The Capital CEO

Jen Conkey

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. 2d ago

    Your Top 5 & Bottom 5: The Leadership Strengths Holding Your Business Back

    What if your biggest leadership strength is actually holding your business back? Most business owners know their strengths. But very few stop to ask whether those strengths are still serving the business they're trying to build. In this episode of The Capital CEO Podcast, Jen Conkey introduces a leadership self-assessment designed specifically for business owners, not employees. Drawing on 22 years in corporate leadership development and her experience building three multimillion-dollar businesses, Jen walks you through 15 essential owner skills and shows you how to identify your Top 5 and Bottom 5 using evidence instead of assumptions. You'll also discover The Strength Dial, a simple way to recognize when the qualities that helped you build your business are now limiting its growth. In this episode, you'll learn: • Why traditional employee assessments don't work for business owners • The 15 essential skills across deciding, selling, leading, building, and lasting • How to score your leadership abilities using proof, not feelings • How to identify the five skills your business needs most right now • Why your greatest strength can become your biggest leadership blind spot • How to uncover your Fit Gaps and recognize when you've turned a strength up too far Your challenge: Identify your Top 5 leadership strengths and share them with someone who has seen you work up close. Ask them which strength you might be overusing, and listen to the answer. This episode brings together three powerful tools from Jen's leadership series: The Fit Gap, The Camera Test, and The Strength Dial. Because building a successful business isn't just about knowing what you're good at. It's about knowing what your business needs from you next. Subscribe to The Capital CEO Podcast for practical insights on leadership, business ownership, and building a business that fits the life you want to lead. #TheCapitalCEO #JenConkey #BusinessLeadership #Entrepreneurship #LeadershipDevelopment

  2. 5d ago

    Stop Overpaying Taxes: Tax Strategy, Grants & Building Wealth | Julio Gonzalez

    What if the biggest tax mistake in your business is not what you pay, but when you start thinking about it? In this episode of THE Capital CEO, Jen Conkey sits down with Julio Gonzalez, Founder and Chairman of Engineered Tax Services, to talk about proactive tax strategy, preserving capital, grants, cost segregation, and the decisions business owners can make before year-end to keep more of what they earn working inside their business and investments. Julio explains why he believes many small business owners approach taxes too reactively. Instead of waiting until tax season to gather documents and file a return, he encourages owners to understand their tax position earlier, while there is still time to evaluate legal strategies, investments, incentives, and planning opportunities. Jen and Julio also discuss cost segregation and other specialty tax strategies, the role of engineers, tax attorneys, and specialized advisors, and why business owners often miss opportunities when they rely only on year-end tax preparation instead of ongoing planning. The conversation expands beyond taxes into grants and government incentives. Julio explains why many small business owners never apply for grants, how AI can help owners identify possible opportunities, and why experienced grant writers and strong relationships can sometimes help businesses move faster. Those experiences shaped his belief in building cash reserves, investing in people, and creating a company strong enough to weather economic cycles. KEY TOPICS • Why tax planning should happen before tax season • The difference between tax preparation and proactive tax strategy • Why year-end timing matters when evaluating tax-saving opportunities • Preserving capital so it can be reinvested into business and assets • How Julio thinks about using tax strategy to support long-term wealth creation • Cost segregation and the role of specialized tax engineering • Why accounting firms may need outside engineers, tax attorneys, and specialty advisors • Tax incentives connected to real estate and other qualifying investments • Using AI to identify potential grants, contracts, incentives, and tax benefits • When working with an experienced grant writer may help • Building cash reserves to survive difficult business cycles • What Julio learned from periods when making payroll was uncertain • Building a culture of care, responsibility, and shared values • Why strategic partnerships can accelerate growth • The role of cost segregation in real estate investing • Turning preserved capital into assets that can compound over time ABOUT JULIO GONZALEZ Julio P. Gonzalez is the Founder and Chairman of Engineered Tax Services (ETS), a specialty tax engineering firm he founded in 2001 to help businesses and accounting firms access advanced tax strategies and incentives. His expertise includes tax engineering, cost segregation, tax incentives, real estate investment, tax reform, business leadership, and wealth preservation. Under Julio's leadership, ETS has grown into a national specialty tax practice serving businesses, accounting firms, and investors across the United States. CONNECT WITH JULIO GONZALEZ Engineered Tax Services: https://engineeredtaxservices.com/ Facebook: https://www.facebook.com/engineeredtax/ LinkedIn: https://www.linkedin.com/in/julio-gonzalez-tax ABOUT THE CAPITAL CEO THE Capital CEO features candid conversations and solo episodes focused on what it takes to build, lead, and grow businesses while making smarter decisions about capital, ownership, and long-term wealth. This episode is for educational and informational purposes only and is not financial, tax, legal, or investment advice. Tax laws and individual circumstances vary, so listeners should consult qualified professionals regarding their specific situation. #TheCapitalCEO #JulioGonzalez #TaxStrategy #BusinessTax #CostSegregation #SmallBusiness #WealthBuilding

