Episodes

  • How Advisors Can Beat the Biggest Retirement Risk with Erik Brenner

    How Advisors Can Beat the Biggest Retirement Risk with Erik Brenner
    Apr 21 2026
    Episode 141: This week, Kyle Van Pelt talks with Erik Brenner, CEO, President, and Founding Partner at Hilltop Wealth and Tax Solutions. With more than 30 years of experience, Erik has assisted thousands of individuals in integrating retirement, tax, and estate strategies. At Hilltop, he blends leadership and client advisory responsibilities, shaping the firm's future vision and strategies while providing personalized financial guidance to select clients. Erik talks with Kyle about what happens when advisory firms stop treating tax and wealth management as separate conversations and start thinking holistically. He discusses the strategic decisions that helped transform Hilltop, including integrating in-house tax services, rethinking the client experience, and doubling down on education-driven growth. Erik also shares how to run great seminars and use technology to keep up with business complexities. In this episode: (00:00) - Intro (01:06) - Erik's money moment (03:30) - Hilltop's one-stop model: Integration of tax and wealth management (07:13) - How Hilltop manages large wealth with tax problems (09:35) - How the SECURE 2.0 Act impacts generational wealth (16:37) - Using seminars as a modern growth engine (20:28) - What makes a 5-star seminar experience (23:39) - Managing tech across multiple business lines (25:29) - Navigating the transition from being an advisor to a CEO (27:33) - Erik's outlook on the future of the financial industry (29:03) - Erik's Milemarker Minute Key Takeaways Don't outsource critical expertise that directly affects client outcomes. If a core part of your value—like tax strategy—is outside your control, alignment becomes difficult. Integrate tax and wealth management to deliver truly holistic advice. When strategy and execution live under one roof, decisions become more coordinated, proactive, and impactful for clients. For many retirees, taxes are their biggest expense. Plan accordingly. Investment returns matter, but unmanaged tax exposure can quietly erode wealth faster than most clients realize. Education builds trust faster than selling ever will. Whether it's seminars or client meetings, people lean in when they feel informed, not when they feel pitched. Teach first, and the business follows. Quotes "For most of our clients who are into retirement, taxes are their number one expense." ~ Erik Brenner "If you don't know the right questions to ask about how laws are changing, even the most powerful AI won't be able to help you." ~ Erik Brenner "Marketing is about getting the ball rolling. You want to get that ball rolling, but you do not want the snowball to melt." ~ Eric Brenner Links Erik Brenner on LinkedIn Hilltop Wealth and Tax Solutions Holistiplan The Personal CFO Revolution Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube 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.
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    33 mins
  • Serving Clients in Life's Most Difficult Moments with Anne McPhail

    Serving Clients in Life's Most Difficult Moments with Anne McPhail
    Apr 14 2026
    Episode 140: This week, Kyle Van Pelt talks with Anne McPhail, Managing Director at Novare Capital Management. With more than 30 years of experience across corporate banking and wealth management, Anne brings deep experience in wealth management, with a focus on guiding clients through major life transitions and building advisory relationships rooted in trust, empathy, and long-term perspective. Anne talks with Kyle about what it truly means to serve clients through life's most important and often most difficult moments. She shares how genuine empathy and thoughtful financial strategy come together to create meaningful client relationships, how leading advisory firms deliver a consistent, high-touch experience at scale, and how Novare develops the next generation of advisors without compromising trust. In this episode: (00:00) - Intro (01:43) - Anne's money moment (04:18) - Novare's life transition playbook (07:13) - Scaling personalized service across the firm (09:06) - Anne's advice for young wealth professionals (11:19) - Developing the next generation of advisors (18:28) - Staying current in a changing industry (21:17) - Integrating planning into every aspect of clients’ lives (25:00) - Building trust that lasts through life's uncertainties (25:56) - Philanthropy, community, and relationship building (30:37) - Anne's outlook on the future of financial services (33:50) - Anne's Milemarker Minute Key Takeaways Lead with empathy before expertise. When clients face major life transitions—loss, divorce, uncertainty—they don't want spreadsheets. They want reassurance. Great leaders and advisors meet people where they are emotionally before guiding them analytically. Build systems that deliver consistent excellence. Scaling a high-touch experience isn't about doing more. It's about doing things intentionally. Clear processes, defined roles, and shared standards create consistency across every client interaction. Pair experience with a fresh perspective. Blending seasoned professionals with next-gen talent creates both trust and innovation. It allows firms to evolve without losing credibility. The value isn't in the plan, but in the conversation. Financial plans change. Life changes. What matters most is the ongoing dialogue and adaptability, not the static document. Quotes "You cannot manage a client or a family's money if you do not know their goals and objectives." ~ Anne McPhail "The mistake that a lot of firms make is meeting with a client who's lost their spouse, and the first thing they do is prepare a financial plan and give a Monte Carlo analysis. That's completely overwhelming to someone." ~ Anne McPhail "When you're trying to develop centers of influence, look for people who are about your age and stage of life who are trying to build their careers alongside you." ~ Anne McPhail Links Anne McPhail on LinkedIn Novare Capital Management Wells Fargo eMoney Advisor Charles Schwab Charlotte Family Housing Good Friends Charlotte Arts+ Theo of Golden Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube 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.
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    37 mins
  • Best Of: The Hidden Cost of Fragmented Data with Kailash Duraiswami

