Dr. Cindy Gordon, CEO and founder of SalesChoice, joins host Steven Pivnik to discuss her "evolutionary" journey from executive roles at giants like Accenture and Xerox to launching her own tech company. She details how she first joined a venture capital firm to learn corporate finance before co-founding one of the early companies to use AI for predicting sales forecasts.

Cindy provides a refreshingly pragmatic perspective on artificial intelligence, cautioning that not all problems need an AI solution and that true success hinges on a clear use case, good data, and a focus on the "human in the loop". A teacher of AI ethics and law, she also breaks down the critical importance of model transparency, accountability, and navigating the complex global regulatory landscape. For fellow founders, Cindy offers invaluable advice on understanding VC contracts, defining "clawback clauses", and the long-term strategic planning required for a successful exit.

Takeaways:

• Don't use AI just for the hype. Smart investors will (and should) ask if AI is the right technical strategy for your use case. AI is just one technique among many; focus on the best and most appropriate means to build your solution.
• Master the fundamentals for AI success. Whether you're using predictive analytics or generative AI, success always comes down to three things: being crystal clear on the problem you're solving, having high-quality data, and being attentive to the human-in-the-loop adoption process.
• Beware of clawback clauses. In a funding or acquisition deal, a clawback is a contractual hurdle, often tied to revenue, where you can lose equity or cash if you fail to meet an agreed-upon plan. Use good legal counsel to try and remove them, or at a minimum, be extremely confident you can deliver on the proposed targets.
• Plan your exit strategy five years in advance. An exit is a long-term game that requires nurturing relationships. It's a strategy that must be written down, planned, and worked at, much like a comprehensive sales coverage plan.
• Prioritize AI transparency and accountability. You can't sue an algorithm. As a founder, you are accountable and must build transparent, explainable models (not black boxes). This requires strong practices for versioning control, data bias checks, and machine learning ops.
• Build a culture of psychological safety. A great culture is one where people feel safe to be who they are and bring their whole person to work. Cindy's company reinforces this with daily "Hug Huddles", regular feedback, and a focus on authentic, open communication.
• Use strategic alliances to test exit pathways. Forming channel relationships with larger players who have a gap in their portfolio allows you to test synergies and distribution capabilities. This can be a wise strategy, but don't take on too many partners, as they must be actively managed to be effective.

Quote of the Show:

• "Not everything can be solved with AI, so I think I bring a really solid, realistic, pragmatic perspective and just don't get so caught up in the drama."

Links:

• LinkedIn: https://www.linkedin.com/in/drcindygordon/
• Website: https://www.saleschoice.com/ 
• Book Link: https://getbook.at/aidilemma 

David Chase, an avid ultra-marathoner and the President at WorkBoard, joins Steven Pivnik to discuss the powerful intersection between endurance sports and business leadership. David shares how his professional rise to CMO coincided with his running journey, which has included multiple 100+ mile races and even a 200-mile event. He explains that for him, a startup isn't a sprint or a marathon—it's a 200-mile race, with extreme highs and lows that demand resilience and a relentless focus on moving forward. The daily habit of running, he finds, provides essential clarity for processing work challenges and making clearer decisions.
Beyond the mindset, David dives into his work at Workboard, a platform that helps large enterprises align strategy with execution using AI. He details how Workboard's AI agents help managers and teams stay aligned, eliminating the lag and dilution of manual status reporting. He also provides tactical advice for scaling marketing teams, emphasizing the importance of in-person events and treating business goals with the same daily discipline as a marathon training plan. Finally, David shares a practical framework for effective, ongoing sales enablement, including an internal "checkout" process to let reps fail safely before engaging customers

Takeaways:

