Shows
Bold Moves: How Did You Know?Bold Moves: Momentum-Building Strategies for the Year of the HorseIn this Season 4 finale, I (host Kristen Rocco here!) explore four essential strategies that will help you create momentum for your bold move in 2026—the Year of the Horse.In the Chinese zodiac, the Horse represents unbridled speed and power, making this the perfect year to stop over-calculating and finally accelerate your bold move. However, even a horse at full speed can stumble if it loses its footing; this episode is your guide to surviving the "messy middle" of a bold move where the initial rush fades and the daily work begins.Bringing together the be...
2026-02-1942 min
No Limit Leadership112: The Founder’s Dilemma: Grow or Let Go w/ Mike KrupitMost companies don’t have a culture problem — they have a comfort problem.In this episode, Sean sits down with Mike Krupit — former CTO, COO, and CEO turned leadership advisor and founder of Trajectify — to unpack what really happens when companies scale.They dive into the uncomfortable transitions founders must make, why delegation is emotional (not tactical), how to manage up, and what CEOs should actually spend their time doing. Mike also breaks down why culture must evolve and how high-growth companies avoid stagnation by embracing discomfort.If you’re leading a growing organizati...
2026-02-1639 min
Bold Moves: How Did You Know?He Hid a Secret for 35 Years. How Vulnerability Changed His Life (feat. Mike Krupit, CEO, Trajectify)What if you saw your vulnerability as a superpower rather than a sign of weakness?Mike Krupit spent decades as a Silicon Valley daredevil, launching eight startups and handling millions without flinching, but he admits his most important Bold Move wasn't in business; it was finally taking off the mask he’d worn for 35 years.In this episode, Mike peels back the layers on how he used professional risks to shield himself from personal vulnerability, and why dismantling the "tower" he built around his emotions was the only way to live an...
2026-01-2237 min
Courage to Be CourageousEp. 63 - Mike Krupit comes out as gay late in lifeMike Krupit has a Bachelor's in Computer Science and Applied Mathematics from Queens College in New York graduating in 1985. He started as a software engineer and worked his way up to Chief Technical Officer, and then the Chief Operations Officer and finally CEO of a company called CD Now which sold music on the internet. Mike is now the owner of his own company called Trejectify which is in leadership development, organizational development and business growth coaching. Mike was married for 36 years and has a son who is a teacher in Florida and a daughter that is 29 years old...
2024-07-2343 min
Onwards!InfonautsInfonaut! Ram MohanSeason 1 Episode 6: Ram Mohan. Ram Mohan was hired by two engineering leaders, Mike Krupit and Terry Graber, in 1995. Terry had been working with Ram at a prior company, and he successfully recruited Ram to join Infonautics. Ram confided that he did not interview with the team, it was more of a conversation. They brought Josh Kopelman in for a quick meeting with Ram and they agreed to hire Ram before the end of that day. Ram progressed through the company and wound up in the CTO seat very soon. He was with us in the good times and bad an...
2023-03-1548 min
Onwards!InfonautsInfonaut! Mike KrupitSeason 1 Episode 2: Mike Krupit. Mike was a very early employee at Infonautics, the first outsider after Marvin, Josh and Ron. He was hired in 1994 to be the company's first Director of Software Development. Mike established himself as a very competent leader as the company grew through rapid changes. He has had a great influence on many in the technical world inside and outside of Infonautics. For example he started up the Philadelphia New Tech Meetup. This group has easily impacted over a thousand technology entrepreneurs in the region. Mike also started several other companies, and at one point joined CD...
2023-03-0151 min
Cache FlowE15: House Flipper Turns Tech Founder and Accidentally Builds 300-Person SaaS BusinessJesse Burrell worked in real estate for 5 years before becoming the CEO for BatchService where he helps real estate businesses grow with comprehensive property intelligence and technology. Here are a few of the topics we’ll discuss on this episode of Cache Flow:The important aspects of property flipping.Why people lose money on property investments.Different proactive CSM strategies.The scalability of software companies.What companies need to grow exponentially.The conversion rates for real estate investors.What the process of building a real estate SaaS company looks like.The benefits of bootstrapping a co...
