Entrepreneurs Heart Hartford — Kate Callahan

ewalsh • October 23, 2015

This blog series, posted in partnership between HYPE and reSET, offers a platform to showcase the commitment that Hartford entrepreneurs have for their work and this city. It examines how entrepreneurs have chosen their work, and provides examples of the ways in which they are having an impact in Hartford. In this edition, we interviewed Kate Callahan, an award-winning singer/songwriter and college essay coach.

1. Please tell us a bit about yourself, and why you do most of your own booking and management.

I’ve always been inclined to work for myself. I get great satisfaction from succeeding in practical pursuits. The nuts and bolts side of my life as a musician & entrepreneur doesn’t come naturally or easily though, I love improvising with my voice and losing track of time in my rehearsal space more than anything, but filing my taxes and booking 6 months of shows challenges and grounds me in a really good way.

2. Why did you decide to be based in Hartford?

I got my start in New York City in 2000. After a year gigging, waiting tables, and recording my first record, I knew my soul was in a crisis. I was lonely, losing money, and starved for nature. I was 23 at the time and my dad said, “Why don’t you come home?” It made sense to me. I was looking at Northampton, MA and Woodstock, NY but I couldn’t bring myself to sign a lease. So I came back. I’ve been living in Hartford ever since. It’s a good home base. The stakes aren’t as high so I’m not as focused on pure survival. I have more energy to give great concerts because of that.

3. How do you think your work as a musical artist impacts the community and vice versa?

Reviewers and promoters in this area have called my music “Emersonian,” “Angelic,” and “Graceful.” I appreciate that. I live on Main Street in Downtown Hartford. When the windows are open, my soundtrack is traffic, horns, and sirens. There are so many sirens, emergencies, desperation. I write music in my apartment, so I’m often creating songs that are aching to be beautiful amidst all these sounds, and that ache reminds me of the pain city neighborhoods go though when they’re facing emergency and aching to be beautiful in new ways. So the city is reflected in what I write lately.

4. What words of wisdom would you give to aspiring entrepreneurs who may be hesitant to take the plunge into entrepreneurship?

I’d tell them it’s essential to align themselves with some kind of accelerator or incubator program…maybe even before they take the plunge. This way aspiring entrepreneurs can gather a holistic and realistic picture of what the first 5 years will look like. Entrepreneurial communities, like reSET, where I cowork from, make self-employment a lot less isolating. A lot of questions start-ups face, get answered in entrepreneurial communities.

5. What’s it like being an artist/entrepreneur in Hartford? What are the benefits, but also what are the difficulties and challenges?

Working as a singer-songwriter over the past 15 years, I’ve had many successful launches in Hartford. Each time I release an album I produce a concert to debut the music. It’s been thrilling to have packed venues for each of these album releases. The Hartford Courant, former Hartford Advocate, West Hartford News, and West Hartford LIFE among others are consistently supportive in reviewing and promoting my albums. Consequently this helps me launch into bigger cities, where I’ve received national press coverage.

In terms of challenges, I would like to see more draw for live music. There are parts of the US where a steady diet of live music quenches people’s thirst for creativity and energy. I’d love to see the Greater Hartford community more hungry for new sounds and live music outlets.

6. What’s your vision for your business and personal development over the next five years?

I’ve focused so heavily on giving concerts for over a decade that I’d like to break into licensing and getting my songs placed in film, TV, and commercials. I’m exploring new sounds (electric guitar, cello, singing bowls) and vocal improvisation right now which I’d like to see develop into more experimentation in my music.

When she’s not performing or working out of the reSET Business Factory, you can find Kate at:

https://twitter.com/katecalsings

https://www.facebook.com/KateCalSings

https://www.youtube.com/user/tunetraveler

https://instagram.com/tunetraveler

http://www.artofthecollegeessay.com

By awalsh July 9, 2026
Showcase Awards Over $18,000 in Grants and Prizes
By awalsh June 26, 2026
Nine Entrepreneurs Celebrate Graduation from Spring Cohort and Share Over $15,000 in Prizes and Grant Support
June 25, 2026
Launching a New Statewide Partnership to Connect Aspiring and Growing Food Businesses with Structured Programming, Education & Resources
Sarahblecher
June 23, 2026
Marketing Strategist and Connecticut Small Business Mentor Succeeds Sarah Bodley
By awalsh June 4, 2026
Eight Businesses Will Compete for Over $15,000 in Prizes and Grant Support at CT State Community College–Gateway
May 14, 2026
Reset announces its new logo
May 14, 2026
A Day Full of Honest Connection for Entrepreneurs
By SBodley May 7, 2026
This Spring we asked our community to weigh in on their biggest challenges, interests, and opportunities related to impact-driven and sustainable business. We were proud to partner with CT Sustainable Business Council on this effort. Select findings were shared at Beyond Business As Usual 2026: Scaling Resilient Entrepreneurship, and we aim to continue taking action on the things that rose to the top. Click through the arrows to see the key findings.
By awalsh April 23, 2026
 Summit Brings Together State Leaders, Policymakers, and Entrepreneurs During National Small Business Week
April 2, 2026
reSET to Host Beyond Business As Usual 2026: Scaling Resilient Entrepreneurship One-Day Summit Brings Together Connecticut Entrepreneurs, Policymakers, and Innovation Leaders During National Small Business Week