The Startup Executive

Hosted by Grayson Faircloth

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May 2024

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Are you a current or future leader at a startup / scale-up company? Tune into The Startup Executive to hear from current executives on what it takes to become an effective startup executive. You'll hear from Founders, C-Suite Executives, and Venture Capitalists on their take on building startups and becoming the next great Startup Executive.

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30 recent

May 1, 20241 hr 13 min

The Vertical SaaS Bug + A Career Switch (w/ Nick Tippmann of TipTop Ventures)

Nick Tippmann's podcast episode delves into his rich entrepreneurial background, influenced by a family legacy of successful business ventures. His early foray into entrepreneurship began with a high school electronics business, which laid the foundation for his commerce skills. At Indiana University, he aimed to learn about starting substantial businesses, a journey that led him to the world of tech startups and venture capital. His pivotal experiences include witnessing family entrepreneurship, discovering tech startups in his senior year, and playing a significant role in the growth of Greenlight Guru in the medical device industry. Nick's educational path took a turn when he chose to drop out of college, opting instead for self-education through influential blogs and books like "Venture Deals" and "The Lean Startup." He actively applied his learning by participating in startup weekends and joining the Brandery Accelerator, which provided valuable networking opportunities. After a period of reflection on his entrepreneurial experiences, Nick decided to join Greenlight Guru, leveraging his expertise in community building and growth marketing to contribute to the company's scaling efforts. Throughout the episode, Nick shares personal preferences such as his love for ketchup over ranch, salsa over guacamole, and being a night owl. He has a penchant for coffee during all-nighters, enjoys concerts more than movies, and favors digital books, particularly audiobooks, over podcasts. Nick's career insights emphasize the synergy of learning with action, the strategic importance of networking, and the necessity of adaptability in the face of market realities. His story is a compelling example of the entrepreneurial spirit, continuous learning, and the importance of adaptability in the dynamic startup landscape. [00:00-06:24] Nick Tippmann: Entrepreneurial Journey and Preferences [08:17-12:08] Defining Moments in a Tech Entrepreneur's Journey [12:38-13:39] Choosing a College Major with an Entrepreneurial Family Background [16:02-17:36] Understanding the Genesis of Large Companies and Tech Startups [17:54-20:41] Reflecting on the Early Realization of Entrepreneurial Ambitions [21:37-25:20] Nick's Pivot from College to Startups and Self-Education [25:51-27:11] Discovering Venture Capital and Self-Education [27:13-28:07] Choosing Self-Education Over Formal Schooling [28:21-31:46] Learning and Action: From Theory to Startup Experience[32:55-34:05] From Startup Weekend to Accelerator: A Founder's Journey [35:33-36:18] Joining Antecs as the Business Lead through the Brandery [36:18-37:54] Reflecting on a Transformative Six-Month Journey [39:32-42:42] Reflecting on Early Entrepreneurial Challenges and Learning Experiences[42:42-44:00] Building a Media Company and Learning from Early Entrepreneurial Experiences [44:00-44:35] Networking and Bootstrapping a Tech Media Startup [50:14-54:09] GreenLight Guru's Vertical SaaS Strategy and Quality Management Software Evolution [01:01:18-01:04:48] Tips for New Angel Investors [01:07:34-01:11:01] Transition from Part-Time to Full-Time Investing [01:12:00-01:12:30] Connecting with Support and Gratitude: A Conversation with Nick Links: Guest: Nick Tippmann: https://www.linkedin.com/in/nicktippmann/ Co-hosts: Grayson Faircloth: https://www.linkedin.com/in/nosyarg/ Crystal Bell: https://www.linkedin.com/in/crystalbell-profile/

April 10, 20241 hr 6 min

Dropout to C-Suite. The Power of Data, Marketing, and HUSTLE. (w/ Shawn Schwegman of CoContent.ai)