    Best Of: The Hidden Cost of Fragmented Data with Kailash Duraiswami
    Apr 7 2026
    Episode 139: Kailash Duraiswami is the Chief Technology Officer at Milemarker, where he leads the development of data infrastructure and AI-powered solutions for modern advisory firms. With a unique blend of financial expertise and deep technical knowledge, Kailash brings his passion for innovation, data strategy, and scalable technology to help wealth management firms thrive in a multi-platform world. In this episode, Kyle Van Pelt talks with Kailash about his unconventional path from launching an RIA straight out of college to building tech that transformed data operations for financial firms. They unpack the challenges firms face with fragmented data, the importance of centralized infrastructure, and how AI will reshape wealth management. They discuss why firms need to reclaim ownership of their data, how to avoid becoming an “accidental CTO,” and how Milemarker is building scalable, simplified tech solutions for advisors navigating a multi-platform, AI-enabled world. In this episode: (00:00) - Intro (03:17) - Kailash's money moment (08:20) - What is Pantenix? (11:34) - The value of a data warehouse (13:55) - Kailash's thoughts on cloud-based infrastructure (15:40) - The importance of data platforms (19:53) - Why becoming a CTO should be intentional (23:54) - AI in wealth management (26:10) - The advantage of building your own language models (33:15) - Why CTOs in RIAs need to understand wealth management (37:26) - Why all-in-one platforms limit user experiences (40:27) - Kailash's Milemarker Minute Key Takeaways Centralize your data to maximize AI and operational efficiency. Without consolidating your firm’s data into a single, accessible environment, it’s nearly impossible to generate meaningful insights or leverage AI effectively. Fragmented data limits your ability to scale and innovate. You don’t have to become an “accidental CTO”. Many firm leaders end up spending too much time wrestling with tech. Outsourcing specialized functions—like data architecture and infrastructure—can free up your time to focus on clients and growth, while still driving innovation. Owning your data is not the same as using cloud-based tools. Just because your systems are in the cloud doesn’t mean you own your data. True ownership means having control over how and where your data is stored, accessed, and used to make decisions. AI is only as smart as the data it has access to. For AI to deliver meaningful outcomes—like intelligent agents or predictive analytics—it needs clean, well-structured, and centralized data. Start with solid infrastructure before diving into advanced AI capabilities. Quotes "What we're doing here, as a help to your technology footprint, is enabling you to see and understand your business in ways you've never done before. And that requires very sophisticated technology." ~ Kailash Duraiswami "You must have your data in one place to really make use of AI because the conclusions that the model can make or the recommendations are all subject to what data is presented to it." ~ Kailash Duraiswami "The biggest thing we are making here is building a tool that is advisor-centric and executive-centric. And that means simplicity. Above all, the boldness of what we have here is to do less in an excellent way." ~ Kailash Duraiswami Links Kailash Duraiswami on LinkedIn Orion Advisor Solutions Black Diamond Tamarac Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube 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.
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    43 mins
  • How to Build Deep Client Relationships at Scale with Michael Vedders

