Episode Summary
How a process-driven advisor helps modernize a legacy wealth management firm. Jack Dobies shares his path from Ohio State and Deloitte as a software cloud engineer into financial planning at Merkel Wealth Management. He and Brian talk about why money is emotional, where AI can help and where it still falls short, and what clients really need beyond generic advice once their assets and complexity grow. Jack also explains how referral-driven firms think about growth, why some clients want control while others want full delegation, and how Merkel is approaching EOS, rebranding, and expansion in 2026.

Key Takeaways
A career shift from software to wealth management can be driven by the desire to see direct impact on people, not just systems.

Financial advice becomes part strategist and part therapist, because goals, values, and emotions shape decisions as much as math.

AI can assist with analysis, but oversight matters because confident errors can create real risk when money and timelines are involved.

Generic saving and investing guidance is easy to find, while planning for protection, taxes, and legacy is where complexity rises fast.

Client relationships vary by control preferences, so structuring a mix of advisor-managed assets and self-directed “fun money” can build trust.

Referral-driven growth works when trust is strong, and business and employer-sponsored planning can open a new lane for reaching people earlier.

EOS can help a legacy firm scale by making processes repeatable, even when change management requires patience and steady buy-in.

Timeline
Early
00:00:00 Jack’s background and the move from software and cloud engineering into wealth management
00:01:00 Joining a founder-led firm and bringing process and innovation into an established practice
00:03:00 Why financial planning feels more fulfilling, with multigenerational client relationships
00:05:00 Why firms feel pressure to modernize, and where AI creates fear and opportunity

Middle
00:06:00 What AI cannot replace yet, including emotional guidance and advanced planning needs
00:08:00 When generic advice is enough, and when planning becomes more valuable as assets grow
00:10:00 Using AI tools for portfolio analysis, plus the need to verify results with due diligence
00:11:00 Why confident mistakes in tools matter more when stakes are high

Late
00:15:00 Two client types, those who want to delegate and those who want to stay hands-on
00:17:00 How Merkel balances client control with advisory structure, including boundaries on trading requests
00:20:00 Referral-driven growth, business planning as an expansion path, and what CPAs do and do not cover
00:22:00 2026 priorities, CFP exam, clarifying the firm’s niche, and a full brand refresh
00:24:00 Building structure with EOS and managing internal change over time
00:26:00 How to reach Jack and Merkel Wealth Management

Links and Resources

LinkedIn: https://www.linkedin.com/in/jack-dobies/Company: http://merkelwm.com/

Episode Summary
How AI becomes a real operating system for small and mid-sized businesses. Wil Lavender shares his path from post-2008 finance roles and nearly 15 years in bank back-office technology to becoming employee number one at Agent700. He and Brian talk about why most SaaS tools force companies into a one-size-fits-all mold, and how AI can help businesses build custom solutions at lower cost. They also dig into tool lock-in, cost arbitrage, and why “digital employees” need feedback loops to improve. Wil closes with a practical example of turning policy binders into usable company-wide knowledge that actually influences decisions.

Key Takeaways
A shift from front office finance to back office technology can unlock a career focused on enabling outcomes through problem-solving.

AI-driven custom software can reduce dependence on expensive SaaS tools that were built for mass appeal, not one business.

Sovereignty matters because the “best” model changes fast, and staying flexible protects both performance and cost.

Costs are part of the AI equation, and being able to switch tools can become a real cost optimization lever over time.

Treating AI like digital employees reframes failures as inputs, because feedback and iteration are what make systems reliable.

Architecture and outcome clarity still matter, because AI can generate code while humans define what good looks like and why.

Global knowledge unlocks more than chatbots, because shared policies and context can shape decisions across teams instead of sitting in silos.