  3. Oct 28

    The $1M Video Ad: YouTube Ads, Funnels & Predictable Leads | Aleric Heck

    THE $1M VIDEO AD What if the video you are most afraid to publish is the one that changes your business? In this episode of THE Capital CEO, Jen Conkey sits down with Aleric Heck, Founder and CEO of AdOutreach, to unpack how video, paid traffic, funnels, and data come together to create predictable lead generation. Aleric shares how he started on YouTube at age 12, built AppFind into a channel with hundreds of thousands of subscribers, and eventually discovered YouTube ads while promoting mobile apps. That path led him to launch AdOutreach from college and build a career around helping businesses turn video into qualified leads and clients. One of the most powerful moments in the conversation is also one of the simplest. Years ago, Aleric recorded an ad, watched it back, and almost refused to publish it because he did not like how he looked on camera. He ran it anyway. That ad became the first ad to generate $1 million for his business. From there, Jen and Aleric get tactical. He explains how he uses YouTube and Meta video ads, omnipresent retargeting, URL Affinity Audiences, and value-driven creative to build know, like, and trust while attracting better-fit prospects. Aleric also explains how his team sends qualified-lead data back to the ad platforms to create a feedback loop that improves lead quality over time. Finally, the conversation turns to the numbers CEOs should actually watch. Instead of optimizing around cheap leads or surface-level metrics, Aleric explains why marketing should be measured against the point where it hands the baton to sales: a live, qualified call that actually shows up. KEY TOPICS • How Aleric started on YouTube at age 12 and built AppFind • The $500 YouTube ad test that led to thousands of app downloads • Why Aleric turned down a Silicon Valley opportunity to build his own company • Why video is one of the strongest tools for building trust in an AI-driven market • How to create ads that are useful even if the viewer never buys • URL Affinity Audiences and competitor-based targeting • Why different hooks and educate sections should be tested separately • Why audience sophistication affects funnel design • How to decide whether a booking button should appear immediately or later • Green, yellow, and red lead-routing paths based on prospect fit • Sending qualified-lead data back to ad platforms to improve optimization • Leading metrics versus lagging metrics • How Aleric structures daily, weekly, monthly, and quarterly marketing reviews • Why cheap leads are not the goal • The marketing KPI Aleric prioritizes: live, qualified calls that show up • Why CEOs should benchmark KPIs against their own best performance ABOUT ALERIC HECK Aleric Heck is the Founder and CEO of AdOutreach and a leading authority on YouTube ads and video marketing. He got his start on YouTube at age 12 by building AppFind, which grew to more than 600,000 subscribers. He later launched AdOutreach from his college dorm room and scaled it into an 8-figure company. According to Aleric's official bio, AdOutreach has helped thousands of clients collectively generate more than $300 million in revenue from YouTube ads. The company has appeared on the Inc. 5000 list three years in a row, including a #60 ranking in 2022. Aleric is also the author of Video Authority: The Art & Science of Converting Viewers into Clients. CONNECT WITH ALERIC HECK Website: https://aleric.com/ https://adoutreach.com/ YouTube: https://www.youtube.com/@AlericHeckYT Facebook: https://www.facebook.com/AlericJHeck/ LinkedIn: http://linkedin.com/in/alericheck/ X: https://x.com/AlericHeck Instagram: https://www.instagram.com/alericheck/?hl=en TikTok: https://www.tiktok.com/@alericheck FREE RESOURCE Aleric's Free YouTube Ads Strategy PDF: http://adoutreach.com/gift Video Authority Book: http://videoauthoritybook.com/ #TheCapitalCEO #AlericHeck #YouTubeAds #VideoMarketing #LeadGeneration

