
The Thoughtful Entrepreneur
You’re gonna love this DAILY, commercial-free entrepreneur spotlight show. We feature CEOs and founders of 6-9 figure B2B companies. Agencies, coaches, consultants, and other leaders share not only their success stories - but their advice for business leaders focused on business growth.
You’re going to hear real stories from real people all in 15-25 minutes time - perfect for your commute.
On this podcast, your host, Josh Elledge encourages entrepreneurs to share not only their expertise but their stories and their hearts.
We believe that every person has a unique message which can positively impact the world. Even YOU! If you’d like to be featured on The Thoughtful Entrepreneur, apply here: https://UpMyInfluence.com/guest/
Latest episodes

Dec 26, 2023 • 18min
1770 – Custom Advisory with Manny Skevofilax of PORTAL CFO Consulting
In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with the Principal of Portal CFO, Manny Skevofilax.
When asked about the services Manny renders as a fractional CFO, in response, he elucidated that numerous business proprietors initially seek assistance from accountants but often grapple with comprehending profitability and executing data-driven decisions.
Manny underscored the significance of grasping fundamental metrics, such as identifying the most lucrative products or services, to advance towards business objectives.
Manny's professional scope extends across diverse sectors, encompassing service companies, manufacturers, and contractors. He conveyed that a pivotal aspect of his responsibilities involves scrutinizing financial statements.
Each business's financial statement narrates a distinct tale, and the ability to pinpoint areas for enhancement and make informed decisions grounded in financial data is deemed indispensable.
When questioned about his interactions with clients and the concept of engaging a fractional CFO, Manny expounded that he initiates by evaluating the client's existing financial information and their capacity to make informed decisions based on said information.
He stressed the urgency of timely and accurate financial statements, highlighting the significance of promptly addressing adverse trends.
Key Points from the Episode:
Manny Skevofilax's work as a fractional CFO
Importance of analyzing financial statements and making data-driven decisions
Identifying profitable segments in business
Making tough decisions about clients
Overcoming stagnation in business
Manny's experience working with various types of businesses
Importance of basic metrics in understanding profitability
Manny's blog and valuable content on LinkedIn
Manny's approach to providing practical lessons based on his experiences and mentors
About Manny Skevofilax:
Manny Skevofilax, a dynamic consultant and compelling speaker, breathes vitality into businesses, ensuring holistic success through his venture, Portal CFO.
Initially rooted in the restaurant industry, Manny holds a Bachelor of Science in Business and a Master of Science in Finance, leveraging this dual expertise for a seamless transition into the corporate banking realm.
His journey crystallized in consultancy, where his wealth of experience became instrumental. Renowned for translating intricate concepts into actionable strategies, Manny stands as the go-to figure for businesses navigating the ever-evolving commercial landscape.
With a proven track record, he empowers enterprises to survive and thrive, offering indispensable insights for flourishing in today's dynamic business environment.
About Portal CFO:
Portal CFO is a guiding beacon for business owners, dedicated to enhancing financial prosperity. Positioned as a trusted navigator, the mission is clear: facilitate a seamless journey from the current state (Point A) to the business's envisioned future (Point B).
As a financial compass, Portal CFO empowers entrepreneurs to comprehend and bolster their business's economic well-being. The focus is on fostering a more profound understanding, enabling informed decision-making throughout the transformative voyage.
By providing insights into the intricacies of financial health, Portal CFO ensures that business owners not only navigate but thrive, ultimately translating into the ability to make judicious and profitable decisions for sustained success.
Tweetable Moments:
14:32 - "I do everything very, very simple so that the owner can understand, teach it to his or her team, and make it actionable."
Apply to be a Guest on The Thoughtful Entrepreneur:
https://go.upmyinfluence.com/podcast-guest
Links Mentioned in this Episode:
Want to learn more? Check out Portal CFO website at
https://portalcfo.com/
Check out Portal CFO on LinkedIn at
https://www.linkedin.com/company/portal-cfo-consulting/
Check out Portal CFO on Facebook at
https://www.facebook.com/granddynamics/
Check out Manny Skevofilax on LinkedIn at
https://www.linkedin.com/in/timwalther/
More from UpMyInfluence:
We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.
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Dec 25, 2023 • 15min
1769 – The Impact of Team Building Exercises with Tim Walther
In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks to the President of Grand Dynamics International, Tim Walther.
Tim Walther's company is not your typical team-building organization. They specialize in creating outdoor adventure-based retreats and events beyond the usual ropes courses and trust falls.
From multi-day executive retreats to keynote speakers, Grand Dynamics International is all about fostering relationships and enhancing teamwork through unique experiences.
Tim emphasizes the importance of these unique experiences in forging deeper connections among team members. He believes that the familiar can only take you so far, and to truly impact a team, you must introduce novel and creative experiences that generate emotional engagement and connection.