    How to Build Deep Client Relationships at Scale with Michael Vedders
    Mar 31 2026
    Episode 138: This week, Kyle Van Pelt talks with Michael Vedders, Senior Vice President of Marketing & Enterprise Resources at NorthRock Partners. In his role, Michael is responsible for extending NorthRock's reach and reputation. With more than a decade of experience in marketing and leading complex organizational projects, Michael has helped build teams, launch major branding initiatives, produce compelling creative, develop multi-channel planning, and use insights to inform strategy. Michael talks with Kyle about how wealth management firms can build deep client relationships at scale. He discusses the importance of storytelling in creating a strong brand narrative, how NorthRock's personal office business model works, and why the future belongs to firms that use data and automation to serve more people and build deeper human connections. In this episode: (00:00) - Intro (02:38) - Michael's money moment (04:58) - Michael's frustration with traditional wealth management (07:24) - What marketing really means in wealth management (10:02) - How to build trust and deeper client relationships (12:48) - The "quarterback" model of financial advice (16:42) - How NorthRock manages deep relationships at scale (21:52) - NorthRock's personal office business model (22:54) - Michael's outlook on the future of financial advice (29:03) - Redefining performance beyond returns (30:57) - Michael's Milemarker Minute Key Takeaways Don't rush to promote. Get your story right first. It's tempting to jump straight into marketing tactics, but without a clear, compelling story, even the best campaigns fall flat. Take the time to define what truly sets you apart before amplifying your message. If you want deeper client relationships, create space for them. You can't force meaningful connections, but you can design for them. Offload technical tasks to specialists so advisors can focus on what matters most. Use technology to create time, not just efficiency. AI and automation aren't the end goal. The real opportunity is what you do with the time they create. The best firms will reinvest that time into deeper relationships and better service. The future belongs to firms that balance tech and humanity. Efficiency through data and automation is table stakes. The real edge comes from using that efficiency to deepen human connection, not replace it. Quotes "Marketing is the privilege of telling the story, the story of your firm and what differentiates you. You can spend a lot of money and generate a lot of activity without results if you don't provide a clear story for people first." ~ Michael Vedders "Deep relationships lead to better advice." ~ Michael Vedders "The future of our industry belongs to those who can create efficiencies and space through data and automation, and then use that space to serve people more effectively and deepen relationships." ~ Michael Vedders Links Michael Vedders on LinkedIn NorthRock Partners Think Again Switch Unreasonable Hospitality Love Does The Ideal Team Player Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube 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.
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    34 mins
  • How Financial Advisors Can Turn Messy Data into Actionable Results with Verity Larsen

    How Financial Advisors Can Turn Messy Data into Actionable Results with Verity Larsen
    Mar 24 2026
    Episode 137: This week, Kyle Van Pelt talks with Verity Larsen, Founder & CEO at Versoft Consulting. Versoft partners with RIAs to help navigate complex technology decisions, system conversions, and data strategy. Verity talks with Kyle about the realities behind data lakes in wealth management and why maintaining clean, accurate data is harder than it looks for RIAs. From the myth of "clean data" to the hidden costs of data lakes, Verity shares a behind-the-scenes look at why so many firms struggle to turn data into actionable insights. She also explores the limitations of AI, the operational disconnects that quietly slow firms down, and what it truly takes to make data work for growth and better decision-making. In this episode: (00:00) - Intro (02:00) - Verity's money moment (04:33) - The challenge of validating data in system conversions (08:40) - What it takes for an RIA to maintain clean data (13:28) - The disconnect between management and staff workflow (16:43) - Common reasons people hire Versoft (20:53) - How people can make the most of their current technology (26:27) - Why systems calculate the same metrics differently (32:01) - The limits of AI in data and system management (37:43) - The truth about data lakes: adoption vs. actual results (40:11) - What firms should be doing with their data lakes (42:28) - The next best step after centralizing data (44:47) - Verity's Milemarker Minute Key Takeaways Start with the outcome, not the infrastructure. It's tempting to jump on trends like data lakes or AI, but without a clear use case, you'll end up with expensive systems that don't deliver value. Your data isn't as clean as you think. Many firms assume their data is accurate until they attempt to migrate or validate it. Taking the time to clean and fully understand data upfront can prevent months or even years of frustration down the line. Data consolidation without a plan is a dead end. Bringing all your data into one place is only step one. The real value comes from how you use it, whether that's improving client experiences or driving better business decisions. Growth comes from visibility. When your data is structured and accessible, it becomes a powerful tool for identifying opportunities, improving profitability, and intentionally scaling your business. Quotes "A lot of people have been talking about collecting their data into a single source. They start with that initiative, but they don't actually think about what they want to do with that information once it's all together." ~ Verity Larsen "Most people assume that their data is clean. So, they think that validating that data is going to be easy, and it's not." ~ Verity Larsen "If you are looking to change systems or expand data warehousing services, make sure you scrub your data in advance so your source data is accurate, you know what you have, and you know what problems to expect if that data is moved into a different system." ~ Verity Larsen Links Verity Larsen on LinkedIn Versoft Consulting SS&C Advent Joshua Brown Ritholtz Wealth Management Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube 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.
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    47 mins
  • Bringing Consumer Fintech and Wealth Management Together with Nicole McMullin