  4. Oct 26

    Leadership Style, Behavior & Impact: The Gap You Can't See

    STYLE, BEHAVIOR, IMPACT What if the biggest leadership problem in your business is not what you mean to do, but how people experience what you actually do? In this solo episode of THE Capital CEO, Jen Conkey breaks down the difference between leadership style, leadership behavior, and leadership impact. Most people use those three ideas as if they mean the same thing. They do not. Jen explains that style is how you are wired, behavior is what you actually do and say, and impact is what happens in the other person because of what you did. That impact shapes whether team members speak up, clients come back, buyers say yes, and people take ownership. The challenge is that impact is the one part you cannot see from where you sit. Jen introduces the Camera Test, a simple way to separate intention from observable behavior. Caring about your team is an intention. Asking each person one question about their week is behavior. Through the story of Jay, an agency owner who is fast, capable, and constantly solving problems for his team, Jen shows how a strength can create the opposite result from the one you intended. Jay believes he is helping and saving time. His team experiences constant interruption, stops bringing ideas, and gradually learns to wait for him to make every decision. He did not hire people who lacked ownership. He trained ownership out of them one helpful interruption at a time. Jen also explains why owners often live in a quiet room. Employees may not feel safe telling the truth. Clients may leave without explaining the real reason. Buyers may simply say they need to think about it. No complaints can feel like no problems, even when patterns are forming around you. The goal is not to become a different person. It is to understand where your style works, which behaviors you can change, and whether the impact you think you are having is actually real. KEY TOPICS • The difference between leadership style, behavior, and impact • Why people judge leaders by what they do, not what they meant • How good intentions can still create negative impact • Why the same behavior can land differently with different people • The story of Jay and how helpful interruptions can train ownership out of a team • Why business owners often operate inside a quiet room • Why repeated patterns in other people can point to a behavior in you • How the same leadership style can create opposite results in different business models • The three moves from The Fit Gap: grow, hire, or change • Three specific feedback questions that make it safer for people to tell you the truth • A three-column self-assessment for style, behavior, and impact • How to separate what you know about your impact from what you are only guessing ABOUT JEN CONKEY Jen Conkey is an entrepreneur and investor who has built three multi-million-dollar businesses and replaced herself as CEO in each of them. Before becoming a business owner, she spent 22 years in corporate leadership development. Through THE Capital CEO, she explores business growth, capital, leadership, ownership, and the decisions that shape long-term 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 and solo episodes focused on what it takes to build, lead, and grow businesses while making smarter decisions about capital, ownership, and long-term wealth. This episode is for educational and informational purposes only and is not financial, tax, legal, or investment advice. #TheCapitalCEO #Leadership #FounderLeadership #LeadershipImpact #Entrepreneurship

  5. Oct 23

    Build the Buyer: How Trust & Belief Drive Sales | Eli Wilde

    What if the reason your audience is not buying is not because they do not trust you or your offer, but because they do not yet trust themselves? In this episode of THE Capital CEO, Jen Conkey sits down with Eli Wilde, Founder of Wilde Influence and longtime sales and influence expert, to unpack what actually moves people from listening to deciding. After years as a top salesperson and corporate trainer for Tony Robbins and his companies, Eli has spent decades studying what creates trust, belief, connection, and action in high-stakes conversations. Jen and Eli explore what one-to-many selling really requires. Eli explains why every seminar, webinar, ad, VSL, social post, and stage talk is a presentation, and why the audience is never simply receiving your message. They are filtering it through their own experiences, beliefs, fears, values, and expectations. That means influence is not just about saying the right words. It is about understanding the internal experience your audience is having while you speak. At the center of the conversation is Eli’s Trust Trinity framework. People need to trust the speaker, trust the process or offer, and trust themselves. That third layer is where many presentations fail. Even with a strong offer and an impressive expert, people may still hesitate if they do not believe they can succeed with what is being offered. Eli also breaks down his “Build the Buyer” approach, the role of stories and reframes, the difference between logical and emotional buyers, and why the best presentations are designed around specific beliefs and outcomes rather than a script alone. He shares what he learned from studying Tony Robbins for years, why preparation matters, what should be rehearsed, and why authenticity becomes even more valuable in a world flooded with AI-generated content. KEY TOPICS • Why one-to-many selling is a communication skill, not just a stage skill • Why every webinar, ad, VSL, social post, and live event is a presentation • How audiences filter your message through their own past experiences • The difference between forceful selling and collapsing under pressure • Why connection has to come before conversion • Eli’s Trust Trinity framework: trust the speaker, trust the offer, trust yourself • Why prospects can trust you and still not believe they can get the result • The “Build the Buyer” approach to shaping beliefs before making the offer • How stories, metaphors, reframes, and questions influence decisions • Balancing emotional and logical reasons to buy • Why belief drives thoughts, feelings, decisions, and actions • How to use a presentation to create certainty without sounding manipulative • What Eli learned from decades of studying Tony Robbins’ communication • Why great presenters rehearse key transitions but stay focused on outcomes • Treating a presentation like a valuable business asset • Why authenticity and real trust matter even more during the AI-driven “trust recession” • The role of preparation, repetition, and feedback in becoming a stronger communicator ABOUT ELI WILDE Eli Wilde is the Founder of Wilde Influence, where his work focuses on sales, communication, impact, and influence. He spent years as a top salesperson and top-performing corporate trainer for Tony Robbins and his companies. According to his official site, Eli has coached more than 100,000 people and has been a keynote speaker at more than 3,400 seminars. His teaching centers on authentic influence, trust, storytelling, belief, and communication that helps people make confident decisions. CONNECT WITH ELI WILDE Website: https://wildeinfluence.com/ Facebook: https://www.facebook.com/wildeinfluence/ Instagram: https://www.instagram.com/eliwilde_sales YouTube: https://www.youtube.com/@eliwilde858 LinkedIn: https://www.linkedin.com/in/eli-wilde-459a182 Free Resource, Eli’s Top 4 Influence Frames: https://go.wildeinfluence.com/resource-access #TheCapitalCEO #EliWilde #Sales #Influence #Communication