• Treat Business Goals Like Race Training: Don't just set a quarterly goal and hope to get there. Break it down into specific, daily actions you must take to achieve it, just as you would with a daily training plan for a 5K or marathon.
• Embrace In-Person Connection: In an age of AI and Zoom fatigue, investing in in-person events (like small dinners, meetups, or user conferences) is a powerful differentiator. People crave real experiences and want to connect with real people and customers.
• Use AI to Test and Scale: AI gives marketing leaders the ability to test new channels and initiatives much faster. Use this to run more tests, get data quickly, and then decide whether to scale the initiative or discard it.
• View Sales Enablement as an Ongoing Process: Enablement is not a single meeting or a deck. It requires continuous investment, resources, and the active participation of senior, experienced sellers—not just junior team members.
• Create a "Checkout" Process for Sellers: When launching a new product or pitch, implement an internal certification. Have sales reps pitch to a panel of senior leaders who score them. This provides a safe environment to fail, get feedback, and improve before they are in front of a real customer.
• Reframe Resilience: A startup isn't just a marathon; it's a 200-mile race with much lower lows and higher highs. When things get tough at work, remember that it's rarely as hard as mile 177 of a 200-mile race. The key is to never quit and just keep heading in the right direction.

Quote of the Show:

• "People correlate startups to running a marathon. It's a marathon. It's not a sprint. It's not a marathon, it's a 200-mile race, where the lows are so much lower than a marathon and the highs are so much higher than a marathon."

Links:

• LinkedIn: https://www.linkedin.com/in/davidschase/ 
• Website: https://www.workboard.com/ 

John Ulsh, resilience coach, speaker, and author of "The Upside of Down," discusses the catastrophic car accident that changed his life forever. John shares the harrowing details of the 2007 collision that involved his wife and two young children, leaving him with a less than 3% chance of survival. He takes us through his grueling recovery, which included over 45 surgeries, an 18-day coma, and learning to live with permanent injuries.

Beyond the physical trauma, John delves into the profound mental and emotional journey of rebuilding his life. He discusses how a heartfelt plea from his daughter became the catalyst for him to stop rehab and push his own limits, finding a new purpose in controlled, positive pain through fitness. John explains the key pillars from his book, "The Upside of Down," offering a framework for anyone facing adversity. This is a deeply moving conversation about turning immense struggle into a source of strength, the importance of commitment, and finding profound meaning in the process of recovery rather than just the finish line.

Takeaways:

• Ask "Why" Five Times: When facing a problem, ask yourself "why" five times to drill down to the root cause. This technique helps you move past surface-level issues and identify the core challenge you need to address.
• Focus on Small Wins: In a long and arduous journey, concentrating on the final goal can be overwhelming. Instead, focus on achieving small, daily wins. These incremental victories build momentum and provide the encouragement needed to keep going.
• Embrace the Process, Not Just the Goal: The true growth and learning happen during the training and preparation, not just at the finish line. Learn to love the daily grind and the process of getting better, as that is where the real satisfaction lies.
• Find Pain You Can Control: After experiencing trauma or pain that is out of your control, find a healthy outlet where you can control the discomfort and effort, like exercise. This can shift your relationship with pain from something inflicted upon you to a tool for growth and strength.
• Commitment is the First Step: Before you can tackle any major challenge, you must be fully committed. You have to be in the right headspace and truly ready to take on the journey. Without genuine commitment, even the best plans will falter.
• Don't Be Afraid of Not Finishing: Sometimes, the greatest lessons come from setbacks and failures. Not achieving a goal can provide more profound insights and learning opportunities than success itself.

Quote of the Show:

• "The goal itself was always going to be a letdown. And the beauty, or what I learned, or where the work was done, was in the training."

Links:

• LinkedIn: https://www.linkedin.com/in/john-ulsh-987a6a7/ 
• Website: https://johnulsh-unbreakable.com/ 
• Book Link: https://a.co/d/7A7TS6e 

Dr. Anna Pleet discusses a comprehensive and compassionate approach to tackling obesity and improving overall health. Anna emphasizes that weight loss is far more complex than the simple "calories in, calories out" mantra. She explains her patient-centered method, which begins with listening and understanding an individual's mindset, motivations, and the emotional barriers, like shame, that can prevent progress. She argues that without addressing the underlying mental and emotional components, any dietary changes are unlikely to be sustainable, pointing to the common yo-yo effect seen in many popular weight-loss journeys.

Anna introduces her "Perfect Meal Formula," a sustainable eating strategy inspired by traditional diets like the Mediterranean. The formula focuses on building balanced meals with three key nutrients, protein, fiber, and healthy fats, to optimize metabolism, regulate appetite, and prevent overeating. The conversation also covers practical advice on calculating protein needs based on goal weight rather than current weight and offers compassionate strategies for discussing health concerns with aging family members. Anna leaves listeners with a powerful reminder to proactively commit to physical activities they love, especially as technology makes our lives increasingly sedentary.