Timeline
Early
00:00:00 Wil’s path from finance interests into investment banking and prop trading after 2008
00:01:00 Discovering the appeal of back office problem-solving and technology enablement
00:02:00 Nearly 15 years building teams and solutions across banking support functions
00:03:00 Taking time off, consulting, then joining a startup as employee number one

Middle
00:03:00 What Agent700 is building, an AI-driven operating system with agentic capabilities
00:05:00 Why SaaS tools like CRMs can feel overbuilt and still miss what a business truly needs
00:06:00 Sovereignty and autonomy across AI providers, plus the rapid shifts in model leadership
00:07:00 Cost considerations, experimentation versus repeatable “brick laying,” and optimization

Late
00:09:00 Why AI-built software still benefits from expertise in debugging and architecture
00:10:00 Managing AI like digital employees, feedback loops, and working backward from outcomes
00:16:00 A practical use case, turning policy binders into global knowledge that guides decisions
00:20:00 Hiring cycles, the storming-to-performing curve, and why AI is driving hiring demand
00:22:00 What Wil is excited about in 2026 and how to reach him

Links and Resources

LinkedIn: https://www.linkedin.com/in/wil-lavender-36a636259/Company: https://www.agent700.ai/

Episode Summary
How to systematize marketing so teams stop reacting and start driving results. Taylor Edginton shares how he went from marketing technologist roles and startup experiences to becoming Digital Director at Reynolds+Myers. He and Brian dig into what a “marketing machine” really means, why iterative progress beats waiting for perfect launches, and how to choose channels based on where customers actually pay attention. They also talk about why email and content marketing feel harder than they used to, how bad advice spreads fast, and what makes 2026 feel like a year of disruption and opportunity.

Key Takeaways
A marketing machine is a system that replaces reactive, disconnected tasks with a clear direction tied to the market, customer, and business goals.

Progress compounds when teams ship improvements in stages, because real-world feedback arrives only after something is live.

Channel strategy gets simpler when it starts with the customer’s behavior, because “everywhere at once” usually creates shallow execution everywhere.

Email can still work, but blasting because sales needs a push trains audiences to ignore messages and weakens the relationship over time.

Content marketing has a higher bar today, and relying on “just write blogs for SEO” can become a long, slow grind without returns.

Big brands can break “best practices” and still win, so copying their tactics without their brand equity and scale often backfires.

Disruption forces change, and that pressure can open the door to faster modernization inside large, complex organizations.

Timeline
Early
00:00:00 Taylor’s background, Idaho roots, and early fascination with the internet
00:01:00 Marketing degree, fundamentals that still hold, and what college got right and wrong
00:02:00 First job in higher ed as the CRM guy, and becoming a marketing technologist
00:03:00 Moving to Boise, early internet work, and connecting with a software entrepreneur

Middle
00:04:00 Ping Plotter, the “No Pileups” car wash pivot, and a fast startup scaling experience
00:05:00 Joining Reynolds+Myers as Digital Director and the focus on legacy, complex businesses
00:08:00 Defining “marketing machine” versus reactive marketing, and why fundamentals come first
00:10:00 Triage and sequencing work so teams do one thing at a time and keep momentum
00:11:00 Launching imperfectly, learning faster, and why inaction creates permanently lost opportunity

Late
00:15:00 Timeless marketing principles, how people buy, and why the fundamentals keep repeating
00:18:00 Avoiding “everything everywhere,” focusing on where the audience is, and sustained execution
00:20:00 Email dilution, content marketing getting harder, and why some advice is outdated
00:23:00 Marketing guru dynamics, why context matters, and the danger of copying the wrong playbook
00:26:00 What feels different about 2026, quiet change, and finding opportunity in disruption
00:28:00 Where to find Taylor and closing thoughts

Links and Resources

LinkedIn: https://www.linkedin.com/company/reynolds-myers/Company: https://reynoldsandmyers.com/

Episode Summary
Caroline Colavita, VP of Marketing at Robard, shares how her career path shifted from retail buying into digital marketing and user experience, and why that background shaped how she thinks about conversion and growth. She explains what Robard does in weight management, how the rise of GLP-1 medications (like Ozempic) reshaped the industry, and why Robard chose to pivot into direct-to-consumer with a GLP-1-focused protein shake. Caroline also walks through the internal shift from B2B marketing for doctors and hospital systems to speaking directly to patients, including the testing mindset required to move faster, adapt messaging, and navigate ad platform compliance. The conversation closes with what she’s most excited about next: new product launches, major events, and expanding brand visibility nationwide.

