Don't Do That

Are you compromising your company's culture by hiring brilliant jerks? 

In this episode of Don't Do That, host Kelly Waltrich is joined by Ainslie Simmonds from BNY to discuss the importance of hiring for culture, avoiding toxic influences, and the power of loving the problem rather than the answer. 

Ainslie shares her journey from the fintech world to starting a fintech within BNY Mellon, outlining her insights on innovation, advisor productivity, and cultural transformation. She emphasizes the key to success is surrounding yourself with the right people and avoiding those who may be talented yet damaging to team dynamics.

Kelly and Ainslie discuss:

00:01 Ainslie Simmonds' passion for advisor productivity
00:51 Introduction to the episode and Kelly's no-nonsense approach
1:42 Ainslie's journey and the challenge of building tech at BNY
3:39 Unpacking the "swivel chair" problem for advisors
4:12 The conversation that prompted Ainslie to tackle big fintech challenges
4:52 The birth of Wove, an innovative wealth platform 
7:11 The culture shift within BNY and its impact on wealth management 
11:12 Facing industry giants in fintech 
12:26 The philosophy of "love the problem, not the answer" 
17:17 Ainslie's personal 'Don't Do That'—Avoid brilliant jerks 
18:48 Techniques for identifying toxic hires 
20:28 Kelly and Ainslie's tips for aligning team dynamics and culture 
29:02 The significance of culture in startups and transformation

Connect with Kelly Waltrich: 

• LinkedIn: Kelly Waltrich
• LinkedIn: Intention.ly
• X: Intention.ly
• Instagram: Intention.ly

Connect with Ainslie Simmonds: 

• LinkedIn: Ainslie Simmonds 
• LinkedIn: BNY
• Website: BNY

About Our Guest:

Ainslie Simmonds is a Managing Director and member of the Executive Committee for BNY Pershing. As Head of Global Strategy, Ainslie is responsible for strategy formulation and articulation, market and competitive analysis, business intelligence, corporate development and strategic partnerships. She is also President of BNY Pershing X, a business unit that designs and builds innovative digital solutions for BNY Pershing’s Wealth Solutions clients, including broker dealers, registered investment advisors (RIAs) and trust companies.

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Is your firm too focused on acquisitions while neglecting the power of organic growth? 

Kelly Waltrich welcomes John Wernz, a "reformed CMO" who now works with private equity firm Great Hill Partners as an Entrepreneur in Residence. Together, they explore a common pitfall in the financial advisory industry: prioritizing acquisitions and inorganic growth at the expense of developing strong organic growth capabilities. John shares insights from his experience working with firms looking to grow organically and sitting on several industry boards, offering a valuable perspective on balancing growth strategies.

Kelly and John discuss:

0:32 John's current role at Great Hill Partners 
1:56 The problem of firms skipping foundational marketing and jumping straight to advanced strategies
4:09 Indicators that show a firm is ready for organic growth investment 
5:02 The most common successful marketing channels for advisory firms 
6:13 Realistic marketing budgets for firms 
8:16 The often-overlooked "soft costs" of implementing marketing strategies 
9:20 The importance of having firm leadership involved in marketing efforts 
10:03 Why both John and Kelly appreciate working with empowered marketing roles 
13:21 John’s "Don't Do That": Getting caught up in inorganic growth at the expense of organic growth 
15:26 Why some firms rush to acquisitions before establishing their core marketing 
16:38 How to determine if your firm is ready for M&A
19:22 The need to have a defined marketing playbook before pursuing acquisitions 
20:18 Why an acquisition integration plan must include organic growth targets 22:06 The benefits of applying recruitment marketing principles to M&A 
26:25 John's Final advice

Connect with Kelly Waltrich: 

• LinkedIn: Kelly Waltrich
• LinkedIn: Intention.ly
• X: Intention.ly
• Instagram: Intention.ly

Connect with John Wernz: 

• LinkedIn: John Wernz
• LinkedIn: Great Hill Partners 
• Website: Great Hill Partners 

About Our Guest: 

With over 25 years of experience in leading and transforming marketing and growth strategies for various businesses, John is currently an Executive in Residence at Great Hill Partners, a private equity firm that invests in high-growth companies in the financial services, technology, consumer, and healthcare sectors. 