Takeaways:

• Adopt the "Perfect Meal Formula": Focus on inclusion rather than restriction. Build every meal and snack around three core components: a source of protein, a source of fiber, and a source of healthy fat to optimize your metabolism and control your appetite naturally.
• Address the "Why" Before the "How": Before starting a health journey, take time for introspection. Lasting change comes from addressing the emotional and mental drivers behind your habits, not just from following a diet plan.
• Calculate Protein Needs for Your Goal Weight: When determining your daily protein intake, base the calculation on your ideal or goal body weight, not your current weight. This provides a more accurate target for fueling your metabolically active tissues. A good starting point for most people is 1 to 1.5 grams of protein per kilogram of their goal body weight.
• Find Your Personal Motivator: Aesthetics are often a short-term driver. Identify a deeper, more meaningful reason to stay healthy, whether it's playing with grandchildren, enjoying a hobby, or reducing medication dependency. Let that be your anchor.
• Reframe Conversations About Health: When approaching a loved one about their weight, focus on what matters most to them. Frame the conversation around their desires and goals—like maintaining independence or participating in family activities—rather than just on the need to lose weight.
• Be Proactive About Movement: As technology encourages a more sedentary lifestyle, it's crucial to intentionally carve out time for physical activities you genuinely enjoy. Don't wait for a health scare; commit now to the activities you want to be doing in your later years.

Quote of the Show:

• "You've gotta take care of your body or it'll break down for you...The adventure is out there, but people need to remember, go seek it."

Links:

• YouTube: https://youtube.com/@annapleetmd 
• Instagram: https://www.instagram.com/annapleetmd
• Perfect Meal Formula Ebook: https://annapleetmd.kit.com/pmf 

Dr. Anna Pleet discusses a comprehensive and compassionate approach to tackling obesity and improving overall health. Anna emphasizes that weight loss is far more complex than the simple "calories in, calories out" mantra. She explains her patient-centered method, which begins with listening and understanding an individual's mindset, motivations, and the emotional barriers, like shame, that can prevent progress. She argues that without addressing the underlying mental and emotional components, any dietary changes are unlikely to be sustainable, pointing to the common yo-yo effect seen in many popular weight-loss journeys.

Anna introduces her "Perfect Meal Formula," a sustainable eating strategy inspired by traditional diets like the Mediterranean. The formula focuses on building balanced meals with three key nutrients, protein, fiber, and healthy fats, to optimize metabolism, regulate appetite, and prevent overeating. The conversation also covers practical advice on calculating protein needs based on goal weight rather than current weight and offers compassionate strategies for discussing health concerns with aging family members. Anna leaves listeners with a powerful reminder to proactively commit to physical activities they love, especially as technology makes our lives increasingly sedentary.

Takeaways:

• Adopt the "Perfect Meal Formula": Focus on inclusion rather than restriction. Build every meal and snack around three core components: a source of protein, a source of fiber, and a source of healthy fat to optimize your metabolism and control your appetite naturally.
• Address the "Why" Before the "How": Before starting a health journey, take time for introspection. Lasting change comes from addressing the emotional and mental drivers behind your habits, not just from following a diet plan.
• Calculate Protein Needs for Your Goal Weight: When determining your daily protein intake, base the calculation on your ideal or goal body weight, not your current weight. This provides a more accurate target for fueling your metabolically active tissues. A good starting point for most people is 1 to 1.5 grams of protein per kilogram of their goal body weight.
• Find Your Personal Motivator: Aesthetics are often a short-term driver. Identify a deeper, more meaningful reason to stay healthy, whether it's playing with grandchildren, enjoying a hobby, or reducing medication dependency. Let that be your anchor.
• Reframe Conversations About Health: When approaching a loved one about their weight, focus on what matters most to them. Frame the conversation around their desires and goals—like maintaining independence or participating in family activities—rather than just on the need to lose weight.
• Be Proactive About Movement: As technology encourages a more sedentary lifestyle, it's crucial to intentionally carve out time for physical activities you genuinely enjoy. Don't wait for a health scare; commit now to the activities you want to be doing in your later years.

