The Unshakeables – "Is AI Here to Help You Grow, Build, or Replace Your Business?"

Live from SXSW | April 7, 2026
Host: Ben Walter (CEO, Chase for Business)
Co-host: Kathleen Griffith
Guest: Oz Velasian (CEO & Co-Founder, Kaleidoscope)

Episode Overview

This special episode, recorded live at SXSW 2026, explores the rapidly evolving intersection of artificial intelligence (AI) and American small business. Host Ben Walter, co-host Kathleen Griffith, and guest Oz Velasian (an Emmy- and Peabody-winning journalist and small business founder) discuss how AI is already reshaping business growth, operations, and competition. The conversation demystifies AI for small business owners, highlights real-world applications, and provides actionable steps for listeners to harness AI’s potential.

Key Discussion Points & Insights

The State of AI and Small Business (00:04–03:44)

• AI as a Game-Changer:
  Ben Walter lays out data: 59% of small businesses see AI as essential to their future competitiveness, and 61% think it will increase efficiency. Given that small businesses represent 44% of American employment, AI’s impact has national significance.

• Phases of AI Adoption:

  • 2024: Experimentation – “just try some stuff”
  • 2025: Early Execution – “do some stuff”
  • 2026: Value Delivery – “deliver, get value from the stuff you’re doing” (00:50)

• Unique Perspectives:

  • Ben: Macro, financial, survey/data-driven view
  • Kathleen: On-the-ground with business owners
  • Oz: Both technologist and founder

AI on the Ground: What’s Changing? (03:44–09:04)

• Recent Game-Changers:
  Oz highlights “Claude Code” as a recent watershed (03:58–06:01):

  “I think, and this is a bolder call than I would normally make, I think the world did actually change in the last three months. … You have real people, real small business owners, real employees … taking Claude Code, playing around with it to create applications and finding that it worked.” (04:10)

• From FOMO to Action:
  Oz shares how fear of missing out (FOMO) is now “productive,” driving tangible AI adoption among small businesses.

• Shifting Concerns:
  Kathleen underscores anxiety amid rapid changes and viral headlines (06:06):

  “We just saw Jack Dorsey lay off 40% of his whole team in one day … Matt Schumer's viral essay…The Atlantic's article that the US is not prepared for what it's going to do to US jobs. … It’s enough to give you acid reflux, like it really is.” (06:10)

• Tool-Sharing & New Norms:
  Owners are pragmatically trading notes on which tools and AI agents to use.

• Generative Video’s Impact:
  Kathleen gives the Original Tamale Company’s viral campaign (22M views) as an example of AI-driven business transformation, noting such breakthroughs will soon be more common (07:10–08:30).

Human Connections vs. Efficiency: Balancing Act (09:04–10:23)

• Fear of Losing the Human Touch:
  55% of surveyed business owners worry AI might erode the personalized connections that are their “moat” (09:10).

• Entrepreneurial Dynamism:
  Reduced cost of launching new ventures means more people can try starting second or third businesses. AI makes launching and running new businesses easier, but also drives competitive disruption (09:19).

What’s Obvious—and What Isn’t—About AI Use (10:23–14:36)

• AI’s “Superpower” Effect:
  Kathleen:

  “…the greatest personal amplification tool we will see in our lifetimes. … All of a sudden we woke up, and we were superhuman.” (10:23)

• No One-Size-Fits-All Playbook:
  Tool usage changes rapidly (from Claude Code, to Gamma, to Lovable, etc.) and there’s no standard approach.

• Leaders Lagging in Adoption:
  Many leaders don’t “walk the walk”—teams use AI, but top execs often don’t (11:15).

  Oz:

  “There’s a lot of ‘do what I say, not do what I do.’” (11:25)

• Content Creation to Operations:
  Content creation is the first widely adopted use (e.g., auto-generating video, clips, captions), but the real untapped opportunity is in systems and operations (automated sales, customer service, process automation) (11:28).

• Trust, Safety, and Data Barriers:
  Highly regulated industries (healthcare, legal) are slower adopters for privacy, legal, and cultural reasons (14:54).

Small vs. Big Business: Who Has the Edge? (18:30–20:54)

• David vs. Goliath, Tech Edition:
  Ben notes that while big businesses invest billions in proprietary AI, small businesses benefit from their nimbleness and new, widely available off-the-shelf tools (18:30–19:18).