Key Takeaways
Caroline’s entry into marketing came through e-commerce operations and user experience, giving her a conversion-first mindset.

Robard has historically served doctors, weight loss clinics, and hospital systems with on-site manufactured meal replacements and structured plans.

GLP-1 medications disrupted weight management, but also created a major opportunity for nutrition support, especially around protein and side-effect management.

Robard’s DTC pivot centered on collecting real consumer feedback first, then using that data to support adoption in the clinical channel.

Transitioning from B2B to B2C requires a different tone, faster iteration, and comfort with testing, failure, and constant revision.

Platform compliance matters: marketing in health/medication-adjacent categories changes what can be said and how targeting works.

AI is reshaping SEO and marketing workflows quickly, often requiring continuous adaptation across tools and platforms.

Timeline
Early
00:00 Introductions and Caroline’s role at Robard
00:30 From “assistant buyer” to e-commerce and UX
02:20 What Robard does and their 50th year milestone

Middle03:30 GLP-1 medications and how they changed the category
05:30 Why “just eating less” isn’t the same as changing behaviors
07:00 Caroline joins as the company accelerates toward DTC
08:00 Launching the Biocare website fast and learning compliance realities
09:40 Resetting a marketing plan, building a testing culture, and iterating quickly
12:00 Shifting tone from clinical B2B to consumer-first B2C

Late
16:40 DTC-first strategy: consumer feedback → proof points for doctors
18:00 “GLP-1 Blueprint” weekly guidance concept
19:10 Expanding beyond traditional channels into independent pharmacies
19:50 What’s next: events, travel, and new product launches
21:10 Where to find Caroline and Robard online

Links and Resources

LinkedIn: https://www.linkedin.com/in/caroline-colavita-a8450116/

Company: http://www.robard.com

Episode Summary
What it really takes to sell a privately held business, from readiness to closing. Peter Wright of Anderson LENEAVE and Company shares how lower middle market sell-side processes work, why many owners are not actually “sale-ready,” and what buyers look for when evaluating stability, leadership depth, and risk. He also breaks down where deals tend to come from, why timing the market is rarely the point, and what makes the process emotionally harder than most first-time sellers expect. Toward the end, Peter touches on how AI may change the mechanics of deal work while the human side stays essential.

Key Takeaways
Most owners will exit their business at some point, so responsible leadership includes planning for an unexpected transition.

A company where most customer relationships run through the owner looks more like a high-paying job than a transferable business.

In sell-side work, buyers are paying for durability, which means a credible team and continuity that outlasts the founder’s day-to-day presence.

Many sell decisions start with a trusted advisor conversation, often through a CPA, attorney, wealth manager, or other long-term relationship.

Trying to perfectly time the market matters less than being operationally ready and personally ready for what comes next.

The hardest part of selling is often emotional and experiential, even when the owner has been warned that the process will be demanding.

AI may streamline parts of diligence and research, but major transactions still hinge on trust, interpretation, and human decision-making.

Timeline
Early
00:00 Introductions and Peter’s background
01:00 Early career and Lionbridge growth through acquisitions
03:00 Building worldwide sales processes across cultures

Middle
05:00 What Anderson LENEAVE and Company does and who they serve
06:20 Why sell-side exits dominate and how succession gaps drive sales
09:00 How owners typically start the selling conversation and referrals happen
12:00 Why early exit planning is hard for smaller companies to fund
14:10 When a business is not ready to sell and the owner-dependence problem
17:00 Timing the market vs selling when the owner is ready

Late
19:00 How buyer perceptions shift by industry and the role of private equity
22:00 Why older-owner dynamics can slow investment and growth
22:40 AI and what it changes, and what it does not, in deal work
23:40 What Peter is focused on next and how to reach him

Links and Resources

LinkedIn: https://www.linkedin.com/in/peterwright1/

Company: https://www.andersonleneave.com/

Episode Summary
How Inflect markets a marketplace for digital infrastructure, with Chan Yu Kuo. Chan Yu Kuo, Director of Marketing at Inflect, walks through his path from medical equipment to tech and explains Inflect’s marketplace and advisory model for helping buyers compare options like colocation, bare metal, GPU cloud, and connectivity. He and Brian dig into why many buyers know the outcome they want but struggle to define the right infrastructure, then shift to what is working in a noisy market, including SEO as “search everywhere,” partner-driven insight, and tightly targeted paid search. They also discuss how AI overviews are changing top-of-funnel content and why middle- and bottom-funnel specificity is gaining importance.