Quote of the Show:

• "You've gotta take care of your body or it'll break down for you...The adventure is out there, but people need to remember, go seek it."

Links:

• LinkedIn: https://www.linkedin.com/in/anna-r-pleet/ 
• YouTube: https://youtube.com/@annapleetmd 
• Instagram: https://www.instagram.com/annapleetmd
• Company Website: https://www.ahn.org/ 
• Perfect Meal Formula Ebook: https://annapleetmd.kit.com/pmf 

Hugh Massie, the Founder and Executive Chairman of DNA Behavior, a globally recognized behavioral AI solutions architect, shares his guiding principle for entrepreneurs: "dream big, start small, and finish big." He encourages founders to think beyond financial metrics and focus on the human impact their business can have, even setting goals as audacious as impacting a billion people. He emphasizes the importance of identifying and dominating a niche market channel to become a "category king."

The conversation also delves into the critical, yet often overlooked, topic of wealth management for entrepreneurs, especially pre-exit. Hugh offers practical advice on selecting the right wealth manager, stressing the importance of aligning values and ensuring a personalized approach over chasing the highest returns. He and Steven discuss the common pitfalls entrepreneurs face after a liquidity event, advising a "decision-free zone" for at least six to twelve months to avoid hasty investment mistakes. Finally, Hugh provides a clear framework for founders looking to integrate AI into their current business models, suggesting they focus on both immediate task automation and a complete reimagining of their business for the future.

Takeaways:

• Dream Bigger, Start Smaller: Set audacious, "moonshot" goals for your company's long-term vision, but begin with a focused, manageable starting point. Don't be afraid to aim to impact a billion people, but execute on a small scale first to get the model right.
• Become a "Category King": Instead of competing in a crowded market, design and dominate a new, niche market channel. Identify a sub-market where you can realistically see a path to becoming the undisputed leader.
• Prioritize Human Impact Over Revenue: While revenue is crucial, framing your success by the number of lives you positively impact can lead to greater innovation, a stronger company culture, and a more fulfilling entrepreneurial journey.
• Plan Your Exit Long Before You Sell: Start the process of finding a wealth manager years before you anticipate selling your company. Interview multiple advisors—from small boutiques to large firms—to find one whose values and communication style align with yours.
• Create a Post-Exit "Decision-Free Zone": After selling your business, resist the urge to make any significant investment decisions for at least 6 to 12 months. Give yourself time to adjust to your new financial reality and gain clarity on your purpose before deploying capital.
• Integrate AI in Two Ways: First, look for immediate efficiency gains by automating current tasks within your business (like customer service). Second, empower your innovative team members to reimagine your entire business model and develop new, AI-driven products for the future.
• Don't Sacrifice Your Health or Family: True success is about building a sustainable life, not just a profitable business. Integrate your work with your personal well-being, ensuring you don't lose your health or family in the process of building your company.

Quote of the Show:

• "I go by the motto, dream big, start small, and finish big." 

Links:

• LinkedIn: https://www.linkedin.com/in/hughmassie/ 
• Website: https://dnabehavior.com/ 
• Book Link: https://a.co/d/11Xuut7 

Miles Spencer is no stranger to risk, resilience, and reinvention. A multi-exit entrepreneur, investor, and adventurer, Miles has spent decades building companies in digital media, mentoring founders, and even chasing adrenaline in places like Pamplona and the deserts of the Middle East. Now, he's channeling that same spirit into his most personal venture yet: Reflekta, a platform that allows families to preserve and interact with the voices, likenesses, and stories of loved ones.

In this episode, Miles shares hard-earned wisdom on raising capital, managing leadership transitions, and creating optionality in business deals. He also opens up about the emotional journey of digitally reconnecting with his late father, how storytelling drives meaning, and why entrepreneurship is as much about courage and preparation as it is about innovation.