  6. Oct 19

    The Fit Gap: Why the Right Business Can Still Be Wrong for You

    What if your business is not the problem , but the fit between the business and the person leading it? In this solo episode of THE Capital CEO, Jen Conkey introduces The Fit Gap: the distance between the leader you are today and the leader your business needs. The idea is simple but often overlooked. Every business is a job, and every job has a job description. The work required to run a coaching business is different from the work required to run a product company, service business, consulting firm, or software company. Jen explains why entrepreneurs often choose a business by the prize instead of by the work. They see the income, freedom, lifestyle, or result someone else has created, but rarely stop to ask whether they actually want to do the work that model requires every week. Through examples of coaching, product, and service businesses, Jen shows how a mismatch can look like procrastination, burnout, inconsistency, or even personal failure. She also shares the story of a client who was capable and successful, but struggling in a business model that demanded the wrong kind of work from her. The problem was not her ability. The model and the leader did not match. Instead of automatically blaming the market, the plan, or yourself, Jen offers a fourth place to look: the space between who you are as a leader and what your business needs from its leader. The good news is that a Fit Gap does not automatically mean you need to quit. Once you can see the gap, you have three options: grow into it, hire around it, or change the model. Jen also walks you through a simple five-part self-assessment to identify the kinds of work that feed your energy, the kinds that drain you, and where your business may currently be asking you to operate against your natural strengths. KEY TOPICS • Why every business is really a job with its own job description • Choosing a business by the prize instead of by the work • How coaching, product, and service businesses demand different kinds of leadership • Why a profitable business model can still be the wrong model for you • How a bad fit can feel like procrastination, burnout, or personal failure • The three things owners usually blame: the market, the plan, and themselves • Why avoiding work that consistently drains you can be a signal, not a character flaw • The Fit Gap: the distance between the leader you are today and the leader your business needs • The three moves available when you find a gap: grow, hire, or change • Why you do not have to be everything your business needs • Using complementary strengths when building a leadership team • A five-part self-assessment for identifying where your energy and your business requirements conflict ABOUT JEN CONKEY Jen Conkey is an entrepreneur and investor who has built three multi-million-dollar businesses and replaced herself as CEO in each of them. Before becoming a business owner, she spent 22 years in corporate leadership development. Through THE Capital CEO, she explores business growth, capital, leadership, ownership, and the decisions that shape long-term 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 and solo episodes focused on what it takes to build, lead, and grow businesses while making smarter decisions about capital, ownership, and long-term wealth. This episode is for educational and informational purposes only and is not financial, tax, legal, or investment advice. #TheCapitalCEO #TheFitGap #Leadership #Entrepreneurship #BusinessGrowth

