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Grayson Faircloth

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The Startup ExecutiveThe Startup ExecutiveThe 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. ...2024-05-011h 13The Startup ExecutiveThe Startup ExecutiveDropout 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.2024-04-101h 06The Startup ExecutiveThe Startup ExecutiveHow 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...2024-03-0659 minThe Startup ExecutiveThe Startup ExecutiveLessons 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....2024-02-2754 minThe Startup ExecutiveThe Startup ExecutiveFrom Comic Book Dreams to Tech Reality with Mike Reynolds of InnovateMapThroughout 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 90...2023-12-141h 07The Startup ExecutiveThe Startup ExecutiveThe 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...2023-12-061h 03The Startup ExecutiveThe Startup ExecutiveHow Politics, the Private Sector, and Non-Profit Service Roll-up into a Successful Technology Career with Emily Krueger of 16 TechThe 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...2023-11-211h 06The Startup ExecutiveThe Startup ExecutiveCreating 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...2023-10-181h 16The Startup ExecutiveThe Startup ExecutiveGrowing 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 k...2023-10-131h 02The Startup ExecutiveThe Startup ExecutiveLessons from a First-Time Founder with Mike Preuss of Visible.vcLeading 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 yo...2023-09-271h 05The Startup ExecutiveThe Startup ExecutiveHow to Run, Scale, and Exit a Professional Services firm with Michael Burton, StitchWhat does it take to become a great CEO? No leader is perfect, but with an exceptional mindset, careful preparation, and the ability to utilize strengths and weaknesses, you can achieve success and inspire others. In this episode, Michael Burton, CEO of Stitch, shares his background in building and scaling professional services businesses. He discusses the importance of being customer-facing and the value of a "Get things done" mentality in project management. Michael also emphasizes the need for a diverse team and the value of finding the right people to complement your weaknesses.  Michael is a...2023-09-221h 10The Startup ExecutiveThe Startup ExecutiveFrom HR to CEO: Dawn Lively-Jenkin's Journey in the Startup IndustryIn this episode, Dawn Lively-Jenkins, chief executive officer and co-founder of Fullstack, walks us through her over 11 years of experience in the human resources industry. She started her career working for a third-party management company that oversaw assisted living and nursing homes in Indiana. She then moved on to work for a professional employer organization (PEO), where she worked her way up to a co-director position. In 2016, Dawn joined Developer Town as their HR lead, and in 2017, she started laying the groundwork for Fullstack PEO. Dawn is passionate about creating a positive and transparent work culture and...2023-09-1357 minThe Startup ExecutiveThe Startup ExecutiveExploring the Intersection of Psychology and Technology with Brian MillisHow is psychology related to business? They both deal with understanding and building relationships with people. In this episode, Brian Millis, a leadership consultant and the vice president of sales and marketing at ADVISA, talks about his education in psychology and liberal arts and how he stumbled into the software startup world. He also shares his experience managing a lab and conducting research on the effects of sleep deprivation on children's behavior and cognitive functioning. Brian reflects on the valuable skills he gained from his first job and why he decided not to pursue a Ph.D.2023-08-291h 14The Startup ExecutiveThe Startup ExecutiveFrom Importing Bikes to Tech Entrepreneurship: A Journey of Success with David KerrIn this episode, David Kerr, managing director at Allos Ventures, a venture capital firm based in the Midwest, shares his entrepreneurial journey, starting from his high school days when he imported bikes from Italy to his experience running various businesses in his twenties. He then transitioned into the tech world and eventually became the CEO of Tinderbox, a software company that was later acquired. David discusses the importance of knowing your risk profile and passion when starting or buying a business. He also emphasizes the value of building relationships and providing support to portfolio companies as a...2023-08-021h 06The Startup ExecutiveThe Startup ExecutiveConnecting the Dots: From Call Center to Sales Assembly with Tanner LaceyHow important is peer learning in sales training and development? It helps you build relationships that are crucial for your overall success. In this episode, Tanner Lacey, head of New Member Sales at Sales Assembly, discusses the significance of establishing relationships and the value of go-to-market strategies. He also provides insights into sales commissions and the common mistakes companies make in their compensation plans. He also emphasizes the need for simplicity and transparency in commission structures. Our guest has a background in early-stage startups and a passion for go-to-market