Takeaways:

• Optionality Creates Leverage: When there's only one buyer, you're stuck. Building multiple options—through cash flow, buyers, or deal structures—gives you leverage to negotiate from strength and avoid desperation.
• Failure Can Be Fuel: A failed venture isn't the end if you preserve relationships. Investors often back founders who learn from setbacks, seeing resilience as proof of future potential.
• Right People for the Right Altitude: Not every teammate is built for the summit. Like mountaineering, startups require different strengths at different stages—and leaders must know when to transition roles.
• Courage Comes from Preparation: Real courage isn't recklessness—it's being ready. Entrepreneurs mitigate risk through training, research, and planning, so they can act decisively when the moment comes.
• Legacy Matters: Success isn't just financial. Miles' work with Reflected AI shows how technology can preserve voices and stories, keeping family connections alive across generations.
• Funding Shapes Values: Who funds you impacts how you operate. Choosing family and friends over institutions can keep your mission aligned with trust, responsibility, and long-term vision.
• Gradual Innovation Prevents Overload: Powerful technology needs to roll out carefully. Step-by-step adoption—text to voice to hologram—helps people adjust, embrace the benefits, and avoid being overwhelmed.

Quote of the Show:

• Entrepreneurship is a bit of a trick, right? You create things that look like daredevil challenges, and everyone says "wow," but then you spend the rest of your time mitigating the risks. It's not that bad—it's not that bad, it's not that bad. With homework, research, training, and so on, the same applies. To a certain extent, entrepreneurship and parenting share a lot of the same dynamics.

Links:

• LinkedIn: https://www.linkedin.com/in/milesspencer/ 
• Website: https://milesspencer.com/ 
• Book Link: https://a.co/d/gO3nHxn 

Adam Vernon, the Founder and Managing Director of Colorado Ski Furniture, shares his incredible story of how he turned a pile of old skis into a thriving and easily recognized business. With nearly two decades of experience, Adam discusses the evolution of his company, from a weekend stress reliever to a full-time venture that exploded during the COVID-19 pandemic. He details his hands-on leadership style and his philosophy of treating employees like family to foster a culture of low turnover and high motivation.

The conversation explores Adam's practical strategies for longevity and growth, including his aggressive approach to product development, where he knows many ideas will fail but the winners will stick. Adam also dives into his marketing tactics, emphasizing the importance of meeting customers on various social media platforms—from Facebook to LinkedIn—and not being afraid to test new channels. He shares how exceptional customer service, especially turning a problem into a positive experience, is key to creating lifelong, loyal customers

Takeaways:

• Embrace Experimentation: Don't be afraid to constantly try new things, even if you anticipate a low success rate. Adam launches new products regularly, knowing that even if only 20% succeed, those "winners" are what drive the business forward.
• Turn Problems into Loyalty: View customer complaints as an opportunity. Adam's philosophy is to do whatever it takes to make a customer happy when something goes wrong. He finds that these customers often become the most loyal and are most likely to return because the company fixed the issue effectively.
• Market Where Your Customers Are, Not Where You Are: As a business owner, you must get out of your own way. Your personal social media preferences are irrelevant; what matters is identifying which platforms your target audience uses and engaging with them there.
• Lead from the Trenches: Foster a strong team culture by being an active, hands-on leader who is willing to do any job, from cleaning the shop to handling difficult customer calls. This "all hands on deck" approach, combined with flexibility and treating staff like family, builds loyalty and reduces turnover.
• Gather Internal Feedback to Streamline Operations: Regularly ask your team which products or processes are the most difficult or time-consuming. This feedback is invaluable for identifying inefficiencies and deciding which products to discontinue, ultimately improving your bottom line and employee satisfaction.
• Listen for the Right Opportunity to Go All-In: A side hustle can be a great way to test a business idea with minimal risk. For Adam, getting laid off from his full-time job was the catalyst he needed to dive in with both feet and commit to making his passion project a success.

Quote of the Show:

• "As an owner, founder, you need to get outta your own way and realize you may not like any of these social platforms... but really, who are your customers and are any of them on there or are all of them on there? If so, that's probably a place you need to be." 

Links:

• LinkedIn: https://www.linkedin.com/in/adamvernoncolorado/ 
• Website: https://coloradoskichairs.com/ 

In this special bonus episode for National Podcast Day episode, our very own, Steven Pivnik, gets interviewed about his experiences so far hosting the Built to Finish podcast. Steven describes his show as informational, motivational, and entertaining, aimed at audacious goal setters, including founders looking to grow, scale, and exit their businesses. He discusses how the podcast extends his brand and allows him to share motivational stories from others. Steven shares that his biggest initial challenge was simply starting, followed by overcoming a "robotic" interview style. He reveals that preparing fewer questions and encouraging a conversational back-and-forth has led to his best episodes. Offering advice to new B2B podcasters, Steven stresses the importance of starting without waiting for perfection and making the listener feel like a "fly on the wall" to a great conversation.