Shawn is an entrepreneur with extensive experience in startups and high-growth companies. He has held C-suite roles and has a rich history in sales, marketing, product, technology, strategy, and operations. His success is attributed to unconventional experiences rather than a formal education. Shawn's career began with various jobs, including cooking and sales, before he found his passion in technology. He quickly rose through the ranks at PC Upgrades, leading to significant roles in tech startups. His transition to marketing at Overstock was pivotal, where he grew affiliate marketing revenue significantly and implemented data-driven strategies. Shawn emphasizes understanding customer buying behavior and aligning marketing strategies accordingly. He advocates for rapid testing and learning from failures to refine marketing approaches. At Overstock, he used competitive intelligence and data analysis to drive growth, including using entire product categories as loss leaders to boost overall sales. Over time, Shawn has learned the importance of empathy and celebrating team successes. He acknowledges the need for continuous improvement in his leadership and management skills. Shawn co-founded DemandJump to help marketers make better decisions using data and competitive intelligence. The company initially focused on marketing attribution but pivoted to content optimization using AI, leading to successful outcomes like dominating search rankings for specific topics. Time Stamps: [00:00:09-00:00:51] Introduction of Shawn Schweigman, his background, and what led him to his current success. [00:03:23-00:04:07] Shawn describes himself as a nerd and discusses his strengths in data analysis and technology. [00:04:07-00:04:55] Shawn talks about his current projects, Ulla and co-content.ai, and his passion for AI and marketing. [00:05:05-00:06:21] Shawn reflects on the different eras of his career, starting from his early 20s to his current focus on marketing and technology. [00:07:06-00:09:45] Shawn shares his diverse work experiences before entering the tech industry and the lessons learned from each job. [00:10:01-00:14:04] Shawn recounts his first job in the tech industry at PC Upgrades and his rapid career progression within the company. [00:14:11-00:15:30] Discussion on the importance of learning to sell and Sean's experience with sales in different roles. [00:15:49-00:20:51] Shawn's time at Overstock, his transition from CTO to VP of Marketing, and the strategies that led to significant company growth. [00:21:06-00:22:09] Shawn explains how he grew the affiliate marketing segment at Overstock and the importance of networking and deal-making. [00:23:05-00:25:36] Shawn discusses the use of competitive intelligence data in marketing and how it contributed to Overstock's growth. [00:26:00-00:32:55] Shawn's post-Overstock career, advising companies on growth, and the inception of DemandJump. [00:33:30-00:39:06] Shawn talks about the importance of personalization in marketing and how it varies depending on the context and audience. [00:39:54-00:43:17] Shawn reflects on his leadership style, the importance of celebrating success, and the evolution of his EQ. [00:43:56-00:48:24] The DemandJump era, the initial vision for the company, the challenges with attribution, and the pivot to content marketing with AI.

March 6, 202459 min

How Marketing and Culture Drive Real Enterprise Value (w/ Kyle Lacy of Jellyfish)

In this episode, Kyle Lacy's success in building world-class marketing organizations, authoring books, and transitioning to tech companies showcases his strategic vision and adaptability. His emphasis on leadership, mentorship, and innovative marketing strategies has been instrumental in driving his career forward. Kyle's ability to connect with audiences, foster strong relationships, and take calculated risks has set him apart as a thought leader in the industry. His journey serves as an inspiration for aspiring marketers and executives seeking to achieve success in their careers. Time Stamps: [00:03:12] Rapid Fire Fun Questions [00:07:21] Extracurricular activities and passions. [00:10:56] Ego-driven growth and learning. [00:18:07] Personal branding and content production. [00:20:15] Failing and finding success. [00:25:06-00:25:17] Managing a content marketing team. [00:29:18] Working across different time zones. [00:36:14] Why Lessonly? [00:42:20] Great marketing campaigns. [00:43:02] Taking calculated marketing risks. [00:47:43] Overcoming career failures. [00:54:43] Marketing playbooks and brand voice. [00:57:39] Building a strong professional network.

February 27, 202454 min

Lessons from 400+ Time Entrepreneur (Fred Cary of Idea Pros)

In this episode, Fred shares his journey from building a resume to building a legacy. Having started multiple successful companies and impacted the lives of thousands, Fred's goal is to make a difference in the lives of a billion people. The conversation covers various topics, including Fred's personal brand, his experiences with acquisitions and going public, and his approach to being a well-rounded startup executive. Tune in to learn from Fred's expertise and hear his answers to some pertinent questions. Time Stamps: [00:03:38] Fred’s Rapid Fire Round. [00:07:01] Entrepreneurship and self-discovery. [00:13:15] The reward of entrepreneurship. [00:15:09] Perseverance and Entrepreneurship. [00:19:24] Market analysis importance. [00:23:26] Talking to investors effectively. [00:28:01] Apple's emotional connection with consumers. [00:31:03] Dog walking service growth. [00:37:00] Pro-entrepreneurship and boxing. [00:39:06] Perseverance in business. [00:46:01] Dentistry innovation opportunities. [00:49:51] Advice for young entrepreneurs. [00:52:31] Where to find the book. Links Mentioned: IdeaPros website: IdeaPros.com Fred Carey's Instagram: https://www.instagram.com/officialfredcary/