Key Takeaways
Broad experience across roles and industries can sharpen marketing judgment because it builds a fuller view of how the business works end to end.

A marketplace model can reduce friction in technical buying by enabling self-research, side-by-side comparison, and expert validation when requirements are unclear.

In infrastructure purchasing, the real job is often translating a desired outcome into a workable setup, then using examples and prior use cases to close the gap.

In 2026, “SEO” increasingly means building discoverability across channels and communities, since attention and AI-driven discovery pull from many sources.

Paid ads tend to perform better when they focus on buyers showing clear intent, such as transactional keywords and mid-funnel readiness, rather than broad awareness targeting.

AI is compressing “what is” content into the search results themselves, which raises the value of deeper, experience-based content that explains how decisions get made and how results were achieved.

Timeline
Opening and background
00:00:00 Brian welcomes Chan Yu Kuo and sets the stage
00:01:00 Chan shares his cross-industry path and how it shaped his marketing approach
00:02:00 Chan describes his earlier work in medical equipment marketing

Inflect and the marketplace model
00:03:00 Chan explains what Inflect does and the “Expedia” analogy for digital infrastructure
00:04:00 Why buyers often do not know what they need, and how self-research fits the journey
00:05:00 How Inflect uses an AI agent and advisory support to help buyers move forward
00:07:00 A walkthrough of the typical colocation buying process and how Inflect changes it

Marketing, AI, and what is working now
00:11:00 Chan frames 2026 marketing around creativity, tool architecture, and clear communication
00:12:00 “Search everywhere” optimization and why presence across platforms matters
00:14:00 What is driving growth now, including paid search and testing Reddit ads
00:19:00 How AI overviews reduce top-of-funnel clicks, and why mid-funnel depth matters
00:21:00 Chan’s outlook for 2026 and the rising infrastructure demand behind AI adoption

Wrap-up
00:23:00 How to find Inflect and what listeners can do next

Links and Resources

LinkedIn: https://www.linkedin.com/in/chanyukuo/

Company: https://www.linkedin.com/company/inflect-inc/

Episode Summary
Inside cannabis manufacturing and terpene extraction with Jarod Noble Harvey. Jarod shares how he went from early cultivation in California to building labs, optimizing operations across state markets, and focusing on cannabis-derived terpene extraction. He and Brian dig into the realities of a patchwork regulatory system, how testing and compliance differ by state, and why standardization matters for safety and industry leadership. Jarod also explains how companies look for short-term competitive footholds in crowded markets and what he is watching globally in the EU, Latin America, and beyond.

Key Takeaways
Cannabis operations reward modularity and agility because products, rules, and competition change quickly across states.

State-by-state regulations tend to share a baseline, but oversight, audits, and third-party testing requirements create meaningful differences.

In a young industry, product direction and innovation often came from operations leaders before formal marketing teams became common.

Closing testing loopholes can improve safety and trust, while process controls and compliant category shifts can extend product viability.

Terpene extraction, especially cannabis-derived terpenes, is positioned as a major driver for modulating flavor and consumer experience.

Federal inaction leaves the US with fragmented rules, which shapes where companies invest and how they plan for uncertainty.

Global markets with clearer structures, including parts of the EU and emerging exporters, may move faster by building on earlier industry lessons.