Takeaways:

• Just Start: The most significant challenge is often getting started. Don't wait until you feel 100% prepared or polished; you will improve as you go.
• Aim for Conversation, Not Interrogation: Move away from a rigid, robotic question-and-answer format. Focus on creating a natural conversation to make the episode more engaging for both the guest and the listener.
• Prepare Less to Achieve More: To foster a more natural conversation, try preparing only two or three core questions and allow the discussion to flow organically from the guest's answers. This forces you to practice active listening.
• Empower Your Guests: Encourage your guests to make the interview as conversational as possible, even inviting them to ask you questions in return. Giving them permission to do so can lead to the best episodes.
• Find Your Unique Angle: Identify a gap in your niche. Steven found that while many advisors discuss business exits, the founder's personal perspective was missing, so he positioned his podcast to "speak founder".
• Create a "Fly on the Wall" Experience: Your goal should be to make the listener feel like they are quietly observing a genuine and valuable conversation between you and your guest.
• Don't Fear the Interrupt: If a guest becomes overly scripted or starts rambling, you can use a pattern-interrupt question (e.g., "What is your favorite ice cream?") to break their script and guide them back to a more authentic, conversational state.

Quote of the Show:

• "The hardest part is always to start, you know, people, they wanna have all the answers. They want to be super polished. They need to be a hundred percent prepared. And that's definitely not the case with, it shouldn't be the case with most goals. And definitely for podcasting."

Links:

• LinkedIn: https://www.linkedin.com/in/stevenpivnik/ 
• Personal Website: https://stevenpivnik.com/ 
• Company Website: https://aipadvisory.com/ 
• Podcast: https://podcast.stevenpivnik.com/ 
• Book Link: https://podcast.stevenpivnik.com/ 

Ismael Larrosa, Founder and CEO of the UX-led development company Capicua, joins the show to discuss his entrepreneurial journey, from defying his father's wishes to attend design school to leading one of the fastest-growing companies in the Americas. Ismael shares his philosophy on the significant role luck plays in success, the importance of choosing the harder, more sustainable path, and how founders can manage the emotional highs and lows of the startup world. The conversation also explores practical strategies for stabilizing revenue, the transformative power of generative AI as a tool for both developers and designers, and why the future of the office depends on fostering creativity, not just offering perks.

Takeaways:

• Choose the Harder Path for Long-Term Growth. When faced with two choices, opt for the one that is more difficult but ultimately more sustainable. This approach helps build skills and creates more robust, long-term solutions for clients.
• Stabilize the Emotional Rollercoaster. In the early days of a startup, the highs are very high and the lows are very low. To make the journey less stressful, work on strategies that decrease the frequency and gap between those peaks and valleys for a more manageable ride.
• Escape the "Feast or Famine" Cycle. To create more consistent revenue in a service-based business, you must always be prospecting, selling, and closing. You can further stabilize this by shrinking your scope and focusing on the specific types of clients, problems, and services you are best at.
• Use AI to Enhance, Not Just Accelerate. Treat AI tools like GitHub Copilot as productivity enhancers, not magic wands. The time saved by AI should be reinvested into improving other aspects of the product, such as documentation, quality assurance, and testing, to deliver more value to the customer.
• Make the Office a Hub for Creativity. Forcing employees back to an office only works if you provide value they can't get at home. Instead of focusing on perks like restaurants or gyms, redesign the office experience around collaborative, creative work that solves problems in ways that are not possible in a distributed environment.
• Win on Emotion, Not Just Logic. Competitors can often match logical features, but true differentiation comes from appealing to the user's psychological and emotional needs. As Ismael notes with Apple, a user's feeling about a product is a sign that the company understands them on a deeper level.

Quote of the Show:

• "Design is something that you can't explain logically. You can only explain emotionally." 

Links:

• LinkedIn: https://www.linkedin.com/in/ismael-larrosa-fernandez/ 
• Website: https://www.capicua.com/