strategies. He is dedicated to helping...2023-07-221h 04The Startup ExecutiveThe Startup ExecutiveHow a College Dropout turned CEO revolutionized the Event Tech Industry (w/ Yarkin S of Socio)Coming up with ideas is great, but executing is better. Yarkin Sakucoglu did both. He found the right people, launched Socio, failed a lot, constantly adapted to the needs of the business, and successfully merged with WebEx Events about 5 years later. In this episode, we are excited to introduce Yarkin Sakucoglu, whose impressive accomplishments have earned him a spot on Forbes' prestigious 30 Under 30 list. Alongside Grayson and Crystal, he shares how he met co-founders, built a company at 19 years old, failed more times than he can remember, and found and gave mentorship along the way. 2023-07-1256 minThe Startup ExecutiveThe Startup ExecutiveBuilding a Scrappy ABM Mindset for yourself and your business (with Mason Cosby of Sales Assembly)What's the benefit of being the least knowledgeable person in a room? It exposes you to the greatest opportunities for learning in your career. In this episode, Mason Cosby discusses the advantages of surrounding yourself with a diverse range of networks, which can eventually lead to finding your tribe. He also recommends intentionally building a network on LinkedIn by sending out connection requests to targeted accounts and writing one's own obituary to live life in a way that aligns with career goals. Mason started as an account executive at a parenting magazine in Mississippi before...2023-06-151h 12The Startup ExecutiveThe Startup ExecutiveThe Startup Executive Welcomes New Podcast Co-host, Crystal Bell!Two minds are greater than one. With another voice and mind, more relevant topics could be explored and discussed, broadening the scope of our knowledge.   In this episode of the Startup Executive Podcast, Grayson Faircloth introduces Crystal Bell as a new co-host, and they discuss their goals for the podcast, which include having conversations with guests about a wide range of topics, learning from their experiences, and helping guests share their stories at scale. They also emphasize the importance of being open to new ideas and perspectives and learning from each other. Crystal and Grayson ha...2023-06-011h 06The Startup ExecutiveThe Startup ExecutiveBuilding World Class Digital Communities and the Importance of Perseverance (with Matthew Volm CEO and Cofounder of Atomic)Have you ever wondered what makes people successful? It's their hard work and perseverance in the face of life's challenges. Rising above failure is the first step towards a new mission and vision for success. In this episode, Matthew Volm, the CEO and co-founder of Atomic, will inspire us to reignite our ambitions and persevere in pursuit of our goals. He will share with us his first and current startups, adding to the collection of stories from his life journey. Matthew shares his insights on how to bounce back from any setback. He'll encourage you t...2023-05-111h 09The Startup ExecutiveThe Startup ExecutiveHow to Activate your Untapped Network in Recruiting (with Scott Sinatra CEO and Co-founder of Bountiful)Are you looking to build an exceptional team? Effective recruitment and referral methods, it is highly possible to attract outstanding candidates. In this episode, Scott Sinatra, CEO and Co-founder of Bountiful, inspires us to elevate our professional and personal capabilities. He shares his success story and how he was inspired to build Bountiful based on his own journey of referrals and recommendations. Scott is optimistic about startups and he shares how he leveraged his own skills and experiences. He also guides us through the process of building a diverse...2023-04-2752 minThe Startup ExecutiveThe Startup ExecutiveFrom Accidental Salesman to Sales Coaching Expert (with Rob Lime from Lushin, Inc)Are you looking to skyrocket your business's sales? Sales are a key indicator of how well a business is performing in the market. Sales coaching can guide us to the next level in the world of business. In today's episode, we are joined by Rob Lime, an integral part of Lushin Inc., who shares with us how to achieve the highest profits through increased sales and improved company performance. He also discusses his personal journey of becoming a sales coach, despite not being a natural salesperson. Rob highlights the importance of sales as a reflection...2023-04-201h 02The Startup ExecutiveThe Startup ExecutiveHow to Maximize Your Professional Development as an Executive (with J. Ryan Williams)Are you interested in learning how to effectively lead your team? Your leadership directly impacts the success of your team. Executive coaching has proven to be a valuable tool for CEOs and executives seeking to improve their leadership skills and guide their companies toward success. In today's episode, we are joined by J. Ryan Williams, CEO of REACH-ABLE, an executive coaching firm focused on revenue leadership teams. Ryan will provide insights on how to effectively handle sales and share his personal story of self-determination that has contributed to his professional success. Ryan's natural curiosity sparked...2023-04-131h 20The Startup ExecutiveThe Startup ExecutiveThe Non-Technical Skills Needed to be an Effective RevOps Leader (with Mallory Lee of Nylas)Marketing is one of the keys to reaching potential customers and boosting sales. That’s why investing in a great marketing strategy designed by experts will help you get ahead of the competition. How can you use marketing to open up more opportunities for your business? In this episode, we have Mallory Lee as our guest. Mallory was a former Marketing Budget and Operations Manager at ExactTarget and the current Operation Vice President of Nylas. With a wealth of experience across both Revenue and Business Operations, she effortlessly juggles leadership duties between the two. Mallory sh...2023-03-1550 minThe Startup ExecutiveThe Startup ExecutiveHelping People and Companies reach their Full Potential (with Joe Jordan of Ship Sigma)Helping People and Companies reach their Full Potential (with Joe Jordan of Ship Sigma) Do you want to set your team up for success? Then surround yourself with amazing people and ask great questions. The opportunity is endless if only you understand the value of connectivity and the power of multiplication. In this episode, we have Joe Jordan, the Chief Revenue Officer at ShipSigma, a supply chain data analytics software that helps shipping companies reduce costs without changing anything operationally in their business. During the conversation, Joe shares his sales leadership journey and...2023-01-1046 minThe Startup ExecutiveThe Startup ExecutiveThe #1 Question That Will Fast Track Your Career Into a Leadership Role (with Sam Estes of Authenticx)Do you want to move quickly from an individual contributor to a leadership role? Then you need to listen to the people around you. Get their ideas and use that information to make decisions and grow. Today, we have Sam Estes, the Senior Vice President of Revenue at Authenticx, a SaaS platform that works with large healthcare providers to help them understand their patients and use it to make informed, proactive decisions. Prior to working with Authenticx, Sam first worked in different sales leadership positions at Aerotek, Paycom, and Bluecrew. He continuously built his career...2022-12-2041 minThe Startup ExecutiveThe Startup ExecutiveWhy Experimentation is More Important than Scale at an Early Stage Startup (with Sara Croft of Innovatemap)What do you think is the best marketing strategy to grow and scale a startup? You probably aren't going to like this, but the hard truth is there is no perfect solution. Everything can change, and to be able to grow, we need to experiment and change for the better. In today's episode, we have Sara Croft of Innovatemap, a digital product agency that helps companies of all sizes dream and delivers valuable digital products and services to the market. Sara was the first marketing hire of the startup and paved her way to becoming...2022-12-121h 09The Startup ExecutiveThe Startup ExecutiveCreating a strong Customer to Product Feedback Loop (with Abby Warner of LaunchCodes)What is the best way to keep customers happy and achieve business success? Connect and communicate with them! Ask for their feedback and use it as a strategy to improve and scale. It gives customers a positive experience and makes your job easier. Today we have Abby Warner, the Co-Founder & COO of LaunchCodes, an e-commerce technology and discovery platform that makes product drops and launches easy, predictable, and secure. Prior to Launch Codes, Abby also worked in different leadership roles in the startup tech space. Her naturally curious and creative problem-solver personality enables her to...2022-12-011h 01The Startup ExecutiveThe Startup ExecutiveHow High Alpha Determines if a startup has Product Market Fit (with Egan Montgomery)Want to grow fast in your career? Then work with the smartest people that you can find. Today, we have Egan Montgomery, the Director of Go-To-Market at High Alpha, a venture studio based in Indianapolis. High Alpha helps B2B SaaS startup founders and companies launch and scale through their unique venture studio model. Egan's passion for helping others and his intentional actions led him to succeed in his career and become a startup leader. In this episode, Egan talks about the role of venture studios in helping startup companies launch and scale...2022-11-2249 minThe Startup ExecutiveThe Startup ExecutiveThe Number 1 Responsibility That Sales Leaders Should Focus On (with Ryan Ketchum of Woven)From student athlete to business owner to sales professional and leader. Different roles with one main goal, to succeed. Ryan Ketchum is the Senior Director of Sales at Woven, a startup tech company designed to help other fast-growing companies seamlessly hire great engineers. Before working at Woven, Ryan began his career as a trainer and successful business owner in the fitness world, building his skills as a great salesperson and leader. Now Ryan utilizes his sales knowledge and leadership experience to lead Woven's sales team. In this episode, Ryan Ketchum...2022-11-161h 04The Startup ExecutiveThe Startup ExecutiveHow Webex Events (Socio) scaled their CX team from 0 to 60 people (with Joe Watkins)A strong customer department is the backbone of a fast growing SaaS business. Joe and the rest of the Customer Team at Socio built a world class customer experience. Listen to learn how!2022-10-1859 min