December 14, 20231 hr 7 min

From Comic Book Dreams to Tech Reality with Mike Reynolds of InnovateMap

Throughout his childhood, Mike Reynolds had always been fascinated by comic books. He was not just an avid reader; he was also a budding artist, drawing superheroes and creating his own comic books. However, as he grew older, Mike realized that his passion for drawing was more a hobby than a career path. His fascination for technology and business steered him towards a different path, leading him to pursue a degree in business and computer science at Purdue University. From there, he began his career in the tech industry during the boom of consulting in the late 90s, working at PriceWaterhouseCoopers and later at Aprimo. In 2014, after nearly 15 years in product management, Mike founded Innovatemap, a company that helps businesses dream, design, and deliver meaningful software products. His journey from a comic book enthusiast to a tech visionary is a testament to his adaptability, passion, and relentless pursuit of knowledge and efficiency. Today, Mike continues to find ways to innovate and drive forward in the ever-evolving landscape of technology. Show Highlights 02:26 Mike reveals his dislike for ketchup and preference for guacamole. 04:04 Mike shares his love for coffee and concerts. 05:12 Mike discusses his reading habits, favoring audiobooks and podcasts for efficiency. 06:22 Mike expresses his preference for podcasts over audiobooks. 07:10 Mike provides a brief background about himself, his family, and his journey into the tech industry. 08:38 The dream of becoming a comic book artist and how it evolved into a tech career. 10:00 Mike’s early career in tech consulting and how he was drawn to software over hardware. 13:52 Mike shares how he knew he wanted to go into tech, attributing it to his interest in business applications and software. 15:47 Grayson discusses how product management became a hot field during COVID. 16:02 Mike’s journey at Aprimo, starting as a software consultant. 17:10 Mike talks about his transition into product management, prompted by his natural instincts and feedback from the Aprimo team. 18:56 Importance of the product’s role in a company. 20:22 Mike discusses the genesis of InnovateMap and the decision to focus on digital products. 22:10 Mike explains the three components of a successful digital product: marketable, valuable, and usable. 24:15 Mike discusses how Innovatemap works with clients to create successful digital products. 26:38 Mike shares how Innovatemap grew organically through the success of the products they helped to create. 28:00 Mike talks about the challenges of managing a growing team and the importance of maintaining the company culture. 32:17 Mike discusses the formation of their early team and the importance of networking in business development. 33:42 Mike talks about the therapeutic and learning benefits he gained from networking. 36:16 Mike emphasizes the value of community and the importance of giving back. 38:36 The approach to balancing work and family life. 43:00 Mike highlights the significance of a founder's passion for the problem they're solving rather than the product itself. 48:26 Mike discusses the challenges faced by technical products in securing funding due to their focus more on the product than the problem it solves. 52:45 The importance of a founder's ability to effectively communicate their vision to their team. 54:16 The significance of having a compelling product narrative that clearly conveys the product's value is discussed. 56:55 Mike highlights the need for a comprehensive understanding of the target market and the problem the product is solving. LINKS MENTIONED Connect with Mike Reynolds on LinkedIn: https://www.linkedin.com/in/mike-reynolds-innovatemap/ https://innovatemap.com/ Connect with Grayson Faircloth on LinkedIn: https://www.linkedin.com/in/nosyarg/ Email: grayson@sonamation.com Connect with Crystal Bell on Linkedin: https://www.linkedin.com/in/crystal-bell-ms-eit/

December 6, 20231 hr 3 min

The Importance of Purpose and Leadership (w/ Lauren James of Mitch Daniels Leadership Foundation)

Lauren James is the executive director of the Mitch Daniels Leadership Foundation (MDLF). She is a Hoosier by birth and choice, hailing from Bluffton, Indiana. Lauren pursued her college education at Ball State University and has had a diverse career, including internships at the Indiana State House, the Lieutenant Governor's Office, and the Indianapolis Colts and a number of roles at ExactTarget and Salesforce before joining MDLF. Lauren is passionate about making a positive impact and is involved in various community organizations, including the United Way of Central Indiana and the Indiana Repertory Theater. She shares insights on relationship management and event marketing, highlighting the importance of building connections and creating memorable experiences. Mentorship has played an important role in her career, so she intentionally dedicates time to mentoring weekly. Ultimately, Lauren believes in the importance of purpose and passion in the professional world and shows up boldly and authentically in her career and in her community. Lauren concludes by discussing her goals for MDLF and the impact she hopes to make in the state of Indiana. Show highlights: 4:43 A background on Lauren’s life 9:23 Don’t be afraid to become a beginner 13:53 Bringing passion into the professional world 22:55 What it’s like to have mentors 25:15 Learnings from the book “Atomic Habits” 27:24 Why it’s never too late to go for “it” 31:35 Doing a little bit of everything 39:39 There is always a platform where you can pour your passion into 48:42 Things that make an event special 51:35 Remembering and connecting with people 1:01:02 Advice to younger self LINKS MENTIONED Connect with Lauren James on LinkedIn: https://www.linkedin.com/in/laurenpetersenjames/ https://www.mdlfindiana.org/ Connect with Grayson Faircloth on LinkedIn: https://www.linkedin.com/in/nosyarg/ Email: grayson@sonamation.com Connect with Crystal Bell on Linkedin: https://www.linkedin.com/in/crystal-bell-ms-eit/ BOOKS MENTIONED: Essentialism: The Disciplined Pursuit of Less - Book by Greg McKeown Atomic Habits - Book by James Clear

