Leap Academy with Ilana Golan

Chris Savage is a master at pivoting. He co-founded Wistia with his best friend in his living room, originally aiming to create an online filmmaking competition platform. When that didn’t work, they shifted to portfolio tools and later to secure video hosting for businesses, which became Wistia’s core offering. Chris wasn’t afraid to turn down major clients like HBO when their goals didn’t align. Despite running a $300k monthly loss and receiving multiple life-changing acquisition offers, he rejected them and took on $17.3M in debt to continue growing the business. In this episode, Chris opens up to Ilana about the highs and lows of building Wistia, how he made tough decisions, and what it takes to build a lasting business. Chris Savage is the CEO and co-founder of Wistia, a leading video-hosting platform designed to help businesses create, host, and analyze video content in a way that maximizes engagement and drives growth. In this episode, Ilana and Chris will discuss: (00:00) Introduction  (00:19) The Twists and Turns of Launching Wistia (05:02) Pivoting and Finding Success in the Unexpected (08:22) From Zero to Paying Customers (10:14) Rejecting an HBO Deal and Searching for Investors (14:51) How Focus and Authenticity Drive Success (18:02) Building a Serious Business with Fun Marketing (20:33) Learning to Make Tough, Risky Decisions (23:11) Chris’s Secret to Balancing Creativity and Speed (26:34) The Struggle to Close Deals and Break Even (30:31) How He Pushes Through Hard Moments (31:05) Turning Down Life-Changing Offers (35:23) What Chris Learned from Taking Time Off (38:24) The Power of Building a Personal Brand (43:05) Why Wistia is the Top Choice for Video Marketing (46:17) Chris’s Top Business Lessons Chris Savage is the CEO and co-founder of Wistia, a leading video-hosting platform designed to help businesses create, host, and analyze video content in a way that maximizes engagement and drives growth. A strong advocate for the Boston startup ecosystem, Chris is passionate about exploring unconventional paths in tech, entrepreneurship, marketing, video, company-building, and behavioral economics. Before founding Wistia, he contributed to an Emmy Award-winning documentary and, in 2009, earned recognition as a Top Young Entrepreneur by BusinessWeek. Connect with Chris: Chris’s LinkedIn: www.linkedin.com/in/cjsavage Chris’s Twitter: https://x.com/csavage Resources Mentioned: Webinar Wizard: https://wistia.com/webinarwizard  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

