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This week, Jack Sharry talks with Stephen Chen, Founder & CEO of Boldin. Stephen is a classic entrepreneur who takes…

Episode 114: This week, Kyle Van Pelt talks with Torie Happe, Head of Partnerships at Holistiplan. Torie began her career at LPL Financial, where she managed new accounts, led RIA conversions, and developed new operational procedures. In 2016, Torie transitioned into fintech at Riskalyze. She later held leadership roles at FIX Flyer and Onramp Invest before joining Holistiplan in 2022 as Head of Partnerships.

Kyle and Torie discuss how Holistiplan enables advisors to turn complex tax returns into clear, actionable plans. Torie also discusses the difference between tax planning and tax advice, how firms can bridge that gap, and where Holistiplan seamlessly integrates into an advisor’s tech stack. Torie also talks about Holistiplan’s academic program, which provides hundreds of students with free access to the firm’s award-winning software and a certification course to enrich their curriculum and credentials.

In this episode:

(00:00) – Intro

(02:18) – Torie’s money moment

(06:16) – How Holistiplan has gone viral in the fintech space

(08:04) – Making taxes simple and meaningful for clients

(10:03) – The difference between tax planning and tax advice

(11:40) – How advisors use Holistiplan alongside other tools

(15:55) – Holistiplan’s academic program

(19:49) – Torie’s outlook on the future of the industry

(22:09) – Torie’s Milemarker Minute

Key Takeaways

Simplicity wins. Magic happens when you make complex financial concepts simple enough for clients to actually understand and engage with.

Use technology as a bridge, not a barrier. Fintech tools like Holistiplan are there to enhance advisor-client relationships, not replace them.

Plan first, execute second. Tax planning lays out the “what-ifs.” Tax advice executes the “what now.” Small firms can thrive by focusing on that planning layer before involving a CPA.

AI is powerful, but people are irreplaceable. While AI can streamline workflows, clients will still want authentic, face-to-face interaction with their advisors.

Quotes

“We took something really complicated (tax) and made it really simplistic for an advisor to understand.” ~ Torie Happe

“Tax planning is really just planning for your life. What are you doing with every dollar you’ve spent or will spend this year? The tax advice piece is that execution piece, and that’s where you’re going to your tax professional to execute on the plan that your advisor has built.” ~ Torie Happe

“Clients actually want to talk to a human. You’re dealing with their everyday money and their lifestyle. They don’t want to just be automated into whatever email campaigns or text messages you’re going to send out.” ~ Torie Happe

Links 

Torie Happe on LinkedIn

Holistiplan

Nitrogen

The Outsiders

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Milemarker.co

Kyle on LinkedIn

Jud on LinkedIn

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Produce game-changing content with Turncast

Turncast helps your company grow by producing top-quality content and fostering transformative conversations. We specialize in content generation, podcasting, digital strategy, and audience growth for fintech and financial services companies. Learn more at Turncast.com.

Milemarker Layers Launch, Organic Growth & Modernizing Your RevOps

This week, Jack Sharry talks with Rob Pettman, President of TIFIN. Rob brings more than 20 years of leadership experience…

Episode 113: John Bunch, CEO of Allworth Financial. With over 30 years in financial services, John has guided firms through big transitions, from founder succession and acquisitions to private equity cycles and scaling operations, while preserving their culture. 

This week, Kyle talks with John about leading Allworth into its third generation. John reflects on lessons from Schwab and other founder-led firms, and how Allworth is balancing organic growth with strategic acquisitions. He explains the importance of culture, integration, and advisor support, while also detailing the firm’s investments in tax services and AI innovation. From client-centric models to the future role of advisors as coaches, John offers an inside look at building enduring growth in a rapidly changing RIA landscape.

In this episode:

(00:00) – Intro

(02:11) – John’s money moment

(04:07) – Allworth’s third-generation growth strategy: Evolve, Elevate, and Execute

(04:51) – The holy grail of financial services

(07:04) – Allworth’s organic growth strategy

(09:29) – John’s growth mindset

(12:29) – What it’s like to work with industry legends

 (16:09) – Why RIAs are moving into tax services

(19:10) – The power of specialized teams

(22:02) – How Allworth manages multiple tech stacks

(24:16) – Allworth’s approach to AI adoption

(28:31) – John’s thoughts about the future of the industry

(30:35) – John’s Milemarker Minute

Key Takeaways

The holy grail in this industry is organic growth. Acquisitions help, but building scalable, client-centered growth engines is what drives long-term value.

Don’t focus on what you spend on growth. Focus on the payback. If a channel is working, invest more in it. A supportive board will always back a strategy with a good return on investment.