    Bringing Consumer Fintech and Wealth Management Together with Nicole McMullin
    Mar 17 2026
    Episode 136: This week, Kyle Van Pelt talks with Nicole McMullin, Senior Vice President of Product at Wealth.com. Nicole is a seasoned product leader with a proven track record of building and scaling high-performing product organizations. She brings deep experience in product strategy, cross-functional leadership, and translates customer needs into meaningful outcomes. Nicole talks with Kyle about the intersection of consumer fintech and advisory technology and how modern fintech principles can transform the advisor-client experience. She explores how new tools, AI workflows, and integrated platforms are helping advisors move away from manual processes and toward more proactive, emotionally intelligent conversations with clients. In this episode: (00:00) - Intro (03:09) - Nicole's money moment (09:42) - What advisory firms can learn from consumer fintech (12:58) - Nicole's 'aha' moment at Wealth.com (13:37) - Wealth's new tax planning strategy (14:44) - Addressing fragmentation in wealth management (16:26) - What attracted Nicole to join Wealth.com (21:46) - How advisors should evaluate new technology (23:33) - Nicole's outlook on the future of wealth management (27:56) - How Wealth.com provides the best wealth management experience (30:16) - Nicole's Milemarker Minute Key Takeaways Financial planning, estate strategies, and tax modeling can be incredibly complex. But the most effective tools translate that complexity into something clients immediately understand. Great financial advice is still deeply human. The role of technology is to support that relationship by translating emotional client conversations into actionable insights, strategies, and next steps in real time. Many advisors give excellent recommendations. But clients don't always follow through. Technology that helps advisors turn recommendations into immediate actions can dramatically improve client outcomes. The biggest challenge in advisor technology isn't capability, it's fragmentation. Platforms that consolidate data from multiple tools into one cohesive view of a client's financial life create far more value. Quotes "Advisors really are that emotional support system, and the product needs to empower clients and advisors to have that conversation." ~ Nicole McMullin "Platforms like Wealth.com have the ability to almost instantaneously take the emotional conversation, translate it, and allow the advisor to show how it may change their plan, investment strategy, and tax strategy." ~ Nicole McMullin "Allowing advisors to have that magical moment of taking a person where they are today and immediately translating that and showing them the output of where they're going can go a long way in empowering advisors." ~ Nicole McMullin Links Nicole McMullin on LinkedIn Wealth.com Dan Bolton Square Nitrogen Jump AI Zocks Charles Schwab Goldman Sachs Tomorrow, and Tomorrow, and Tomorrow Cash App Wealthfront Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube 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.
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    35 mins
  • Relentless, Relevant, and Ready: Orion Ascent Recap with Jessica Perez

    Relentless, Relevant, and Ready: Orion Ascent Recap with Jessica Perez
    Mar 10 2026
    Episode 135: This week, Kyle Van Pelt talks with Jessica Perez, VP of Growth at Milemarker. Jessica brings a boots-on-the-ground perspective to the wealth management technology space, working directly with advisory firms to help them unlock the full potential of their data. Kyle and Jessica recap key lessons from the Orion Ascent conference, where the central theme was “Relentless”—a mindset focused on continuous improvement across technology, client experience, and firm operations. They discuss how advisors can avoid the overwhelm that often follows large industry events and instead identify one or two meaningful priorities to pursue. Jessica also shares her perspective on evaluating technology partners, embracing innovation like AI without chasing every trend, and focusing on the changes that truly move an advisory firm forward. In this episode: (00:00) - Intro (01:28) - Orion Ascent recap (03:15) - How advisors can apply a relentless mindset without getting distracted (07:29) - The "AI frenzy" and improving client experience through smarter technology (10:29) - How AI conversations are shaping advisor technology strategy (13:24) - From tinkering to transformation (15:02) - Evaluating whether technology vendors are true partners (20:11) - Why data sharing and integration matter more than ever (25:08) - Turning conference inspiration into real firm improvements (38:43) - Jessica's Milemarker Minute Key Takeaways Be ruthless about technology partners that don’t truly help your business. If a platform doesn’t share data well, integrate with your ecosystem, or actively help improve your client experience, it’s worth reevaluating that relationship—even if switching tools feels painful. Technology vendors should function as partners in growth, not just software providers.  Don’t chase every new idea after a conference—pick a few and pursue them relentlessly. Industry events flood advisors with dozens of new tools and ideas, but trying to implement everything leads to distraction. Instead, identify one to three ideas that meaningfully improve your firm and focus on executing those relentlessly throughout the year.  “Relentless” improvement is more about mindset than technology. The real takeaway from Orion Ascent wasn’t just AI or new fintech announcements—it was the mindset of continuous improvement. Firms that consistently ask how they can serve clients better, improve workflows, and elevate their teams are the ones that ultimately win.  Quotes “Relentless means find a theme, find a thing that matters that you can relentlessly pursue.” ~ Jessica Perez “If you are not actively in play right now, thinking about how your firm can handle AI to serve your clients, you're gonna have a lot of problems.” ~ Jessica Perez Links Jessica on LinkedIn Orion Ascent Jordan Hutchison Chip Kispert Future Proof T3 The Challenger Sale by Matthew Dixon The Activator Advantage by Matthew Dixon Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube 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.
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    Not Yet Known
  • Building Resilient Firms in the Age of AI with Chip Kispert