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Are you limiting your growth potential by thinking too small? 

In this episode of Don't Do That, host Kelly Waltrich sits down with Billy Hopkins, CEO of Silver Oak Securities, to discuss the importance of thinking big, taking uncomfortable steps, and adopting an enterprise mindset to accelerate business growth.

With 25 years of experience building Silver Oak Securities from a small Tennessee firm to a thriving enterprise, Billy shares his "Dave Grohl moment" that changed everything and the pivotal decisions that transformed his business.

Kelly and Billy discuss:

0:44 Introduction to Billy Hopkins and his Eagles fandom
1:47 Billy's journey from independent advisor to CEO of Silver Oak Securities
3:43 The "Dave Grohl moment" that changed Billy's entrepreneurial trajectory
6:25 Why holding onto unprofitable relationships limits your growth
9:12 Breaking through the ceiling: Investing in growth even when you don't feel ready
14:19 The value of being uncomfortable and having people who push you forward
17:57 Why advisors need to believe in their ability to elevate their practice
19:21 The importance of focusing on advisor experience to enhance client experience
21:43 Why partnerships and vendor relationships require patience to realize their full value
23:13 The wealth transfer opportunity and building the right infrastructure to capitalize on it
24:08 Billy's growth mindset: "Put a zero on the end of it"

Connect with Kelly Waltrich: 

• LinkedIn: Kelly Waltrich
• LinkedIn: Intention.ly
• X: Intention.ly
• Instagram: Intention.ly

Connect with Billy Hopkins: 

• LinkedIn: Billy Hopkins 
• Website: Silver Oak Securities 

About Our Guest: 

Billy Hopkins is the CEO & Founder of Silver Oak Securities, Inc, an independent, full-service Broker Dealer and SEC Registered Investment Advisor championing the spirit of independent wealth advisors by empowering them to foster meaningful, long-lasting relationships with their clients.

Billy has devoted the past 23 years to cultivating a unique structure at Silver Oak Securities that offers the strength, scale and resources of a large financial institution with the flexibility and freedom offered by smaller boutique organizations. 

Billy holds a degree in Business from Lambuth University, and holds his Series 6, 7, 4, 53 and 66. An avid trail runner, he lives in Tennessee with his wife, Rachel, and their sons, Sam and Jude.

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Think having the best idea guarantees success? Think again. 

On this episode of the Don’t Do That podcast, Kelly Waltrich and Brian Portnoy, CEO of Shaping Wealth, explore why great ideas alone aren't enough and how to ensure your message actually lands with your audience. 

Brian shares hard-earned insights from his 30-year journey from academia to entrepreneurship, revealing why everything—whether you like it or not—is ultimately sales.

Kelly and Brian discuss:

• 02:56 The myth that the best idea or catchiest phrase always wins
• 05:48 How the "attention economy" has changed the game
• 09:32 Why we're living in the busiest, noisiest time ever—and what that means for ensuring your message stands out
• 12:40 How Shaping Wealth evolved from an idea to a business serving the global wealth industry
• 16:23 The importance of systems over goals in sales success
• 19:27 Finding the right partnerships to complement your strengths
• 21:20 The reality check: It takes 10-12 touchpoints to drive decisions today

Connect with Kelly Waltrich: 

• LinkedIn: Kelly Waltrich
• LinkedIn: Intention.ly
• X: Intention.ly
• Instagram: Intention.ly

Connect with Brian Portnoy:

• LinkedIn: Brian Portnoy
• X: Shaping Wealth 

About Our Guest: 

Brian is one of the world’s leading experts on the psychology of money.  He has written multiple bestselling books, including The Geometry of Wealth, and has 20+ years of experience as an investor and educator in the hedge fund and mutual fund industries.  He is a CFA Charterholder and earned a PhD at the University of Chicago. 