November 21, 20231 hr 6 min

How Politics, the Private Sector, and Non-Profit Service Roll-up into a Successful Technology Career with Emily Krueger of 16 Tech

The convergence of public policy, business, and non-profits offers a wealth of opportunities for individuals to make a meaningful impact on their communities. Emily Krueger, CEO of 16 Tech Innovation District, shares her journey from working in the political arena to becoming a startup executive. She discusses the importance of being open to new opportunities and the value of having a broad range of experiences. Emily also highlights the role of government in supporting startups and the challenges and rewards of leading a nonprofit organization. By embracing an entrepreneurial mindset, leveraging government support, and building vibrant startup ecosystems, we can create a future where innovation and community impact go hand in hand. Show Highlights: 01:28 Emily's background and unique perspective as a tech entrepreneur's spouse 03:07 Emily's journey into the political arena 04:18 How Emily ended up working for Senator Lugar 10:04 Why Emily recommends pursuing grad school after professional experience 11:46 The importance of considering function, industry, and geography in career pivots 13:23 Working at Baxter Healthcare and managing Senator Lugar's reelection campaign 16:08 Transferable skills from government sector: adaptability, writing, customer service 18:09 Learning from mentors, observing decision-making, and writing like Senator Lugar 26:53 Why Emily joined LDI 27:48 Variety of experiences for Emily at LDI 30:09 Transition from chief of staff to 16 Tech’s executive role 33:32 Entrepreneurial journey of 16 Tech 38:54 Importance of sustainable business models for non-profits 41:41 Engineering serendipity in the face of COVID 45:58 Government's role in helping startups develop and grow 54:49 Indianapolis' opportunities for young professionals to get involved 55:20 Traits that make an effective board member 57:52 How visibility changes the dynamic of being a startup CEO 58:08 CEO's role as chief storyteller and cheerleader 59:57 How to progress in a career at the intersection of public policy, business, and nonprofits 1:01:40 Importance of seeking roles where you can have the largest impact LINKS MENTIONED Connect with Emily Krueger on LinkedIn: https://www.linkedin.com/in/emilykrueger2010 Check out 16 Tech’s website: https://16tech.com/ Connect with Grayson Faircloth on LinkedIn: https://www.linkedin.com/in/nosyarg/ Email: grayson@sonamation.com Connect with Crystal Bell on Linkedin: https://www.linkedin.com/in/crystal-bell-ms-eit/

October 18, 20231 hr 16 min

Creating and Scaling Successful Learning Programs (w/ Julien Clement of Workato)

Technology and education are now inseparable, and Julien Clement, Director of Certification and Automation at Workato, shares the importance of continuous learning and education for personal and professional growth. He recalls his experience at HubSpot and the challenges of scaling the HubSpot Academy, emphasizing the need to balance quality and quantity in certification programs. Additionally, our guest talks about the effects of artificial intelligence on education, what is required to adjust to the shifting environment, and he offers insightful guidance on how being flexible and having a problem-solving outlook are essential for success in a scale-up business. Show highlights: 1:25 How Julien started on his career 8:25 Seize every opportunity 13:49 Why HubSpot would invest in something that has no ROI 16:46 The people that make up HubSpot 25:02 HubSpot's higher education initiatives 27:24 The push backs that come with partnerships with higher ed 29:17 How to determine what viewers want to see in HubSpot 35:00 How to convince people to dig deep into learning 37:42 Creating a good product with your team 40:19 Challenges that come with scaling user base and goals 50:07 Keeping products up to date 56:44 Transitioning from HubSpot to Workato 1:04:24 Building content strategy in Workato 1:05:24 Big differences of Workato from HubSpot 1:08:40 Will AI replace basic admin works 1:13:50 Advice for people who want to pursue the education space LINKS MENTIONED Connect with Julien Clement on LinkedIn: https://www.linkedin.com/in/julien-pierre-clement/ Connect with Grayson Faircloth on LinkedIn: https://www.linkedin.com/in/nosyarg/ Email: grayson@sonamation.com Connect with Crystal Bell on Linkedin: https://www.linkedin.com/in/crystal-bell-ms-eit/