At age 12, Russell Brunson was inspired to become an entrepreneur after watching an infomercial about making money. Over the years, he faced massive personal and professional setbacks, from losing 60% of his staff to battling infertility, financial struggles, and nearly going to jail. But instead of giving up, he turned each failure into a lesson, tweaking his approach and ultimately co-founding the multi-billion-dollar company, ClickFunnels. In this episode, Russell shares with Ilana how he transformed his toughest setbacks into the foundation of his thriving business, offering powerful lessons on resilience, success, and the impact of authentic relationships. Russell Brunson is a serial entrepreneur, bestselling author, and digital marketing expert. He is widely recognized as the co-founder of ClickFunnels, a leading marketing software company that helps businesses worldwide boost conversions and drive sales. In this episode, Ilana and Russell will discuss: (00:00) Introduction  (01:54) The Infomercial That Turned Him Into a Young Entrepreneur (05:29) What Wrestling Taught Him About Overcoming Failure in Business (07:55) Launching His First Business, The Potato Gun (09:52) Russell’s Rollercoaster Journey to His First Million (14:25) Key Lessons from His Toughest Year (21:27) The Birth of ClickFunnels (26:61) Finding Fulfillment in Helping Others Succeed (28:58) Leading ClickFunnels Through Its First Major Crisis (34:18) How Serving Tony Robbins Led to Lifelong Mentorship (37:32) Building Lasting Relationships with the Dream 100 Strategy (42:45) The Emotional Story of Russell’s Fertility Journey (44:38) Why Vulnerability in Business Can Lead to Unlikely Success  (46:51) Tips for Building a Winning Team That Drives Your Success (49:58) Turning Your Pain into an Asset Russell Brunson is a serial entrepreneur, bestselling author, and digital marketing expert. He is widely recognized as the co-founder of ClickFunnels, a leading marketing software company that helps businesses worldwide boost conversions and drive sales. Over the past 19 years, he has built a community of over a million entrepreneurs and authored New York Times bestsellers, including DotCom Secrets and Expert Secrets.  Connect with Russell: Russell’s Website: www.russellbrunson.com  Russell’s LinkedIn: https://www.linkedin.com/in/russellbrunson/  Russell’s Instagram: www.instagram.com/russellbrunson  Resources Mentioned: Russell’s YouTube: www.youtube.com/@russellbrunson The 12 month millionaire Droplets: Vincent James's Unmissable Revelations by Vincent James: https://www.amazon.com/month-millionaire-Droplets-Unmissable-Revelations/dp/B0CXJGPXNN  Dig Your Well Before You're Thirsty: The Only Networking Book You'll Ever Need by Harvey Mackay: https://www.amazon.com/Your-Well-Before-Youre-Thirsty/dp/0385485468  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Known for seizing “big, scary opportunities,” Bryan Power has defined his career by embracing risk, adapting to change, and staying focused under pressure. After turning down a promotion at Google for a new challenge at Square, he quickly realized he was in over his head. But it was in facing that discomfort head-on, that he experienced his most significant growth moments. In this episode, Bryan joins Ilana to discuss the importance of tackling challenging opportunities, the practices that lead to career growth, and his unique approach to leadership. Bryan Power is a certified executive coach with over 20 years of experience in human resources management. Having worked with top companies like Google, Yahoo!, Square, and Nextdoor, he specializes in guiding leaders through growth, high-stakes transitions, and fast-paced environments. In this episode, Ilana and Bryan will discuss: (00:00) Introduction  (00:22) His Journey to Silicon Valley  (01:31) Big, Scary Opportunities that Drove His Growth (03:45) Bryan’s Annual Growth Reflection Ritual (05:29) Transitioning from Google to Square (08:40) The Weight of Leadership in Today’s World (10:18) How COVID-19 Impacted the Way We Work (12:37) The Pros and Cons of Remote Work (16:52) Why Adversity Makes the Best Leaders (20:05) How Bryan’s Background Influenced His Success (22:46) Bryan’s Secret to Landing Your Dream Job (25:57) Key Skills Every New Leader Must Master (29:54) Building Trust in Your First 90 Days at a New Job (34:41) Nextdoor’s Success in Digital Community Building (39:37) Career Lessons Bryan Wishes He Had Learned Sooner Bryan Power is a certified executive coach with over 20 years of experience in human resources management. Having worked with top companies like Google, Yahoo!, Square, and Nextdoor, he specializes in guiding leaders through growth, high-stakes transitions, and fast-paced environments. Bryan has a proven track record of building and leading high-performing teams across North and South America, Europe, the Middle East, Australia, and Asia. His expertise extends to board-level work, where he has developed executive compensation strategies, company-wide cash/equity incentives, and benefits programs. Connect with Bryan: Bryan’s LinkedIn: www.linkedin.com/in/bryanpower  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training

Andrew Lacy stumbled into entrepreneurship after failing to land a tech job. His first company did so well that he eventually sold it to Disney. Believing he had business all figured out, he launched another company, only to realize that success wasn’t guaranteed. For his next venture, Prenuvo, Andrew took a more thoughtful approach, but investors repeatedly rejected the idea. Determined to make it work, he bootstrapped and secured loans to launch a clinic in Silicon Valley. Today, Prenuvo is revolutionizing preventive healthcare. In this episode, Andrew shares valuable insights on reinventing yourself, making bold career changes, and pushing through setbacks to bring innovative ideas to life. Andrew Lacy is an Australian serial entrepreneur, angel investor, and the founder/CEO of Prenuvo, a pioneering health tech company using whole-body imaging for early disease detection, including cancer. In this episode, Ilana and Andrew will discuss: (00:00) Introduction  (00:35) From Lawyer to Accidental Tech Entrepreneur (06:44) Lessons from His First Business (13:19) The Pains and Gains of Having a Co-founder (14:59) Starting a Company, Again? (17:24) Cultural Differences in Entrepreneurship (19:57) Tough Truths About Building a Startup (22:44) The Health Scan That Birthed Prenuvo (28:33) Dealing with Investor Rejection (35:11) The Future of Healthcare with Prenuvo (36:35) A Surprising Fact About Andrew (37:56) His Hack for Aspiring Entrepreneurs Andrew Lacy is an Australian serial entrepreneur, angel investor, and founder/CEO of Prenuvo, a pioneering health tech company using whole-body imaging for early disease detection, including cancer. He envisions a future where healthcare is more affordable and accessible, and where people embrace health screenings as tools for long-term wellness. Andrew also co-founded Tapulous, a key player in the early iPhone app ecosystem, later acquired by Disney. He has held leadership roles at McKinsey and Disney. Connect with Andrew: Andrew’s Website: https://andrewlacy.com/ Andrew’s LinkedIn: https://www.linkedin.com/in/andrewllacy/  Leap Academy: Ready to make the LEAP in your career? There is a NEW way for professionals to Advance Their Careers & Make 5-6 figures of EXTRA INCOME in Record Time. Check out our free training today at leapacademy.com/training