2022-12-281h 04
Cache FlowE12: 8 Lessons from 8 Startups with Trajectify’s Mike KrupitMike Krupit has participated in growing eight companies over 25 years in the Northeast and West Coast.Mike grew from CTO to COO to CEO, while learning a lot about business, leadership, strategy, organization, and operations.Mike’s been involved in extraordinary growth, IPOs, mergers and acquisitions, and even bankruptcies.Today, he is the leader and Founder at Trajectify, providing interim executive and other strategic services to growth-stage companies. Here are a few of the topics we’ll discuss on this episode of Cache Flow:
2022-12-1357 min
Strategic Storytelling072 Entrepreneurs: Get Past Your Comfort Zone With StorytellingYou want to grow a business ... but what happens when you keep telling yourself stories keep you from moving forward? Stories that seem so real and vivid you never think to question them? The truth is, comfort zones are just too ... comfortable. Mike Krupit is an entrepreneur who's consulted with many companies over the years. Mike now supports business owners and entrepreneurs who are serious about developing profitable businesses. Mike talks about how we can get out of our way when we recognize these stories that hold us back. He points out that we...
2022-08-2430 minStrategic Storytelling072 Entrepreneurs: Get Past Your Comfort Zone With StorytellingYou want to grow a business ... but what happens when you keep telling yourself stories keep you from moving forward? Stories that seem so real and vivid you never think to question them? The truth is, comfort zones are just too ... comfortable. Mike Krupit is an entrepreneur who's consulted with many companies over the years. Mike now supports business owners and entrepreneurs who are serious about developing profitable businesses. Mike talks about how we can get out of our way when we recognize these stories that hold us back. He points out that we...
2022-08-2430 min
Level Up PodcastElevating Founders Into CEOs With Mike Krupit, Founder of TrajectifyMike Krupit founded Trajectify, a business and leadership coaching company, in 2013 to help entrepreneurs and small businesses succeed. He has been at the helm of eight diverse startups — including Real Food Works, Novotorium, and CDNOW — and is familiar with the highs and lows of running a business. He began his career as an engineer before discovering his passion for leadership and coaching. During his 30 years of experience, Mike helped a 15-year-old telecommunications company double its revenues to $25 million and spent a decade in Silicon Valley working with two innovative businesses: Verity and KnowledgSet. He moved back to the...
2022-01-2449 min
Money Matters TVMoney Matters TV 22-3 Mike Krupit | TrajecifyMichael Verrill, the Shape Financial Group, and Katie Wenger, CBRE, Inc. speaks with Mike Krupit, Trajecify … Read More!
The post Money Matters TV 22-3 Mike Krupit | Trajecify appeared first on Money Matters TV.
2022-01-1330 min
A Few Things with Jim Barrood#42 Leadership Chat: Mike Krupit + Dom Farnan - A Few Things - 45 MinWe discussed a number of things including: 1. Mike and Dom's entrepreneurial journeys 2. Their outlooks for the regional business/entrepreneurial community 3. What they have learned during the pandemic 4. Advice for entrepreneurs Mike founded Trajectify, a leadership and business growth coaching firm, in 2013 and has worked with dozens of companies, leaders and entrepreneurs. His career was one of growing eight companies, from tech to telecom to food to automotive, both products and services from pre-revenue to $150M+. His passion to partner with and learn from great visionaries helped start and op...
2021-06-1845 min
The Founder's Forge PodcastEpisode 9 - Mike Krupit - People Don't Scale like TechnologyMarcus interviews Mike Krupit, a seasoned veteran of the startup thunderdome who has worn hats from engineer to CEO (and everything in between). Mike is the founder of Trajectify, a business coaching and executive mentoring service helping give startup leaders the momentum needed to overcome the obstacles in front of them. Topics covered include how to validate a service-based business, how to make sure your business isn’t just a lifestyle and a not a business, and an overview of how to break into the coaching space. Marcus and Mike also discuss various company naming strategies, and Marcus inadvertently na...
