Talking Squarely

There isn’t one playbook for running a business and the decisions business owners face are rarely straightforward. Every other week, we’ll bring together independent business owners to have frank discussions and share their perspectives on some of the most pressing issues impacting their lives—from the changing rules of commerce to work-life balance.

Ep. 01

Talking Squarely About What’s Next

The COVID-19 pandemic has reshaped the global economy, and in many ways small businesses have been hardest hit. Four business owners from across the country discuss how their respective regions are approaching life after coronavirus, how they’re grappling with the potential return to a new normal, and their experiences navigating it all—from unclear local and federal guidelines to the ability to quickly adapt. Featuring Kallie and Lindsay Wesley, sisters and co-owners of Juxtapose in Tampa, FL; Carrie Morey, founder of Callie’s Little Hot Biscuit in Charleston, SC; and Marc Magliozzi, owner of Dozzino in Hoboken, NJ.


Ep. 02

Talking Squarely About Doing Good

In times of crisis, sellers are often motivated to help in whatever way they can. But, how can businesses contribute in times of financial struggle? We sit down with three business owners to discuss the creative ways they are lending a helping hand to those in need and building up their communities. Featuring Sam Shih, owner of 9Tailors in Boston, MA; Yassin Terou, owner of Yassin’s Falafel House in Knoxville, TN; and Lauren Crabbe, owner and CEO of Andytown Coffee in San Francisco, CA.


Ep. 03

Talking Squarely About Financial Survival

From downsizing staff to navigating relief programs, businesses are being forced to make difficult financial decisions — more than usual. We ask three businesses how they are dealing with financial uncertainty in a time when simply paying the rent and utility bills seems daunting. Featuring Lauren Stovall of Hot Sam’s in Detroit, MI; Evan Kidera, owner of Senor Sisig in San Francisco, CA; and Brittany Sarhage, owner of Rudy’s Flower Truck in St. Louis, MO.


Ep. 04

Talking Squarely About Black Businesses in America with Killer Mike

In this special-edition episode of Talking Squarely, we talk with rapper and entrepreneur Michael Render, more commonly known as Killer Mike, about how to encourage Black economic inclusion and entrepreneurship during a time of increased racial tension in the United States. And we discuss what it means to be a community leader, and his own journey of entrepreneurship.


Ep. 05

Talking Squarely About Black Businesses in America, Part 2

In part two of this episode, we explore the day-to-day experiences of being a Black business owner in America. From getting started to fostering a community, we’ll discuss economic inclusion and entrepreneurship with Black business owners from across the United States. Featuring Shamar Cotton of Everett & Jones BBQ in Oakland, CA; Lauren Stovall, Director of Marketing at Hot Sam’s Detroit in Detroit, MI; and Yolanda Owens, owner of iwi fresh in Atlanta, GA.


Ep. 06

Talking Squarely About Marketing Safely

As new health data and guidelines are released, reopening plans across the United States are ever-changing. And, for business owners looking to encourage customers to return to brick-and-mortar locations, prioritizing the health and safety of their employees and community is both a tactical and marketing challenge. We sit down with three business owners to discuss how they’re ensuring their community is not only informed about the types of precautions they’re implementing, but also ultimately feels comfortable revisiting their stores. Featuring Omar Kinnebrew, owner of Bespokuture in Atlanta, GA; Nicholas Pidek, owner of Foster Coffee Co. in Owosso, MI; and Dr. Jonathan Kaplan, owner of Pacific Heights Plastic Surgery in San Francisco, CA.


Ep. 07

Talking Squarely About Seasonal Business Change

Seasonality plays an important role in many businesses’ annual plans, as it often helps predict the ebb and flow of sales. But with the current state of the world, certain guaranteed seasonal boosts are less likely to come to fruition. We sit down with three business owners to discuss how they’re preparing for these unexpected changes. Featuring Suzanna Cameron, owner of Stems Brooklyn in Brooklyn, NY; Kim Moistner-Bartlett, Kona Ice Franchise Owner and Chief Learning Officer; and Beau Coan, Chief Operations Officer of Papa Noel Christmas Trees in Texas.


Ep. 08

Talking Squarely About The New Realities of Selling Online

For many businesses, selling online is no longer a nice-to-have, it’s a need-to-have. Instead of measuring success in foot traffic, businesses are thinking about clicks and online orders for the first time, which comes with its own challenges, many of them unanticipated or not previously considered. We three business owners to discuss the reality of creating a successful online arm of their business when their previous focus was running and growing their brick and mortar locations. Featuring Chef Leilani Baugh, owner of Roux and Vine in Oakland, CA; CJ Barone, owner of Empire Tea & Coffee in Newport, RI; and David Velasco, owner of The Mellow in San Francisco, CA.


Ep. 09

Talking Squarely About Supply and Demand

COVID-19 has upended global trade. As the global supply chain moved in fits and spurts and infrastructure was rethought to accommodate just-in-time delivery, so too was consumer demand changing as consumers everyday habits dramatically changed. Locally, everything from farms to food processing plants have been affected by shutdowns, impacting how small businesses can restock their shelves. And regulations across the country have changed even what customers expect to see stocked on their shelves. In this episode, we speak with two businesses that have seen drastic shifts in their supply and demand. Featuring Ian VanDam of Civil Alchemy in St. Louis, MO and Karla Mancio, Head Roaster, Red Bay Coffee in Oakland, CA.


Ep. 10

Talking Squarely About Trying Something New

As the world changes around us, businesses of all sizes are reimagining what and how they sell to customers. From the “new normal” to the “next normal,” business owners are leaning into a startup mentality — rethinking their pre-existing models of success and seeking out new or unforeseen opportunities. In this episode, we speak with two business owners who have evolved their businesses to meet the emerging needs of the time, and how this has shifted their thinking about long-term business planning and their vision for the future. Featuring Angel Gregorio, owner of The Spice Suite in Washington, D.C. and Bailey Ryan, owner of PlantBar in Virginia and North Carolina.


Ep. 11

Talking Squarely About Work-Life Balance

For many small business owners, there is a balancing act between running their shops, having a family, and, now, dealing with a global crisis. In this episode, we talk with three business owners about how they balance both the professional and personal, what that balance actually looks like, and how COVID-19 has changed their approach. Featuring Cheryl Tisland of Burst of Butterflies in Chandler, AZ; Samir Idnani of NaanStop in Atlanta, GA; and Danielle Mullen of Semicolon Bookstore in Chicago, IL.

Ep. 12

Talking Squarely About Season One

Throughout Season One of Talking Squarely, we’ve talked to business owners across America about the most pressing issues impacting their lives and livelihoods. In this episode, we’re taking a look back and talking about why Square decided to create the show, what we learned about business ownership, and some of the moments that stood out during the first season. Featuring host Nelson Murray in conversation with producers of Talking Squarely, Cindy Lewis, Square’s Head of Editorial, and Mallory Russell, Square’s Head of Content Marketing.