman and kind of call out now that they were one of the first to rethink the workflow management of an age-old tech like email. And since then, now Basecamp has come out with their Hey product. Hey email is another twist on email, so itās interesting how certain types of companies are popping up to rethink something like email. Itās interesting to watch.
Are there any apps that we havenāt talked about yet that youād like to bring up?
I think thereās one app on my home screen thatās noteworthy for an interesting way, though not the way youād think. Letās take it to the native apps on iOS, starting with the Phone app. Itās my business phone, my personal phone, it is my phone, right? Now, the amount of telemarketers and other business salespeople [calling] is going up and up, and the effectiveness of reaching me through the phone is just non-existent. I donāt want to answer the phone, right? Unless I know who it is, like my mom or something like that.

The other one that I wanted to point out, also native to iOS, is the Camera. Itās fascinating to me that nowadays, this iPhone, more than probably anything else, to me is a camera and a communication device. Email, Slack, text messaging, you saw those across the bottom, thatās my mode of communication. Then the camera in the upper left to take photosā I love taking photos with the iPhone.
This has been great, very informative and a lot of fun. Thanks for your time Greg, weāll talk again soon!
Alright, take care!
Endnote
Thanks for reading my interview with Greg. Find him on LinkedIn, Twitter @gbaileycom, and check out his newsletter Rivet, where he talks about building a startup.
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š± App and Media Recap
šĀ GivenĀ ā The Given platform connects people and organizations in need with people who are willing to give.
š»Ā AsanaĀ ā Asana is the work manager for teams. From the small stuff to the big picture, Asana organizes work so teams are clear what to do, why it matters, and how to get it done.
š»Ā FellowĀ ā Give and get real-time feedback on meetings, projects, and performance through the app or in Slack.
šĀ CalendlyĀ ā Calendly helps you schedule meetings without the back-and-forth emails
š°Ā Harvard Business ReviewĀ ā HBR now provides you with the ability to access the power of the print magazine, alongside our most important explainer videos, and award-winning podcasts on your mobile device.
š²Ā PelotonĀ ā Transform your fitness routine at home or outside with thousands of on-demand classes taught by our 30+ world-class instructors-guaranteed to get you energized.
š»Ā CodaĀ ā Coda docs start simple like other docs ā and grow and evolve into powerful tools.
š»Ā NotionĀ ā One tool for your whole team. Write, plan, and get organized.
š§SuperhumanĀ ā The fastest email experience ever made.
š§Ā Hey emailĀ ā HEYās fresh approach transforms email into something you want to use, not something youāre forced to deal with.
š Books:Ā Powerful: Building a Culture of Freedom and Responsibility, by Patty McCord,Ā Leadership: In Turbulent Times,Ā Sprint: How to Solve Big Problems and Test New Ideas in Just Five Days
š Podcasts:Ā Masters of Scale,Ā Business Wars,Ā Inside Intercom
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