October 13, 20231 hr 2 min

Growing a B2B Media Startup to $50M+ in Revenue (with Zach Jones of TechnologyAdvice)

In this episode, Zach Jones, the Chief Revenue Officer of TechnologyAdvice, shares his journey from starting as an intern to becoming a C-level executive. He emphasizes the importance of hard work, continuous learning, and outpacing the business. Zach discusses the growth of TechnologyAdvice, the acquisitions they have made, and their focus on owning and building audiences. Our guest also talks about the impact of AI, content, and SEO on their business and the importance of maintaining high-quality, relevant content. With a background in B2B media, Zach has played a key role in TechnologyAdvice's expansion into a worldwide organization. He is passionate about providing better experiences for B2B tech buyers and helping them make informed technology purchasing decisions. Show highlights: 2:07 Zach Jones’ humble beginnings 9:45 Shifting focus to B2B 12:13 Zach’s journey from being an intern to a boss 17:35 The power of reading books and working hard 18:46 Sales is a numbers and effort game 21:04 Be diligent in using your time 23:55 Becoming productive remotely 25:57 Revenue equation explained 30:03 How Technology Advice grew over the past 10 years 37:36 What makes Zach's company unique 40:01 Audience development as the biggest function within the business 41:48 Balancing earning revenue and keeping the audience 45:20 How first-party data plays a direct impact on their business 47:54 Handling time and trust differences between clients 50:43 Bidding for better spots in the newsletter for more traffic engagement 53:27 How to keep subscribers closer 58:18 Venturing into localizing sites to cater to customer requests 59:49 How AI will affect business 1:01:34 Importance of having a growth mindset and say yes to opportunities LINKS MENTIONED Connect with Zach Jones on LinkedIn: https://www.linkedin.com/in/joneszach/ Connect with Grayson Faircloth on LinkedIn: https://www.linkedin.com/in/nosyarg/ Email: grayson@sonamation.com Connect with Crystal Bell on Linkedin: https://www.linkedin.com/in/crystal-bell-ms-eit/

September 27, 20231 hr 5 min

Lessons from a First-Time Founder with Mike Preuss of Visible.vc

Leading a startup company is surely intimidating and comes with tons of ups and downs. But do non’t fear, as it also brings valuable life lessons and satisfying rewards you can use for a lifetime. In this episode, Mike Preuss, CEO and founder of Visible, shares his journey as a first-time founder and the lessons he has learned along the way. He discusses his background in technology and entrepreneurship, his experience in the Orr Fellowship, and how he started Visible to solve the problem of investor-founder communication. Our guest also talks about the importance of trusting your gut as a founder, the value of building relationships with investors, and the key metrics investors care about when evaluating startups. Visible is a platform that helps founders update investors, manage fundraising, and track KPIs in one place. Mike’s background in technology and entrepreneurship and experience as head of business development for Formstack taught him useful skills that he now uses in his own company. He is also passionate about helping founders succeed and has a deep understanding of the investor-founder relationship. Show highlights: 1:33 Mike's humble beginnings 5:34 Orr Fellowship explained 12:30 Hustle and confidence as useful learnings 17:25 The advantages and disadvantages of B2B and B2C 22:57 How Visible grew over the past years 26:45 Advice to first-time time business founders 35:38 Changes in business products 37:30 Raising money as a start-up founder 42:25 Why you need to be educated about financing your company 47:39 Raising funds by frequently updating current investors 52:29 The proper way to communicate with investors 56:04 Early-stage companies are a team more than anything 57:50 Ways to pitch your team as a big strong suit for potential investors 1:03:19 Living with no regrets LINKS MENTIONED Connect with Mike Preuss on LinkedIn: https://www.linkedin.com/in/michaelpreuss/ Email: mike@visible.vc Website: https://visible.vc/ Connect with Grayson Faircloth on LinkedIn: https://www.linkedin.com/in/nosyarg/ Email: grayson@sonamation.com Connect with Crystal Bell on Linkedin: https://www.linkedin.com/in/crystal-bell-ms-eit/