2020-12-1033 min
Master Your Mindset RadioMYMR 44: Growth Mindset with Entrepreneur Coach Michael KrupitThrough his company Trajectify, Mike Krupit coaches entrepreneurs to grow from early stage to solid success. In this interview he shares his own experience growing his mindset in his career and in his family life. There are so many gems here: how fear is an emotion related to the unknown, recognizing when you need to move on, why listening is so important right now, and how the skills we need to grow as a leader are very much the same skills to grow as a spouse or a parent.
2020-06-2339 min
3 Bald Guys Talk MarketingGuided to Success: Business Coach Mike KrupitIn Episode 14, we speak with business coach Mike Krupit. Attracting clients, and helping his clients attract their own clients, is central to Trajectify.com, Mike's fast-growing business coaching firm. They help business owners successfully navigate steep challenges from marketing and team building to financial operations, while bolstering entrepreneurs' confidence.
This episode was produced with Zoom.
2020-05-1440 min
Learn/Perform Mixtape8.1. Core Coaching CompetenciesWelcome to the CPLP Area of Expertise (AOE) 8: CoachingUsing an interactive process to help individuals develop rapidly and produce results; improving others’ ability to set goals, take action, make better decisions, and make full use of their natural strengths. This section is weighted 8-9% of the exam; 12-14 questions.International Coach Federation (ICF): is a not-for-profit membership organization for professionals worldwide who practice business and personal coachingREAD: What is Coaching? Back to Basics via ATDCoaching: defined by ICF “a professional partnership between a qualified coach and an individual or team that supports the achievement of extraordinary resu...
2019-11-1225 min
Leading Matters with Joel Capperella#40 Mike Krupit Co-Founder CEO IntroNetToday's guest on Leading Matters is Mike Krupit, a veteran of eight diverse startups, both East and West Coast. He is currently the co-founder and CEO of IntroNet, a tech startup with the mission to fill the void of relationship nurturing left by LinkedIn and CRM. , a tech startup with the mission to fill the void of relationship nurturing left by LinkedIn and CRM.
2016-07-1800 min
Internet History Podcast54. CDNow CEO Michael KrupitSummary:Michael Krupit first joined CDNow as the Chief Technology officer. He soon took over COO duties, and eventually rose to become CEO of the entire CDNow operation. Mike gives us the background on the early days of another early ecommerce pioneer, and he gives us some great insights into attempting to dominate a commerce niche as opposed to Amazon’s “everything store” strategy. But just as fascinating is the fact that around the years 2000-2001, Michael was right there in the thick of it when the MP3 and Napster revolutions first rocked the music industry. This is a fasc...
2015-03-021h 02
Internet History Podcast54. CDNow CEO Michael KrupitMichael Krupit first joined CDNow as the Chief Technology officer. He soon took over COO duties, and eventually rose to become CEO of the entire CDNow operation. Mike gives us the background on the early days of another early ecommerce pioneer, and he gives us some great insights into attempting to dominate a commerce niche as opposed to Amazon’s “everything store” strategy. But just as fascinating is the fact that around the years 2000-2001, Michael was right there in the thick of it when the MP3 and Napster revolutions first rocked the music industry. This is a fascinating discussio...
2015-03-021h 02
Internet History Podcast54. CDNow CEO Michael KrupitSummary:Michael Krupit first joined CDNow as the Chief Technology officer. He soon took over COO duties, and eventually rose to become CEO of the entire CDNow operation. Mike gives us the background on the early days of another early ecommerce pioneer, and he gives us some great insights into attempting to dominate a commerce niche as opposed to Amazon’s “everything store” strategy. But just as fascinating is the fact that around the years 2000-2001, Michael was right there in the thick of it when the MP3 and Napster revolutions first rocked the music...
2015-03-0200 min
2015-01-2700 min