Bourbon and Business Podcast
Two friends interview entrepreneurs about their origin stories and business philosophies, always starting with a bourbon tasting.
A casual interview podcast where the worlds of American whiskey and American entrepreneurship meet. Hosts Dakota and Tyler talk with founders—often of regional, non-tech businesses—about their journeys. The bourbon tasting that opens every show sets a relaxed, conversational tone that feels more like a friendly chat than a formal interview.
“The mandatory bourbon tasting segment is the show's most unique feature, creating a distinct ritual and a relaxed atmosphere. The focus on tangible, often local, businesses (pizza shops, barrel makers) and their founders provides a grounded counterpoint to more tech-focused business podcasts.”
Who hosts this show
Bourbon and Business is hosted by Dakota Tate and Tyler Wiltshire, two Mississippi-based friends with backgrounds in finance and insurance. Their mission is to interview successful business people to understand how they think and to show that there is no single formula for success. Each episode begins with the hosts tasting and rating a bourbon before diving into a long-form conversation with their guest.
Credentials & credits
- Dakota Tate: BBA in Business Administration and MBA from Mississippi College.
- Dakota Tate: Certified Trust and Fiduciary Advisor (CTFA) with experience as a Financial Advisor and Trust Officer.
- Tyler Wiltshire: Agent for Insurance Protection Specialists (IPS).
- Tyler Wiltshire: Board of Directors for the Rankin County Chamber of Commerce.
- Tyler Wiltshire: State board member for the National Association of Insurance and Financial Advisors.
- Tyler Wiltshire: Winner of the Top 40 under 40 award for Rankin County.
What kind of podcast
- Country
- United States
- Region
- usa
When new episodes drop
- 01Episode 171 - Gray Welch - don't aim to people pleaseJun 25, 2026 · 29 min
- 02Episode 170 - Daniel Nicholson - strike when the iron is hotJun 18, 2026 · 31 min
- 03Episode 169 - Duncan Welch - know your numbersJun 12, 2026 · 29 min
- 04Episode 168 - Elle Ingalls - rewrite the storyJun 5, 2026 · 44 min
- 05Episode 167 - Elliott Godwin - like ironmanMay 28, 2026 · 30 min
- 06Episode 166 - Luke Kujacznski - noise vs signalMay 21, 2026 · 33 min
- 07Episode 165 - Dylan Crouch - belief is powerfulMay 14, 2026 · 31 min
- 08Episode 164 - Louis James - let him cookMay 7, 2026 · 28 min
Notable episodes
- 01Episode 169 - Duncan Welch - know your numbers
The guest, a fractional CFO, gives highly practical and preventative financial advice for new business owners, like immediately separating finances and hiring a bookkeeper.
- 02Episode 170 - Daniel Nicholson - strike when the iron is hot
Features a frank discussion on the 'unspoken' reality of entrepreneurship and its heavy impact on family life, a recurring theme of the show.
- 03Episode 171 - Gray Welch - don't aim to people please
A classic example of the show's format, telling the story of a founder who left the corporate world and built a local food brand through consistency and authentic social media.
What you'll be asked on this show
The hosts, Tyler and Dakota, favor a friendly, narrative-driven interview style. They almost always open by asking the guest for their complete backstory, starting with where they're from and leading into their business's founding. They are active listeners, building their follow-up questions directly from the guest's previous statements, allowing the conversation to unfold organically. A recurring theme is exploring the personal sacrifice of entrepreneurship, with questions about the impact on family and work-life balance. They create a supportive atmosphere, allowing guests to speak for long, uninterrupted stretches without aggressive pushback.
This is a two-host interview show. Every episode begins with Dakota and Tyler introducing, tasting, and rating a bourbon or other whiskey. This is followed by a long-form, single-guest interview that flows from the guest's personal history into their business expertise.
Questions the host keeps coming back to
11 cataloguedIf you're going on this show as a guest, expect some version of each of these. Each note explains when the host reaches for it.
origin
1- Q.01
“Tell us where you're from and how you got to founding your business.”
