The Capital CEO

Jen Conkey
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Capital CEO features candid conversations with entrepreneurs who have built six-, seven-, and eight-figure businesses by solving real problems and learning how to monetize them. Host Jen Conkey explores the journey behind the growth—what worked, what changed, where profits go, and how successful founders think about capital, opportunity, and what comes next.

  1. 19h ago

    EP28 | Stop Selling. Start Pitching: How to Get People to Say Yes | Forbes Riley

    What if the fastest way to grow your influence is to stop “selling”, and learn how to make people genuinely want to say yes? In this episode of THE Capital CEO, Jen Conkey sits down with Forbes Riley, award-winning TV host, bestselling author, entrepreneur, and communication expert known worldwide as the “Queen of Pitch,” to break down the psychology, language, and presence behind a pitch that actually moves people. Forbes shares how a childhood marked by difficulty communicating ultimately shaped a career built around being heard. After decades in television, live selling, and direct response, including 197 infomercials and more than $2.5 billion in product sales, she has learned that the strongest pitch is not about talking more. It is about understanding the person in front of you, creating curiosity, and making your value immediately relevant to them. Jen and Forbes unpack the difference between pitching and selling, Forbes’s “question flip,” why “What do you do?” should really be heard as “What can you do for me?”, and the principle she calls “less words, more impact.” They also explore body language, strategic word choice, NLP and embedded commands, one-to-many communication, money beliefs, family, legacy, and what it means to build success without losing sight of the people who matter most. KEY TOPICS • Why pitching is different from selling • How to create a “yes, tell me more” response • Turning “What do you do?” into “What can you do for me?” • Forbes Riley’s “less words, more impact” approach • The question flip and understanding what people actually want • Why every word matters when you communicate your value • Body language, presence, and reading the person in front of you • NLP, embedded commands, and the psychology of influence • Selling one-to-many from stages, media, and live presentations • Breaking limiting beliefs around money and success • Pitch Secrets A to Z and the lessons behind Forbes’s pitching framework • Raising entrepreneurial kids while keeping family first • Using active income to build assets, cash flow, and long-term legacy • How pitching applies to investors, partnerships, relationships, and everyday life ABOUT FORBES RILEY Forbes Riley is an award-winning TV host, bestselling author, entrepreneur, inventor, and communication expert known worldwide as the “Queen of Pitch.” Across a decades-long career in television and direct response, she has hosted 197 infomercials and helped generate more than $2.5 billion in product sales. She is the creator of SpinGym, an inductee into the National Fitness Hall of Fame, and a recognized authority on pitching, sales psychology, performance, and communication. Her latest book, Pitch Secrets A to Z, teaches practical strategies for building confidence, communicating value, creating influence, and getting more people to say yes. CONNECT WITH FORBES RILEY Website: https://forbesriley.com/ Instagram: https://www.instagram.com/forbes_riley/ Facebook: https://www.facebook.com/ForbesRileyFanPage YouTube: https://www.youtube.com/@ForbesRileyOfficial LinkedIn: https://www.linkedin.com/in/forbesriley/ Pitch Secrets A to Z: https://pitchsecretsbook.com/ Free Sunday Pitch Training: https://www.pitchsecretstraining.com/ #TheCapitalCEO #ForbesRiley #Pitching #SalesPsychology #Entrepreneurship