Timeline
Early
00:00:00 Brian welcomes Jarod and asks how he got started
00:01:00 Moving from cultivation into extraction and manufacturing
00:02:00 Building labs and shifting to more tightly regulated markets

Middle
00:03:00 Navigating the patchwork of state regulations and oversight
00:04:30 How product innovation and marketing evolved in cannabis
00:05:30 Operational efficiency, modular systems, and terpene extraction focus
00:07:00 Testing loopholes, advocacy, and compliant ways to extend product life
00:09:00 The role of science in competitive advantage and consumer outcomes

Late
00:12:00 Looking outside the US, EU activity, and global trade opportunities
00:13:30 Jarod’s view on the public debate, safety, and potential for abuse
00:15:00 Why broader legality and standardization matter for safety and leadership
00:17:00 Who Jarod helps and what it takes to survive in the industry
00:20:00 What he is excited about in 2026 and how to contact him

Links and Resources

LinkedIn: https://www.linkedin.com/in/jarodnobleharvey/

Company: https://www.pivot-manufacturing.com/

Episode Summary
David Greenberg breaks down how private trusts can help protect assets and create privacy for families and business owners. He shares how early sales and computer skills shaped his path, the leap into entrepreneurship in 2007, and why Freedom Studio focuses on both growth and defense. The conversation covers separating control from beneficial use, how commercial liability shows up through taxes, regulation, and lawsuits, and what it can look like to learn or implement these systems. David also explains how Freedom Studio educates through public content and low-cost memberships, then supports faster hands-on setups. What changes when you start thinking about protection before problems show up?

Key Takeaways
Early exposure to selling and technology can compound into a career built around both business development and systems thinking.

Protecting assets involves more than physical risk, it also includes commercial liability like taxes, regulation, and lawsuits.

A trust structure can separate legal control from beneficial use, which changes where liability sits and how assets are defended.

Education lowers the trust barrier for unfamiliar financial and legal frameworks, especially when concepts are introduced publicly and then explored privately.

Doing it yourself can work, but guided implementation can compress timelines dramatically when founders and families want protection in place sooner.

Private conversations and discretion matter in this space, since many strategies are intentionally not discussed publicly in detail.

Timeline
Opening
00:00:00 Brian welcomes David Greenberg and introduces Freedom Studio
00:00:24 David shares how he started selling greeting cards at 11

Background and the shift to entrepreneurship
00:01:21 David describes studying computer science and working in industry
00:02:00 David explains going all-in on entrepreneurship in 2007
00:02:33 How Freedom Studio evolved over the last several years

What Freedom Studio does
00:03:15 “An incubator for greatness” that also focuses on protection
00:03:44 Using private trusts and trustees to protect assets and build privacy
00:05:03 How David evaluates whether founders and families are a fit

Trust basics and the protection framework
00:06:02 Why all assets need layered protection, including commercial liability
00:07:00 Separating ownership from control as the core concept
00:08:00 Legal title vs beneficial use, explained through a house example
00:10:44 When to consider trusts, and why waiting can be costly

Education, implementation, and adoption
00:13:05 Why fewer businesses use these structures, and the role of discretion
00:18:00 How Freedom Studio educates through YouTube, LinkedIn, and courses
00:19:00 Courses teach the full process, with services available for speed
00:21:00 Typical implementation investment range and a one-to-three-month setup

Wrap-up
00:23:00 What David is excited about in 2026 and meeting clients in person
00:24:00 How to connect with David and find Freedom Studio resources

Links and Resources

LinkedIn: https://www.linkedin.com/in/david-greenberg-educator-the-freedom-studio/

Company: https://www.linkedin.com/company/the-freedom-studio/

Episode Summary
Dany Conti shares how she built Builder Supply Group from an empty showroom into a growing supply partner for builders. She walks through her start in small-company operations, the early one-woman grind, and the decision to control the supply chain by importing directly from factories to give customers clearer timelines. Dany also explains how key hires, and later bringing her husband into the business, helped reduce burnout and sharpen focus on operations, service, and strategy. The conversation closes on what she is watching in Austin’s market and what comes next with e-commerce.

Key Takeaways
Early-stage momentum can come from doing whatever the business needs, then gradually replacing your weakest areas with the right specialists.

Controlling more of the supply chain can turn “we do not know” into specific, usable updates that help builders plan and avoid delays.