  7. Oct 16

    Build an 8-Figure Movement: Energy, Strategy & Scale | Bridget James Ling

    What if the thing that takes a business from “successful” to truly scalable isn’t more strategy , but learning how to combine vision, energy, data, and disciplined execution? In this episode of THE Capital CEO, Jen Conkey sits down with Bridget James Ling, Founder of Freedom Queen, to talk about building an eight-figure brand, creating a movement people want to belong to, and leading a company without losing the freedom that made you want to become an entrepreneur in the first place. Bridget shares how Freedom Queen grew out of a season of disruption. After leaving New York City during COVID and returning to her childhood bedroom, she began helping women create more freedom in their lives and businesses. What started as coaching around purpose, work, relationships, and personal development evolved into Freedom Queen, an eight-figure company built around the intersection of creativity, leadership, service, and scale. Jen and Bridget unpack Bridget’s “Freedom + Queen” philosophy: freedom as the ability to create, innovate, and move with the market; queen energy as leadership, boundaries, service, team, and responsibility. They also explore why successful companies need both strategy and intuition, how Bridget uses AI and data inside the business, why community and embodiment matter in sales, and how strong brands become movements rather than simply offers. The conversation also gets practical. Bridget breaks down how she maintains high profit margins with a lean team, why she prefers long-term investment strategies, how she thinks about reinvesting capital back into the company, and why bigger is not always better when it comes to events. She shares examples of producing highly profitable events by designing the math around the business instead of copying someone else’s model. KEY TOPICS • Building Freedom Queen from an idea into an eight-figure brand • Why innovation and an “I go first” mentality create authority • The balance between freedom, creativity, leadership, and structure • Using intuition without abandoning strategy and data • Why entrepreneurs have to move with the market instead of clinging to the original plan • How Bridget uses AI and vibe coding to build tools for her community • Turning customer behavior into usable business data • Why simple businesses often outperform overcomplicated ones • Building community, movement, and identity around a brand • Why people buy based on how a leader makes them feel • Becoming the “walking sales page” through embodiment and leadership • Maintaining high profit margins with a lean operation • Reinvesting business cash flow versus investing outside the company • Long-term investing, real estate, and capital allocation • Why bigger events are not automatically better events • Designing events around profit instead of vanity metrics • The importance of negotiation, numbers, and one-to-many selling ABOUT BRIDGET JAMES LING Bridget James Ling is the Founder of Freedom Queen, an eight-figure brand focused on helping women build excellent companies, create influential movements, and expand what they believe is possible in business and life. Her work blends business strategy, leadership, energetics, community, sales, and personal development, with a strong emphasis on building companies that are both profitable and deeply aligned with the founder’s vision. CONNECT WITH BRIDGET JAMES LING Website: https://freedomqueen.com/ Instagram: https://www.instagram.com/bridgetjamesling/ Facebook Community: https://www.facebook.com/groups/freedomqueen LinkedIn: https://www.linkedin.com/in/bridget-james-ling-475684254 Freedom Queen Podcast: https://podcasts.apple.com/us/podcast/freedom-queen-with-bridget-james-ling/id1605847227 #TheCapitalCEO #BridgetJamesLing #FreedomQueen #WomenInBusiness #Entrepreneurship

  8. Oct 12

    The Deals That Lost Money: An $80K Loss and the Deal That Nearly Cost Me Everything

    Everybody talks about the wins. The deal that tripled. The exit. The distribution. In this solo episode of THE Capital CEO, Jen Conkey does the opposite. She breaks down two real estate deals that went wrong, one that cost her $80,000 in a single day, and another that did not lose money but came within days of putting everything she had built at risk. The first loss came from a decision that looked small at the time: Jen skipped an inspection on a property she believed was a “slam dunk.” What followed was an $80,000 loss, the sale of $26,000 in dividend-producing stock to get the property off her books, and five additional flips just to climb back to zero. Her investor did not lose money. Jen absorbed the loss herself. The second deal happened years later, when Jen was experienced, operating at volume, and running ten flips at once. After a market shift created a labor shortage, she made what she believed was the responsible decision to sell one property as-is. Seventeen days after listing it, the lender called the full $170,000 note due in seven days. She ultimately received a 30-day window to close, and finished the deal on day 28, with roughly a $2 million portfolio potentially exposed if the property went into foreclosure. Placed side by side, the two stories reveal the same pattern: hunger, confidence turning into arrogance, and the inability to see risks you have never encountered before. The central lesson is not to avoid making mistakes. It is to start small enough that your education is affordable, because the real risk is making your first serious mistake at a size you cannot survive. KEY TOPICS • Why successful investors rarely talk publicly about the deals that lost money • The skipped inspection that turned into an $80,000 loss • Why the true cost of a bad deal is often more than the amount on paper • Selling $26,000 in dividend-producing stock to get to the closing table • Why Jen made sure her investor did not take the loss • How a labor shortage disrupted a ten-property flipping operation • The lender call that made a $170,000 note due in seven days • Why a foreclosure on one property could have threatened a roughly $2 million portfolio • Hunger, arrogance, and risk blindness as hidden sources of exposure • Why competence can make skipping process feel safe • Why speed is no longer part of Jen’s investment strategy • How liquidity, DSCR requirements, fixed-rate debt, and risk-first underwriting became non-negotiable • Why process matters more than judgment when you cannot see every possible risk 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 #RealEstateInvesting #InvestmentMistakes #RiskManagement #Entrepreneurshipp

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.