Tim's insight about team building exercises' short- and long-term impact was insightful. He compared motivation to taking a bath, stating that team building experiences must be consistent to have a lasting effect.
The quality of the experience and the engagement of the participants also play a significant role in the impact of these exercises. Well-designed and unique experiences, according to Tim, have a greater impact on team dynamics and relationships.
Key Points from the Episode:
Introduction of Tim Walther, President and Founder of Grand Dynamics International
Grand Dynamics specializes in team-building experiences for corporate teams
Focus on creating unique and creative experiences for deeper connections among team members
Short and long-term impact of team building exercises
Tim's book, "All In Adventure Stories: The Bold Pursuit of Your Potential"
Making adventure more accessible to everyone
Recommendations for event planners and businesses
Information on unique experiences for corporate events
About Tim Walther:
Tim Walther is a seasoned Adventurer, Trainer, Coach, Inspirational Speaker, and Author with over 25 years of experience integrating adventure psychology into business.
Featured in prominent outlets such as The New York Times, Delta Sky Magazine, and Fox Sports News, Tim's training programs have reached 156 countries via The Voice of America.
As the founder of Grand Dynamics International, he employs experiential learning and adventure to enhance leadership and team dynamics.
Tim has authored multiple leadership development and adventure books, contributing articles to various publications.
Renowned for his masterful facilitation, he has conducted leadership programs globally for major companies like Google, Bain Capital, and the Cleveland Clinic.
Based in Jackson Hole, Wyoming, Tim is a dedicated adventure athlete, excelling in Alpine Mountaineering, Endurance Swimming, Free-Diving, and Multi-Sport Adventures.
About Grand Dynamics International:
Grand Dynamics International (GDI) is a pioneering force in experiential training and development, boasting over 21 years of expertise in crafting inspirational corporate events and personalized executive retreats. GDI's Adventure Speakers illuminate meetings, while their experiential events forge indelible memories and team-building programs dismantle barriers, fostering heightened engagement.
GDI excels in customer-centric, cutting-edge experiential training and is dedicated to advancing individual, team, and organizational development.
Their programs, led by a network of professionals ranging from world-class mountaineers to corporate executives, promise unparalleled impact and a direct contribution to improved business outcomes.
GDI's commitment extends to inspiring global action, emphasizing the transformation of potential into tangible results.
Comprising a nationwide and select international network of experts, GDI delivers Team Building Adventures, Leadership Training, Customized Corporate Retreats, action seminars, and Conference Breakout Sessions.
Renowned for dynamic and tailored programs, GDI consistently exceeds client expectations, offering the most impactful team-building events and customised action-oriented seminars to meet specific group needs and business objectives.
Apply to be a Guest on The Thoughtful Entrepreneur:
https://go.upmyinfluence.com/podcast-guest
Links Mentioned in this Episode:
Want to learn more? Check out Grand Dynamics International website at
https://granddynamics.com/
Check out Grand Dynamics International on LinkedIn at
https://www.linkedin.com/company/grand-dynamics-international/
Check out Grand Dynamics International on Facebook at
https://www.facebook.com/granddynamics/
Check out Tim Walther on LinkedIn at
https://www.linkedin.com/in/timwalther/
Check out Tim Walther on Instagram at
https://www.instagram.com/timwaltherallin/
Check out Tim Walther on Twitter at
https://twitter.com/TimWalther
More from UpMyInfluence:
We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.
Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.
What is your #1 Lead Generation BLOCKER? Take my free quiz here.
Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.

Dec 24, 2023 • 16min
1768 – The Most Powerful Sales Techniques with Benjamin Brown
Benjamin Brown, Owner of 360 Sales Consulting, discusses the universal concept of sales and emphasizes the importance of practicing sales skills. He highlights the significance of asking the right questions, understanding clients' needs, and effectively selling your product. With experience in building sales teams, Benjamin shares valuable insights on overcoming resistance and engaging with clients.

Dec 23, 2023 • 21min
1767 – The Importance of Established Leaders with Reggie James
In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with the Founder of Digital Clarity Company, Reggie James.
Digital Clarity, under Reggie's leadership, has been instrumental in helping companies define their value proposition, target the right customers, and create a focused marketing strategy.
Reggie introduced us to the 95/5 rule, which states that 95% of people engaging with a company are not ready to buy and are in the discovery phase.
This rule emphasizes the importance of nurturing potential customers and providing them with the information they need to decide. It's not just about selling but building relationships and trust with your audience.
Reggie also shed light on omnichannel marketing, where companies provide multiple touchpoints for customers to engage with their brand. This approach has become increasingly important in today's digital age, where customers expect seamless experiences across all platforms.
He also highlighted the rise of online communities and buyer committees, where people discuss products and services. These platforms have significantly influenced today's market, shaping consumer decisions and perceptions about brands.