  2. 4d ago

    EP27 | How I Allocate Capital: My Actual Portfolio and Why

    Building a successful business and knowing where to invest its profits require two very different skill sets. As an operator, you're rewarded for making things work. As a capital allocator, success often comes from knowing when to step back, manage risk, or walk away. In this solo episode of THE Capital CEO, Jen Conkey opens up the Capital Titans portfolio and explains the reasoning behind its allocation: 62% housing, 25% alternative debt, 7% oil and gas, 5% hospitality, and 1% self-storage. More importantly, she shares why each category has earned its place, and why some positions are deliberately small. Jen breaks down how she evaluates cash flow versus long-term growth, the financing risks that immediately disqualify a deal, and why the quality of an operator matters as much as the opportunity itself. She also explains her personal framework for dividing income between living expenses, investments, and reserves, while addressing the practical challenges of building a diversified portfolio over time. The central question isn't simply whether an investment is a good deal. It's whether that investment is the right place for your next dollar, given everything you already own. KEY TOPICS • The difference between thinking like an operator and thinking like a capital allocator • Jen's actual Capital Titans portfolio allocation and the reasoning behind each position • Why housing and alternative debt account for the largest portions of her portfolio • How position sizing reflects conviction, risk, and economic sensitivity • Cash flow now versus potential growth later—and why timing matters • Why Jen avoids variable-rate financing and looks for a debt service coverage ratio of at least 1.3 • How she evaluates operators, identifies risks, and decides which deals to reject • Her 70/20/10 personal income framework and the importance of adequate reserves • Liquidity, investment minimums, and the realities of building an allocation over several years • A practical exercise to understand where your wealth is currently concentrated ABOUT JEN CONKEY Jen Conkey is an entrepreneur and investor who has built three companies to seven, eight, and nine figures and deployed capital into a nine-figure commercial real estate portfolio. Through THE Capital CEO, she focuses on the mechanics of scaling businesses, allocating capital strategically, and turning business success into long-term ownership and wealth. JOIN JEN’S PRIORITY ACCESS LIST Get access to rooms, tools, details, and opportunities Jen does not share publicly: https://thecapitalceo.com/connect SCHEDULE A CONVERSATION WITH JEN Interested in exploring which investment opportunities may fit your goals, resources, risk tolerance, and timeline? Use the form below to start a conversation with Jen and her team: https://api.leadconnectorhq.com/widget/form/ZzogXFed0H6SfqOXPnqp ABOUT THE CAPITAL CEO THE Capital CEO features candid conversations with entrepreneurs who have built six-, seven-, and eight-figure businesses by solving real problems and learning how to monetize them. Host Jen Conkey explores the journey behind the growth, where successful founders invest their profits, and how they think about capital, opportunity, and what comes next. This episode is for educational and informational purposes only and is not financial, tax, legal, or investment advice. #TheCapitalCEO #CapitalAllocation #WealthBuilding #RealEstateInvesting #Entrepreneurship

  3. Oct 2

    EP26 | Lead Yourself, Build Bigger: Identity, Culture & Building a Business Your Way | Melanie Ann Layer

    What if the fastest way to build something extraordinary is to stop trying to become who the market expects, and lead yourself first? In this episode of THE Capital CEO, Jen Conkey sits down with Melanie Ann Layer, Founder & CEO of Alpha Femme, to talk about self-leadership, identity, business growth, culture, intuition, team standards, and what it looks like to build a company around a way of being rather than a formula. Melanie shares the story of rebuilding her life after bankruptcy and a period of living out of her car, then creating a coaching business from that season of reinvention. She describes how Alpha Femme later grew from a deeply personal philosophy centered on self-leadership, empowerment, and possibility rather than from a conventional business plan. Jen and Melanie explore the difference between culture and cult-like dependence, why empowerment requires personal responsibility, and how a strong brand can invite people into a shared standard without asking them to lose their individuality. They also discuss building from desire instead of obligation, resisting structures that feel misaligned, knowing when a “no” is truly a no, and the importance of learning the work yourself before delegating it. KEY TOPICS • Rebuilding identity after a major personal and financial collapse • Creating a business from lived experience instead of a formula • Self-leadership as the foundation of Alpha Femme • The difference between culture and dependency • Empowerment, responsibility, and personal agency • Building a brand that does not require people to lose themselves • Why success can expand when founders stop forcing misaligned strategies • Leading from desire instead of obligation • Knowing your own operating style as a CEO • Building a business without over-structuring it • Why founders may need to do the work themselves before delegating • Hiring from a clear standard instead of hoping someone will figure it out • Authentic communication versus performance-based marketing • Staying connected to the work you actually love as the business grows ABOUT MELANIE ANN LAYER Melanie Ann Layer is the Founder & CEO of Alpha Femme. Her work focuses on self-leadership, empowerment, identity, business growth, and helping ambitious women expand what they believe is possible for themselves. After rebuilding her life and business from a period of financial hardship, she developed a coaching business and later created Alpha Femme as a brand centered on women leading themselves, owning their choices, and growing without abandoning who they are. CONNECT WITH MELANIE ANN LAYER Website & Links: https://linktr.ee/MelanieAnnLayer Instagram: https://www.instagram.com/melanieannlayer/ Alpha Femme Instagram: https://www.instagram.com/alphafemme/ Facebook: https://www.facebook.com/melanieannlayer.alphafemme LinkedIn: https://ca.linkedin.com/in/melanielayer #TheCapitalCEO #SelfLeadership #WomenInBusiness #PersonalDevelopment #Entrepreneurship