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Are you making the biggest mistake in your business by failing to scale strategically?

Kelly Waltrich sits down with Randy Lambert and Jason Mirabella, the visionaries behind Intention.ly’s recently launched Deliver Advice operating system, to discuss how RIAs and fintech firms can overcome growth challenges, optimize operations, and build thriving businesses.

With decades of leadership experience—Randy as former President of Orion and Jason as a strategic operations expert—the duo shares how to implement the Deliver Advice framework to scale human capital, improve customer experience, and avoid common leadership pitfalls.

Kelly, Randy, and Jason discuss:

03:29 - What is Deliver Advice? The framework for scaling RIAs and fintech firms
05:08 - The three core pillars of a thriving firm: methodology, roadmaps, and human capital
08:17 - How RIAs can maximize their tech stack and operational efficiency
09:01 - The biggest pain points RIAs face when scaling
10:29 - Why what got you to $1B AUM won't get you to $10B
12:12 - The #1 mistake leaders make when rolling out new initiatives
15:33 - How to get buy-in from your team and avoid top-down failures
16:45 - The right way to lead up, down, and across your organization
21:55 - Why Deliver Advice is EOS for financial services—with a tactical twist
25:08 - Super Bowl prediction: Will the Eagles fly?

Connect with Kelly Waltrich: 

• LinkedIn: Kelly Waltrich
• LinkedIn: Intention.ly
• X: Intention.ly
• Instagram: Intention.ly

Connect with Randy Lambert: 

• LinkedIn: Randy Lambert 

Connect with Jason Mirabella: 

• LinkedIn: Jason Mirabella 

About Our Guest: 

Randy Lambert is EVP of RIA Solutions at Intention.ly, bringing over three decades of experience building and scaling RIA and WealthTech platforms. As a former executive at Orion, he played a pivotal role in growing the firm's AUM from $85 million to $70 billion and scaling their WealthTech platform to $4 trillion in AUA. Randy specializes in optimizing support models, enhancing client experience, reducing operational friction, and building high-performing teams. 

Jason Mirabella is the Platform Architect at Intention.ly, bringing over 24 years of experience in financial services with a deep focus on operational leadership, platform design, and wealth management. As the former COO of WealthSource Partners, he led strategic operations for a firm managing over $2 billion in AUM. 

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Are you making the biggest mistake in your business by trying to do everything yourself?

In this episode of Don't Do That, host Kelly Waltrich sits down with fintech legend Joel Bruckenstein to discuss the evolution of technology in wealth management, the role of AI, and the critical mistakes advisors make when building their tech stacks.

With over 21 years at the helm of the T3 Technology Conference and decades advising firms on technology adoption, Joel shares his insider perspective on the rapid advancements in AI, cybersecurity, and operational efficiency.

Kelly and Joel discuss:

03:54 The transformation of wealth tech: Then vs. Now
05:09 The essential tech stack every advisory firm needs
06:22 The biggest mistake advisors make in running their firms
09:08 Why failing fast is key to tech success
12:04 How AI is reshaping the advisor’s role
13:08 The future of AI-powered investment management
16:31 The opportunities (and risks) of AI adoption
18:12 How advisors can stay ahead by networking and learning
20:45 The must-attend event for fintech professionals: T3 Conference 2025

Connect with Kelly Waltrich: 

• LinkedIn: Kelly Waltrich
• LinkedIn: Intention.ly
• X: Intention.ly
• Instagram: Intention.ly

Connect with Joel Bruckenstein: 

• LinkedIn: Joel Bruckenstein 
• X: Joel Bruckenstein 
• Register: T3 Technology Conference 2025 
• Website: T3 Technology Tools for Today 

About Our Guest: 

Joel Bruckenstein is a leading authority on fintech and practice management for financial advisors. As the founder of T3 Technology Hub and producer of the T3 Technology Conference, Joel has spent over two decades shaping the conversation around technology adoption in wealth management.