Trust is a management filter, especially in sales roles where autonomy is required and constant oversight breaks the model.

Being an extension of the customer’s team can mean solving problems adjacent to your product, like helping unblock a project that has stalled.

Operational services like receiving, labeling, palletizing, and staging materials can remove real friction for small builders who lack storage and admin capacity.

Mixing family and business raises the stakes for culture, which can push owners to prioritize a sustainable, enjoyable workplace for the team.

Word-of-mouth can build a strong base, but growth eventually demands deliberate marketing so the right customers discover you sooner.

Timeline
Early
00:00:00 Introducing Dany Conti and Builder Supply Group
00:01:00 From business administration to learning every part of a small construction company
00:03:00 Starting with an empty showroom and selling before the space looked established
00:04:00 Why importing directly matters for supply-chain clarity

Middle
00:05:00 Growing from a one-woman show to adding a designer and building a sales function
00:07:00 What went wrong with early sales hires and why trust mattered
00:09:00 Burnout, loneliness at the top, and inviting her husband into the business
00:11:00 How that change affected motherhood, work, and continuity in the company

Late
00:12:00 Competing by staying human, caring fast, and jumping in to solve client problems
00:15:00 Building services around real builder pain points like warehousing and design support
00:18:00 The marketing challenge of being the new option in a legacy vendor market
00:20:00 Rules for separating work and home, and how they handle balance
00:22:00 Looking ahead to 2026 and what she hopes shifts in the Austin market
00:23:00 How to reach Builder Supply Group, and the planned House of Tile e-commerce launch

Links and Resources

LinkedIn: https://www.linkedin.com/in/dany-conti-704b0147/

Company: https://www.buildersupplygroup.com/

Episode Summary
How a CRO builds cohesive growth from first customers to scale with fewer internal silos. Brian Felker shares his path from freight brokerage to leading go-to-market teams, then consulting through the uncertainty of 2020. He breaks down why early-stage companies shift from generalists to specialists, how “people problems” surface during growth, and why a single owner for the full customer journey can prevent marketing, sales, and customer success from working at cross purposes. Brian also explains where consultants can and cannot help, plus what he is most excited about at AgZen.

Key Takeaways
Starting in a high-pressure, commission-driven sales environment can build durable skills in work ethic, customer service, and performance transparency.

As companies scale, the work changes from everyone wearing multiple hats to specialists owning functions, which forces cultural and leadership adjustments.

If every leader around the table is in the biggest role they have ever had, growth gets harder. Experience helps teams anticipate common scaling pitfalls.

A Chief Revenue Officer can align marketing, sales, customer success, and partnerships around one customer journey so the story stays consistent end to end.

Selling more does not only grow revenue, it magnifies product and process issues already in the system, so it is better to find leaks early.

Consultants can help refine ICP, personas, messaging, and customer-value proof once there is a base of paying customers, but founders usually need to win the first customers themselves.

“Product-market fit” is often misunderstood. Consistent value and repeatable acquisition and retention matter more than optimistic signals.

Timeline
Early
00:00:00 Brian Felker’s roles, CRO at AgZen and founder of Growth Nerd
00:00:30 From psychology and college basketball to sales in freight brokerage
00:02:00 Building teams and opening offices, then moving into tech roles

Middle
00:05:00 What logistics teaches about competition, relationships, and performance management
00:07:30 Why consulting started in April 2020 and what patterns show up across companies
00:09:00 How growth shifts teams from generalists to specialists, and why culture gets harder
00:12:30 The value of leaders who have “seen this before” during scaling

Late
00:14:00 What a CRO owns across marketing, sales, customer success, and partnerships
00:16:30 Revenue growth can intensify product and delivery problems if the funnel is leaky
00:18:00 When a consultant helps and when founders need to sell the first customers
00:20:00 Founder optimism, the gray area of product-market fit, and consistency of value
00:22:10 What Brian is excited about building at AgZen
00:23:00 Where to find Brian and learn more

Links and Resources

LinkedIn: https://www.linkedin.com/in/brianwfelker/

Company: http://www.agzen.com/