  4. Oct 1

    EP22 | Let Fear Point the Way: Scaling a Mission-Driven Franchise | Katrina Wyckoff

    What happens when a fitness business becomes more than a studio, and grows into a movement built around belonging, confidence, and community? In this episode of THE Capital CEO, Jen Conkey sits down with Katrina Wyckoff, Founder of Vertica Fitness, to talk about franchising, mission-driven growth, leadership, community, and what it takes to scale a business without losing the values that made it meaningful in the first place. Katrina shares how her background in dance and studio ownership eventually led her to pole fitness, where she saw an opportunity to create a space centered on strength, self-expression, and the belief that Every BODY Belongs. After years of building studios and navigating the pandemic, she made the decision to move into franchising so that the model, and the community behind it, could grow beyond a single location. Jen and Katrina discuss the mindset required to step into a larger vision, how to make big decisions when the path feels uncertain, and why purpose can feel very different from obligation. They also explore the franchise model, recurring membership revenue, franchisee support, brand culture, pole sport as an athletic discipline, and Katrina’s work helping expand the sport through national and international federations. KEY TOPICS • Turning a local studio into a mission-driven franchise • Building a brand around belonging, confidence, and community • Moving from obligation into purpose as a founder • Making big decisions when the vision feels bigger than you • Franchising as a model for expanding impact • Supporting franchise owners with systems, mentorship, and culture • Recurring membership revenue and additional studio revenue streams • Creating a brand that can scale without losing its identity • Pole fitness as sport, art, fitness, and self-expression • Katrina’s work with the U.S. Pole Sports Federation and POSA • Long-term vision, legacy, and building for the next generation • Why money matters in business, but cannot be the only reason for building it ABOUT KATRINA WYCKOFF Katrina Wyckoff is an entrepreneur and the Founder of Vertica Fitness, a growing pole and aerial fitness franchise built around the belief that Every BODY Belongs. Known for her strategic vision and systems-driven leadership, she works with franchise partners to build strong studios, teams, and communities while protecting the culture and mission behind the brand. Katrina also serves as President of the U.S. Pole Sports Federation and Vice President of the Pole Sports & Arts World Federation (POSA), where she is involved in advancing pole sport internationally. CONNECT WITH KATRINA WYCKOFF Vertica Fitness: https://verticafitness.com/ Franchise Information: https://www.verticafitness.com/franchise/ Instagram: https://www.instagram.com/katrinawyckoff_pole/ Vertica Fitness Instagram: https://www.instagram.com/verticafitness/ LinkedIn: https://www.linkedin.com/in/katrina-wyckoff-b4138b234 #TheCapitalCEO #Franchising #FitnessBusiness #Leadership #Entrepreneurship

  5. Oct 1

    EP24 | Build Wealth Around Your Life: Real Estate, Teams & Freedom | Ben Nelson

    What if the best business model isn’t the biggest one, but the one that gives you more time, stronger relationships, and a life you actually want to live? In this episode of THE Capital CEO, Jen Conkey sits down with Ben Nelson, Partner at Wild Oak Capital, to talk about real estate syndication, capital raising, team structure, risk, market selection, and building a business around the life you want instead of letting the business consume it. Ben shares how he moved from producing large-scale action sports events around the world into real estate and multifamily investing. After years of solving complex problems, managing teams, and building relationships in high-pressure environments, he and his partners began investing in workforce housing and eventually launched Wild Oak Capital. Jen and Ben discuss how syndication works, why relationships matter so much in real estate, how Wild Oak chooses markets outside its own backyard, and why a smaller, highly aligned team can often move faster than a large organization. They also explore the importance of setting expectations early, preparing for problems instead of assuming everything will go right, building the right people into the right roles, and staying patient when a deal does not make sense. KEY TOPICS • Transitioning from action sports and events into real estate investing • Building Wild Oak Capital around family, freedom, and long-term wealth • How real estate syndication and limited partnerships work • Raising capital and partnering with investors • Choosing markets based on opportunity, teams, and operating conditions • Why strong local property-management relationships matter • Staying patient when a deal does not pencil • Setting expectations clearly with partners and property managers • Learning from early operational mistakes • Building a lean team with complementary strengths • Preparing for problems before they happen • Solving constraints calmly instead of reacting from panic • Creating meaningful events and communities around shared values • Why experiences, relationships, and alignment can matter more than scale for its own sake ABOUT BEN NELSON Ben Nelson is a Partner at Wild Oak Capital, where he works across capital raising, investor relationships, acquisitions, and real estate operations. Before moving into real estate, Ben spent years producing action sports events and working with major brands, experiences that shaped his approach to problem-solving, project management, and relationship building. Today, he and his partners focus primarily on workforce housing and multifamily investments while building a business designed around long-term relationships, flexibility, and family. CONNECT WITH BEN NELSON Wild Oak Capital: https://www.wildoakcapital.com/ Instagram: https://www.instagram.com/wildoakcapital/ Facebook: https://www.facebook.com/WildOakCapital/ LinkedIn: https://www.linkedin.com/company/wild-oak-capital/ Note: This episode discusses real estate syndication, investing, returns, and other financial topics for educational purposes. Nothing in this episode should be considered individualized financial, legal, tax, or investment advice. All investments involve risk, and actual outcomes vary based on market conditions, execution, financing, and other factors. #TheCapitalCEO #RealEstateInvesting #CapitalRaising #Multifamily #Entrepreneurship