This is their standard opening question, used to frame the entire conversation around the guest's personal and professional origin story.
process
3- Q.01
“What was the transition like from a corporate job to running your own shop?”
Asked of guests who left stable careers, this question surfaces the mindset shifts and challenges of becoming an entrepreneur.
- Q.02
“What do you wish you'd known about getting the word out, and how do you do it now?”
This question seeks practical marketing and customer acquisition advice based on the guest's early struggles and current strategies.
- Q.03
“How do you create a good culture and maintain your staff?”
The hosts often ask this as a business grows to understand the guest's approach to leadership and team-building.
mindset
2- Q.01
“How did you know it was the right time to make the jump to full-time entrepreneurship?”
This follow-up probes the specific decision-making and risk-assessment process behind leaving a steady paycheck.
- Q.02
“How do you deal with negative comments or feedback?”
Asked to explore the emotional and strategic side of handling public criticism as a business owner.
personal
1- Q.01
“What were those difficult conversations with your wife/family like?”
A signature question that explores the personal and relational sacrifices involved in starting a business.
advice
2- Q.01
“What's your advice for young people just starting out?”
Towards the end of the interview, they often solicit direct, actionable advice for their audience.
- Q.02
“What are some key things a new business can do on the front end to avoid problems?”
This question aims to extract preventative, practical tips for new entrepreneurs from the guest's experience.
industry
1- Q.01
“What are you seeing in your industry right now?”
This question leverages the guest's expertise to provide the audience with an insider's view on market trends.
future
1- Q.01
“What have you seen regarding technology and the investment it takes for businesses?”
This question explores how technology, like AI, is impacting small businesses and the investment required.
Signature segments
- · Opening bourbon tasting and rating segment
- · "I'm Tyler and I'm Dakota and this is the Bourbon and Business podcast"
- · "Ways Energy Bourbon Break"
Topics covered repeatedly
Who gets booked here
The show books founders and owners of small-to-medium-sized businesses, with a noticeable number from the American South. Guests are typically on to tell their origin story and discuss the practical realities of building their company, from financial hurdles to company culture.
- Gray Welchon Episode 171 - Gray Welch - don't aim to people please
- Daniel Nicholsonon Episode 170 - Daniel Nicholson - strike when the iron is hot
- Duncan Welchon Episode 169 - Duncan Welch - know your numbers
- Elle Ingallson Episode 168 - Elle Ingalls - rewrite the story
- Elliott Godwinon Episode 167 - Elliott Godwin - like ironman
Where to find this show
Audience & reach
Sponsors include a hotel and vineyard in Mississippi, suggesting the show has a strong regional audience in the Jackson, MS area. This makes it a good fit for brands targeting that specific geographic market. The show's themes also align with financial services, business software, and spirits brands.
Subscriber and view counts are pulled live from YouTube and re-verified on a 30-day cycle. Listener estimates for the RSS feed aren't published here unless they're host-verified.
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People also ask
- Who are the hosts of Bourbon and Business?
- The hosts are Dakota Tate, a financial advisor with an MBA, and Tyler Wiltshire, an insurance agent and board member of the Rankin County Chamber of Commerce.
- What is the format of the show?
- Each episode begins with the two hosts tasting and rating a bourbon, followed by a long-form interview with a single guest, typically a business founder.
- Is the podcast still active?
- Yes, the podcast releases new episodes on a weekly basis.
- Where is the podcast based?
- The hosts and many of their sponsors are based in the Jackson, Mississippi area.
- What kind of guests do they have?
- They primarily interview founders and entrepreneurs of small to medium-sized businesses to discuss their origin stories and business philosophies.
Built from the show's public RSS feed, YouTube, the host's own websites, and the cited sources below. Computed and AI-extracted fields are labelled. Facts only — no private info, no fabrication, no transcripts republished.
Sources & how this page was built
This page is AI-assisted, grounded in the public sources cited below, and host-verifiable. We publish facts only; we do not republish transcripts. If anything here is wrong, the host can claim and correct the page above.Model: gemini-2.5-pro · high confidence
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