Be a “fiduciary to their dreams.” When acquiring a founder-led firm, respect their legacy and understand that they built the business to help people. Frame the future as a partnership and be willing to adopt the best ideas, regardless of where they come from.

Embrace AI now or get left behind. Firms that fail to strategically adopt AI will be at a disadvantage. Start experimenting and integrating it into your operations, from client service to advisor dashboards, and see how it can help you get more insights.

Quotes

“The holy grail in this industry is organic growth. That’s what drives valuations. And if you get that right, you’re building a scalable business for the future.” ~ John Bunch

“If you’re not willing to evolve your business and elevate how you meet with your clients, you’re going to be in a bit of trouble. The winners in the long term in this industry are going to be the folks who can grow organically.” ~ John Bunch

“Advisors will be more like counselors and coaches on a wide variety of things than they will be on experts on cash flow or investments. And the firms that actually help their advisors move in that direction are going to be the winners.” ~ John Bunch

Links 

John Bunch on LinkedIn

Allworth Financial

Pat McClain

Scott Hanson

Darla Sipolt

Charles Schwab

Jump AI

Atomic Habits

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Milemarker.co

Kyle on LinkedIn

Jud on LinkedIn

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Produce game-changing content with Turncast

Turncast helps your company grow by producing top-quality content and fostering transformative conversations. We specialize in content generation, podcasting, digital strategy, and audience growth for fintech and financial services companies. Learn more at Turncast.com.

Behind the Scenes of Altruist, Album Releases, Transforming Your Fee Billing and More

This week, Jack Sharry talks with J. Womack, Head of Asset & Income Optimization at SEI. In his role, J.…

Episode 112: This week, Kyle Van Pelt talks with Jason Wenk, Founder and CEO of Altruist. Jason has lived and breathed the financial services industry over the last 20 years as a financial advisor, investment systems developer, analyst, and founder.

Jason shares his journey from humble beginnings to building some of the fastest-growing RIAs. From his early days at Morgan Stanley to pioneering digital marketing for his own RIAs, Jason discusses the innovations that led to the founding of Altruist. Jason also explores the power of content and why social media platforms are today’s hub for advisor growth.

In this episode:

(00:00) – Intro

(02:44) – Jason’s money moment

(05:21) – From intern to industry disruptor: Jason’s path to building two RIAs

(13:56) – Jason’s digital marketing playbook

(17:38) – Where attention is won: YouTube, TikTok, referrals, and more

(25:02) – Why offline marketing still crushes in 2025

(28:05) – The pain points that led Jason to create Altruist

(34:12) – How Altruist is using AI to transform advisor workflows

(43:06) – Jason’s Milemarker Minute

Key Takeaways

Leverage digital marketing. Blogging and creating videos on social media build authority and trust.

Play the long game. Social media platforms can drive billions in new business. But when they eventually get crowded, differentiation comes from client experience and outcomes, not just marketing tactics.

Know your audience. AI and SEO shifts may impact younger investors, but retirement-age clients still search the old-fashioned way. Tailor your approach to the people you want to reach.

Consistency wins. Whether it’s local seminars, radio shows, or social media content, firms that pick a lane and execute with discipline tend to outpace the rest.

Quotes

“A lot of our fastest-growing advisors are using YouTube as their primary mechanism to be in front of new clients. We have a few who are using social media, so they’re active on X, some are heavy on LinkedIn, and we’re starting to see some who are actually doing decent volume from TikTok.” ~ Jason Wenk

“Our generation is open about how and what we do. We all have an abundance mindset, and we share and love celebrating everybody else’s wins.” ~ Jason Wenk

“In a world where it’ll be nearly impossible to be different and unique based on your content, what you actually deliver will matter a lot more. Driving the best outcomes and the best experience will become a differentiator. ” ~ Jason Wenk

Links 

Jason Wenk on LinkedIn

Altruist

Morgan Stanley

AI Assistance – Altruist

Elon  Musk

Connect with our hosts

Milemarker.co

Kyle on LinkedIn

Jud on LinkedIn

Subscribe and stay in touch

Apple Podcasts

Spotify

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Produce game-changing content with Turncast

Turncast helps your company grow by producing top-quality content and fostering transformative conversations. We specialize in content generation, podcasting, digital strategy, and audience growth for fintech and financial services companies. Learn more at Turncast.com.

Milemarker’s Latest Release, Behind the Scenes with CityWire’s Chief Editor, and Milemarker Grabs 4 Luminary Nominations

Scott Smith is the Senior Director of Advice Relationships at Cerulli Associates, where he leverages deep research and analysis to…