  6. Oct 1

    EP23 | Build a Business You Can Sell: Exit Readiness, Systems & Value | Astrid Madeleine Wyke

    What if the real exit strategy starts long before you’re ready to sell, by building a business that can stand on its own without you? In this episode of THE Capital CEO, Jen Conkey sits down with Astrid Madeleine Wyke, Co-Founder & CEO of Ledger + Legacy LLC and an exit architect, to talk about business exits, transferable assets, founder dependence, infrastructure, profitability, and what makes a company genuinely sellable. Astrid shares how her own first exit began with a disappointing valuation. After 15 years in business, she discovered that the biggest obstacle wasn’t revenue, it was how dependent the company still was on her. That experience forced her to rebuild the business around systems, delegation, decision-making, team structure, and profitability until it could operate without her day-to-day involvement. Jen and Astrid discuss why founders often mistake surface-level problems for the real constraint, how capacity blocks can stall growth, and why the intellectual property inside a founder’s head has to be unpacked into repeatable systems. They also explore self-managing teams, data dashboards, financial metrics, profit margin, buyer readiness, and why building for exit can make a business stronger even if the founder never plans to sell. KEY TOPICS • What makes a business a sellable, transferable asset • Founder dependence and key-person risk • Turning founder knowledge into repeatable intellectual property • Why delegation often fails without enough detail • Building infrastructure that can replace founder involvement • Front-end problems versus back-end operational bottlenecks • Scalability audits and exit-readiness audits • Profit margin, payroll, and financial efficiency • Building self-managing teams • Using dashboards and data to make stronger business decisions • Preparing financials and systems for buyer due diligence • Why an exit can mean selling, or simply replacing yourself as CEO • Building a business that can continue operating during unexpected life events • Why exit planning can begin years before a transaction ABOUT ASTRID MADELEINE WYKE Astrid Madeleine Wyke is the Co-Founder & CEO of Ledger + Legacy LLC and an exit architect who helps founders build businesses that can operate, scale, and retain value without depending on the founder for every decision. After restructuring and selling her own company, she began applying the same principles to other businesses through exit architecture, infrastructure design, scalability strategy, and fractional executive work. CONNECT WITH ASTRID MADELEINE WYKE Website: https://astridmadeleinewyke.carrd.co/ Instagram: https://www.instagram.com/astridmadeleinewyke/ Book a Call: https://calendly.com/astrid-second-chair/connect-with-astrid?month=2026-10 #TheCapitalCEO #ExitStrategy #BusinessSystems #BusinessGrowth #Entrepreneurship

  7. Oct 1

    EP21 | Make Your Money Work for You: Simple Investing for Long-Term Wealth | Kristen Wonch

