June 6, 2025

From Vintage Shops to Coffee Ventures: A Journey of Creativity and Community (with Kerry Simon)

From Vintage Shops to Coffee Ventures: A Journey of Creativity and Community (with Kerry Simon)

This podcast episode serves as a compelling showcase of insights derived from the experiences of a seasoned bootstrapped entrepreneur (Kerry Simon). Central to the discussion is the premise that success in entrepreneurship often hinges upon the fortuitous alignment of factors such as timing, location, and community engagement. Kerry recounts their multifaceted journey, which encompasses the establishment of vintage clothing shops and a coffee business, emphasizing the importance of social interaction and organic marketing strategies in fostering business growth. Furthermore, he candidly reflects on the challenges faced, including the stark contrast in outcomes when replicating a successful model in a different market. Ultimately, we aim to provide our listeners with actionable takeaways that can be readily implemented in their own entrepreneurial endeavors.

Takeaways:

  • In the realm of entrepreneurship, one must recognize that success often hinges on a confluence of opportunity, timing, and sheer luck, as illustrated by my personal experiences.
  • Establishing a strong social presence and engaging actively with potential customers is pivotal for bootstrapped ventures to flourish and achieve recognition.
  • Kerry's initial foray into business was characterized by fortunate circumstances, such as low overhead costs and immediate customer access, which significantly contributed to my early success.
  • Investing in a marketing budget is imperative for sustaining visibility and engagement, as organic reach on social media platforms has significantly diminished over time.

Links referenced in this episode:


00:00 - Untitled

00:44 - Untitled

00:49 - Introduction to Showcase Episodes

02:08 - Launching New Ventures: From Vintage Clothing to Coffee

03:44 - The Impact of Timing on Success

05:43 - Strategies for Business Success

07:14 - Building a Community for Success

07:56 - Understanding Marketing Budgets

Sarah St John

Welcome to the Frugalpreneur podcast. I am your host Sarah St. John.This episode is what I refer to as a showcase episode where I feature a bootstrapped entrepreneur and they briefly share their tips, tricks, tactics, techniques and tools that help them bootstrap their business and the successes and failures along the way.My hope is that each of these showcase episodes will provide at least one valuable takeaway that you can implement with right away in your own bootstrap business journey. Now onto the episode.

Kerry Simon

I've always had the entrepreneurial spirit.I started my first business at 11, managed a team of other kids to mow lawns, and even though we weren't really good at it, we had a lot of fun and we learned a lot.In my twenties I ventured into the world of vintage clothing and I eventually opened two vintage clothing shops in Texas and in some circumstances led me to create Proletariat, which was a streetwear, graffiti supply and skate shop near Harvard University in Cambridge, Massachusetts. And that really sparked my love for blending culture and creativity and business together.After proletariat, I spent 10 years in the corporate world, Rose the chief Marketing officer of an international retail chain with over 200 locations.But even as I was at the top of that game, I was finding myself spending my few spare moments I had with my best friend starting our coffee company called Nowhere Coffee Club.What was really driven me through all these ventures is just a deep desire to create things that bring people joy, that spark community, and hopefully offer something better for the world. So when it came to opening my first vintage clothing shop, I had a few things going for me.The rent in the location that I was looking at was very cheap at the time, few hundred bucks a month, and it was directly across the street from a major college campus, Texas A and M University. So I was fortunate enough to have too many customers, low rent, which gave me a lot of leeway to screw things up.I opened that business on a credit card, which is very risky. I think had a $3,000 mat max on that.But I had also been selling clothing on ebay and knew that I had an opportunity to make the money I needed to make to cover my bills just on ebay alone. So the store didn't exactly have to take off right from the beginning, even though somehow I was lucky and it did.As far as my new business with my best friend, Nowhere Coffee Club, he and I agreed to put in $5,000 each as a start. That quickly ballooned to more like $10,000 each. But we are in a position now, later in our life, that that is a doable amount of money for us.So looking back at that vintage clothing business, I was wildly successful out of the gate, too successful.There's no reason why someone who had never owned a business, didn't have a business plan, didn't have financing, should have brought home $70,000 in his first year at 23 years old. So many, many, many times, success is really right place, right time, luck. I mean, Facebook's an example of that as well with Mark Zuckerberg. Right.Just right place, right time, big community luck.What's interesting is I took that exact same retail concept that was killing it in two stores in Texas and I moved to Cambridge, Massachusetts, Boston area, and cloned the experience. And within the first year I was at negative $50,000. And I actually had experience this time around. Right.It was actually a business owner who had done that exact business.So you can never plan too much, you can never get enough insights, you can never ask enough people about your business because once you're in it, you gotta go hard.

Sarah St John

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Kerry Simon

What I can tell you is when you look at those 10 years I worked in the corporate environment, the entire reason that I had to do that is cause I was paying off debts from the failed business. In my opinion, that's my advice for you personally.If you're gonna be bootstrapping a business on a budget, my Advice for you is to get really social. You need to be out there. You need to be among the people who are going to be your customers.You need to be among the people who are your peers in your industry. If you have a retail location, you definitely need to have a good Google My business profile or Google Business Profile, it's called now.You need to be on social media. You need to be constantly having conversations with people.You need to constantly remind people what you do and why you're different and why you're the best. A lot of that can be done free or very cheaply. And then also find like minded people to collaborate with.Every single person who's walking around has a circle, a circle of customers, a circle of friends, a circle of families. And you can do constant trades with them of let me promote you, you promote me.But I can tell you that you end up bringing a larger group on board, you are going to be more successful quickly. The other thing I'd say is you need to be very realistic with your time of life. A young person is just actually going to know a lot more people.So when I started my business in college, I knew hundreds of people who were excited for me and who were excited to know the cool new thing.And now that I'm in my 40s, I'm having to pay for that traffic because my circle has shrunk as I've in some ways moved around the country, I'm just not quite as consolidated as I was in my 20s. That would be it. Stay social, meet people, show your expertise, support other people, promote other people and you'll have a better shot.So we are currently building Nowhere Coffee Club on a very small budget with a lot of organic marketing.I can tell you the things that have worked best for us is using SEO to find the queries that people ask for and having blog pages and having that well written content on your site. We do get some organic traffic from that.The other thing I would say is while our social media channel at Nowhere Coffee Club on Instagram, we make fun videos. We're obviously collaborating with people a lot.What I'm finding there though is the algorithm is restricting your views because at the end of the day, Facebook wants to make money. So don't think that you can build everything organically anymore.You have to have a budget for marketing and you have to be able to boost posts, you have to be able to run meta ads because you'd be putting out the most solid content in the world. It's going to restrict how many people see your content. So think of a marketing budget as part of your actual expenses. You have to buy inventory.Sometimes you have to have a location. You have to have a marketing budget. People do not need to go to you.They're always looking for the new thing and you have to stay top of mind out there for them.

Sarah St John

I hope you enjoyed that episode and were able to take away a valuable nugget of information that you can implement right away in your own business. If you feel your story would be valuable for the listeners of this show, please visit Frugal Show Guests.