  Kathleen:

  “You are all of a sudden able to be a solopreneur, single founder and have an entirely AI-generated business. I mean, that is so bonkers.” (19:18)

• Power Shift Toward the Individual:
  Smaller players can now operate as if they have a full team, thanks to AI, shifting the entrepreneurial landscape.

• Historical Echo:
  Oz points out that today's AI leaders (Anthropic, OpenAI, DeepMind) started as small businesses now running the largest value-creation engines globally (20:14).

Real-World Applications: Case Studies (20:54–26:42)

• Apogee Healthcare (21:37):
  Uses AI to match dementia patients with ER video care, speeding up hospital triage and lowering costs.

• Marketplace for Secondhand Bikes (22:00–22:47):
  Developed an AI-powered pricing system to objectively value bikes, dramatically shortening sale cycles.

  Oz:

  “Creating an AI tool that essentially took the bike and created a data driven price comps report … reduced the time to getting a realistic price...by an extraordinary amount.” (22:47)

• Meeting Optimization Tool:
  Small business CEO built a system to auto-collate live data from various sources, generating concise reports for executive meetings, ensuring actionable, data-driven discussions (23:00–24:05).

• Partake Cookies:
  Implements AI for financial modeling and robust sales forecasting, allowing the team to test different business scenarios (24:07).

• Nerdwax:
  Uses AI to accelerate product design (from A/B to A-Z testing) and process customer feedback more efficiently (25:02).

• Gretna (Manufacturing):
  Founder uses AI as a “business coach” and strategic sparring partner for annual planning and growth strategies.

• Vessel (Battery Storage):
  Employs AI for in-depth market research and competitive analysis (25:07–26:42).

  Kathleen:

  “…they're just kind of like running fearlessly head first into AI. … I think that just speaks to the entrepreneurial spirit of ‘I'm going to break things, I'm going to try to figure it out, I don't know what I'm doing.’” (26:28)

Actionable Advice for Small Business Owners (26:42–29:20)

• Oz’s Advice:

  “Yesterday is better than today, today is better than tomorrow, and tomorrow is better than never. … There’s no small business which doesn’t have a somewhat repetitive, time-sucking task … that’s a great place to experiment with an AI tool.” (26:59 & 28:00)

• Kathleen’s Advice:

  “Practice, practice, practice. … 30 minutes a day for the next 30 days...make a video, create a sales agent, build a presentation using AI. … You’ll be blown away by what you learn about yourself and what it’s able to do for your business.” (28:19)

• Ben’s Advice:

  “Leverage your employees. Ask all your employees what are the two or three tasks that they hate the most at work and then challenge them to solve those with AI … it’s a way for them to stop doing things they hate.” (28:43)

Notable Quotes & Memorable Moments

• Oz Velasian on Claude Code’s Impact:

  “We are on a rocket ship. And ... If I don’t [adopt AI], it’s on me.” (05:58)

• Kathleen Griffith on Entrepreneurial Anxiety:

  “It’s enough to give you acid reflux, like it really is.” (06:23)

• Ben Walter on Growth vs. Efficiency:

  “If you asked any small business owner … what would you rather have, a business that is the same size but half the cost structure … or a business that is double the size at the same margin … you take the latter every time and twice on Sunday.” (15:52)

• Kathleen Griffith on AI’s Potential:

  “All of a sudden we woke up, right, and we were superhuman.” (10:27)

• Oz Velasian on Adoption Lag:

  “There’s a lot of ‘do what I say, not do what I do.’” (11:25)

• Ben Walter on Small Business Opportunity:

  “I can feel it in my bones that this is a moment for small business in terms of the adoption of these tools.” (29:05)

Key Timestamps

• 00:04–03:44: Setting the scene – small business, AI survey stats, and guest intros
• 03:44–06:01: Recent inflection points in AI adoption ("Claude Code" impact)
• 06:06–09:04: AI’s growing urgency and generative video’s viral business effects
• 09:04–10:23: Fears about losing “human touch” in business
• 10:23–14:36: Content creation to real operations; adoption chasm for leaders & industries
• 18:30–20:54: Small business vs. Big business – who benefits most from AI?
• 21:37–26:42: Real-world AI examples from healthcare, consumer goods, manufacturing
• 26:42–29:20: Final quick-win advice for small business owners

Closing

The episode emphasizes that AI adoption is no longer optional but imperative. The hosts and guest deliver optimism and urgency, offering pragmatic strategies to help small businesses leverage AI for growth, efficiency, and creativity—while keeping the human element at the core of what makes a business “unshakeable.”