A respected consultant, author, and speaker, Joel has advised firms on optimizing their technology stacks, cybersecurity, and operational efficiencies. His annual T3 Advisor Software Survey serves as a key industry benchmark, helping advisors navigate the rapidly evolving fintech landscape.

Through his work, Joel has been instrumental in driving innovation and helping firms harness technology to enhance client experiences and scale their businesses.

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Are you scrambling to keep pace with the AI revolution?

Kelly Waltrich sits down with Eric Clarke, a renowned influence in the financial services arena, to explore how AI is poised to transform the advisor-client journey. 

Eric shares insights from his adventures, from sitting on multiple boards to advising companies on leveraging technology for growth. With AI still in its first inning, its potential to personalize client communication and scale advisory services is immense.

Kelly and Eric discuss: 

• 04:08 The untapped potential of AI in the advisor-client journey
• 05:40 How Eric is staying on the AI cutting edge
• 10:31 Creative ways firms are starting to use AI 
• 12:04 Why AI is shifting from back-office to front-office applications 
• 12:58 What firms should look for in an AI analyst 
• 18:50 How advisors can start leveraging AI today
• 20:19 Final advice: Don't let AI pass you by
• And more

Connect with Kelly Waltrich: 

• LinkedIn: Kelly Waltrich
• LinkedIn: Intention.ly
• X: Intention.ly
• Instagram: Intention.ly

Connect with Eric Clarke: 

• LinkedIn: Eric Clarke

About Our Guest: 

Eric Clarke is the founding CEO of Orion Advisor Tech, launching the firm in 1999 to provide portfolio accounting software to help independent financial advisors scale their businesses. Eric retired as Orion’s CEO in 2023 and continues to serve as an active member of the Board of Directors. 

Over Eric’s nearly 25 years of leadership, the firm grew and evolved into Orion Advisor Solutions - a premier provider of wealthtech solutions for fiduciary advisors. Today, Orion supports over five million technology accounts and thousands of independent advisory firms with an integrated suite of fully connected, disruptive technology and investment solutions on an open architecture platform.

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Do you really know what your clients are looking for? Kelly Waltrich and H. Adam Holt, CEO and Founder of Asset-Map Holdings, explore the often overlooked gaps between what clients want and what advisors deliver. Adam offers candid insights from his transformation as a “recovering advisor,” emphasizing the critical need to address real client pain … 

 Read More Read More

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Welcome to the Don’t Do That podcast, where we flip the script on financial and business advice. Instead of another playbook on what works, we’re diving into the don’ts—the missteps, pitfalls, and hard lessons that every professional wishes they could’ve avoided. If you’ve ever wondered about the challenges behind polished success stories, this is your backstage pass. 

Let’s learn from what went wrong, so we can get it right.

Join host Kelly Waltrich, CEO and Co-founder of Intention.ly as she uncovers the secrets behind impactful growth strategies, explores building top-tier marketing teams, and challenges outdated agency practices for fintech companies eyeing transformative progress.

Top takeaways: 

• What inspired Kelly’s diverse career path and thse creation of Intention.ly
• How do unique team dynamics and culture play a role in Intention.ly’s success
• What is Intention.ly’s innovative approach to combining consulting with strategic execution
• How does marketing translate into revenue, and why is it important to turn strategy into actionable results
• How are technology and innovation shaping Intention.ly’s services, particularly with the Advisor Brand Builder tool
• And more

Connect with Kelly Waltrich: 

• LinkedIn: Kelly Waltrich
• LinkedIn: Intention.ly
• X: Intention.ly
• Instagram: Intention.ly

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Have questions or ready to start your next marketing campaign? Contact us: https://intention.ly/contact-us/