    Building Resilient Firms in the Age of AI with Chip Kispert
    Mar 3 2026
    Episode 134: This week, Kyle Van Pelt talks with Chip Kispert, Founder & Managing Partner at Beacon Strategies. Chip has spent decades building and leading one of the country’s most trusted wealth management partners, helping shape its national footprint through intentional M&A, strong partner alignment, and disciplined operational systems. His career reflects a deep commitment to sustainable growth, advisor development, and long-term enterprise value creation. Kyle and Chip explore what it takes to build durable advisory businesses while embracing innovation. They discuss the power of structured peer roundtables, how firms can move beyond legacy technology assumptions, and why operational rigor becomes more important as firms grow. The conversation also dives into AI adoption—distinguishing native versus enabled tools, addressing internal fear, and establishing formal AI policies—highlighting how thoughtful leadership can turn disruption into long-term enterprise value. In this episode: (00:00) - Intro (01:45) - Chip's money moment (04:23) - What Beacon Strategies does and who it serves (08:03) - Why structured roundtables outperform traditional conferences (11:39) - Why firms are reassessing legacy technology providers (15:19) - Native AI vs. AI-enabled tools (17:27) - Managing fear and uncertainty around AI (22:48) - Avoiding AI overload and creating a formal policy (27:29) - Introducing the Beacon Provider Network (BPN) (31:20) - One area financial services must improve (35:08) - Chip's Milemarker Minute Key Takeaways Don’t adopt AI casually—govern it deliberately. Experimentation is fine, but firms need a formal AI policy to reduce risk, clarify expectations, and prevent tool sprawl. Thoughtful governance creates confidence internally and credibility externally. Distinguish between “native AI” and “AI-enabled” tools. Not all AI is created equal. Leaders must understand whether AI is foundational to a product or simply layered on as a feature. That distinction impacts scalability, data security, and long-term strategic fit. Peer collaboration beats passive learning. Structured roundtables and curated peer groups often produce more actionable insight than traditional conferences. Real progress happens when leaders openly share what’s actually working—and what isn’t. Operational discipline becomes more important as innovation accelerates. As firms scale and technology multiplies, clarity around standards, vendor evaluation, and internal processes becomes a competitive advantage. Growth without structure creates fragility. Quotes "Most firms don't have any AI policy. They need to have an AI vision and an AI policy to lay out their plans and the information they need, so they know their data is protected. They need to have their guidelines and guardrails, which drive their decisions on how they interact with firms." ~ Chip Kispert "There's a lot of talk about AI, but a true understanding of it is not rich. It's not deep. So, it would be absolutely valuable for the wealth space to really have some AI learning. Everybody can say large language model, but truly understanding it is another world." ~ Chip Kispert "Data management is the foundation of everything. You can have great AI or rules-based engines, but if the data is not good, it doesn't mean anything. All the pretty stuff, the shiny metal lures don't have that much integrity, or their integrity gets questioned by the quality of the data." ~ Chip Kispert Links Chip Kispert on LinkedIn Beacon Strategies Fidelity Investments Beacon Provider Network Connect with our hosts Milemarker.co Kyle on LinkedIn Jud on LinkedIn Subscribe and stay in touch Apple Podcasts Spotify YouTube Produce game-changing content with Turncast Turncast helps your company grow by producing top-quality content and fostering transformative conversations. Learn more at Turncast.com.
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    38 mins