    What if building wealth had less to do with chasing the next hot investment, and more to do with creating a simple system you can understand and maintain? In this episode of THE Capital CEO, Jen Conkey sits down with Kristen Wonch, Founder of Compounding Queens and a wealth coach, to talk about investing, diversification, financial education, risk, and the value of understanding how a long-term portfolio works. Kristen shares how her background in commodities trading and finance did not automatically translate into personal wealth. Despite working in the industry and earning well, she found herself overspending, carrying debt, and not investing consistently. That experience eventually led her to rethink the way she approached money and build a business focused on helping women understand investing for themselves. Jen and Kristen discuss diversified portfolios, ETFs, growth versus dividend-paying stocks, long-term investing, financial-advisor fees, and why understanding risk matters before putting money into any asset. Kristen also shares one of her early investing mistakes, using leveraged options and watching a large gain disappear quickly, and explains why her approach today emphasizes simplicity, diversification, and long-term consistency over high-risk trading. KEY TOPICS • Why earning a high income does not automatically create wealth • Building financial confidence through education • Diversification across investments and asset classes • ETFs versus picking individual stocks • Growth stocks versus dividend-paying stocks • Matching portfolio structure to goals, timeline, and risk tolerance • Understanding the risks behind different investments • The long-term impact of fees and advisor costs • Why a complex portfolio is not always a better portfolio • Lessons from high-risk trading and leveraged options • Moving from “making money” to thinking like an investor • Creating a simple, long-term investing process ABOUT KRISTEN WONCH Kristen Wonch is the Founder of Compounding Queens and a wealth coach who teaches women how to understand investing and build diversified, long-term portfolios. With a background in commodities trading and an MBA in finance, she combines financial education with practical portfolio concepts around stocks, bonds, ETFs, risk, fees, and long-term wealth creation. CONNECT WITH KRISTEN WONCH Website: https://kristenwonch.com/ Facebook: https://www.facebook.com/kristenwonch Instagram: https://www.instagram.com/kristenwonch.xox LinkedIn: https://www.linkedin.com/in/kristenwonch Note: This episode is an educational discussion about investing and personal finance. Investment decisions involve risk and depend on individual circumstances, goals, and time horizon. #TheCapitalCEO #Investing #WomenAndWealth #FinancialEducation #WealthBuilding

  8. Oct 1

    EP11 | Build the Business Before the Stage: Visibility, Authority & Paid Speaking | Leslie Jespersen

    What if getting on stage isn’t the hard part, what if the real challenge is becoming the person who can fully own the room once the opportunity arrives? In this episode of THE Capital CEO, Jen Conkey sits down with Leslie Jespersen, speaker trainer, producer, PR strategist, and Founder & CEO of The Leslie Jespersen Experience, to talk about visibility, authority, stage performance, and the business behind becoming known for what you do. Leslie shares how her background in acting, live events, production, and media shaped the way she prepares entrepreneurs and founders for the spotlight. Jen and Leslie discuss why speaker development goes far beyond writing a keynote, including story, embodiment, rehearsal, positioning, confidence, and creating the professional assets that help a speaker get taken seriously. They also explore how speaking can become a revenue channel, why paying for visibility can sometimes function like marketing, what it takes to move from survival-mode entrepreneurship into a scalable business, and how better systems, team support, money management, and authority-building can help a founder grow without doing everything alone. KEY TOPICS • Preparing for the stage beyond simply writing a keynote • Story, embodiment, rehearsal, and performance • Speaker visibility as a business and revenue strategy • Paid visibility and when it can function as marketing • Building your own stage versus speaking on someone else’s • Moving from survival-mode entrepreneurship into intentional growth • Raising prices and letting go of low-value recurring work • Hiring a team and recognizing talent before the job title exists • Creating a culture where clients and team members feel they belong • Money management, automatic allocations, and learning to hold revenue • SOPs, delegation, and shifting from manager to leader • Building authority through PR, media, and a strong digital footprint • Creating a scalable one-to-many offer while preserving community and connection ABOUT LESLIE JESPERSEN Leslie Jespersen is a speaker trainer, producer, and PR strategist who helps entrepreneurs and founders turn their message into a stage-ready, revenue-driving brand experience. Her work combines performance psychology, stage strategy, brand positioning, and talent development to help clients become more visible, credible, and prepared for larger opportunities. She is also the founder of Marsolluna Media and creator of the Everyday Celebrity and Leslie Jespersen Speaker School ecosystems. CONNECT WITH LESLIE JESPERSEN Website: https://www.lesliejespersen.com/ Instagram: https://www.instagram.com/lesliejespersen/ #TheCapitalCEO #PublicSpeaking #PersonalBrand #PRStrategy #BusinessGrowth

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About

Capital CEO features candid conversations with entrepreneurs who have built six-, seven-, and eight-figure businesses by solving real problems and learning how to monetize them. Host Jen Conkey explores the journey behind the growth—what worked, what changed, where profits go, and how successful founders think about capital, opportunity, and what comes next.

Information

  • Creator
    Jen Conkey
  • Years Active
    2026
  • Episodes
    28
  • Rating
    Explicit
  • Copyright
    © Jen Conkey
  • Show Website
    The Capital CEO