Reggie reflected on his entrepreneurial journey and how it continues to evolve. He mentioned the emergence of new concepts like web3 and NFTs, bringing a new dimension to the business landscape.
Reminiscing about the early days of the dot-com boom and his work at Ziff Davis, a pioneering technology publisher, Reggie emphasized the importance of narrative and depth in marketing.
His experience in the print and advertising industry has shaped his approach to digital marketing, focusing on storytelling and creating meaningful connections with the audience.
Key Points from the Episode:
Digital Clarity's expertise in digital marketing for B2B tech companies
Importance of defining value proposition, targeting the right customers, and creating a focused marketing strategy
The 95/5 rule: 95% of people engaging with a company are not ready to buy
Nurturing potential customers and providing them with information
Omnichannel marketing and multiple touchpoints for customer engagement
Rise of online communities and buyer committees
The value of influence in today's market
Importance of established leaders and track record in the buying decision process
Reggie's commitment to being of service to potential clients
Reflection on the entrepreneurial journey and the evolving business landscape
Mention of web3 and NFTs as new concepts
Importance of narrative and depth in marketing
Digital Clarity's target audience: B2B companies, founders, and CEOs in the tech space
About Reggie James:
Reggie James is a seasoned marketing and digital strategy expert, boasting over three decades of experience in the field. Recognized for his transformative impact on organizations, Reggie has been a critical player in the evolution of digital marketing, actively shaping contemporary business models.
As the founder of Digital Clarity, a leading consultancy, Reggie spearheads innovative approaches incorporating cutting-edge technologies such as AI, analytics, and brand elevation.
Reggie's company is renowned for strategic insights, driving marketing change, and delivering lasting value for clients.
Reggie's unparalleled experience and inventive methods have left an indelible mark on various organizations, leveraging strategic marketing, advertising, and digital solutions.
In an environment where B2B tech companies grapple with delivering results amidst resource constraints, Reggie stands out for providing CEOs and CMOs with invaluable guidance.
His distinctive ability to challenge conventional thinking and deeply understand buyer journeys across diverse industries positions him as a transformative force in marketing and digital strategy.
About Digital Clarity Company:
Digital Clarity is a seasoned player in the dynamic digital marketing landscape, with roots tracing back to the era of iconic devices like the Sony Walkman, PS One consoles, and the Nokia 3310.
With a wealth of experience from collaborations with creative minds in media agencies and digital pioneers, Digital Clarity has continuously evolved its journey.
Today, the company is a valuable guide for businesses of all sizes, navigating the intricacies of the digital economy through well-crafted marketing strategies.
Despite the changing tides of businesses, people, and technologies, Digital Clarity has honed a unique formula for success that has been refined over the years for its diverse range of clients.
With a rich history and a commitment to staying at the forefront of digital marketing, Digital Clarity remains a trusted partner for companies seeking to thrive in the ever-evolving digital landscape.
Apply to be a Guest on The Thoughtful Entrepreneur:
https://go.upmyinfluence.com/podcast-guest
Links Mentioned in this Episode:
Want to learn more? Check out Digital Clarity website at
https://www.digital-clarity.com/
Check out Digital Clarity on LinkedIn at
https://www.linkedin.com/company/mindspansystems/
Check out Digital Clarity on Facebook at
https://www.facebook.com/DigitalClarityLondon/
Check out Digital Clarity on Instagram at
https://www.instagram.com/digitalclarity/
Check out Digital Clarity on Twitter at
https://twitter.com/digitalclarity
Check out Reggie James on LinkedIn at
https://www.linkedin.com/in/reggiejames/
Check out Reggie James on Twitter at
https://twitter.com/ReggieJames99
More from UpMyInfluence:
We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.
Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.
What is your #1 Lead Generation BLOCKER? Take my free quiz here.
Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.

Dec 22, 2023 • 16min
1766 – Embracing AI in Community Banking with Rich Edwards
In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with CEO of Mindspan Systems Inc., Rich Edwards.
Rich Edwards, as the CEO of Mind Span Systems, leads a team that specializes in helping community financial institutions with marketing automation, communication, and personalization using data. They focus on smaller institutions with assets below 10 billion, which may not be technologically advanced but are looking to leverage tools like machine learning and AI to improve their services.
Rich highlighted a phenomenon he called the 'barbell effect' in the banking industry. This effect is characterized by the dominance of large and smaller local banks in the market activity, leaving a gap in the middle. He also discussed the attitudes and trends of banking consumers, emphasizing the fear of another financial collapse and the concentration of activity at both ends of the banking spectrum.
Rich explained that while AI is a powerful productivity tool, it won't immediately replace jobs but rather enhance the capabilities of professionals. He emphasized leveraging AI to focus on tasks that add value and differentiate a business.
Under Rich's leadership, Mind Span Systems helps clients with specific pain points, such as cost savings and support use cases. However, the real value of AI, according to Rich, lies in uncovering new opportunities and tasks that were previously impossible.
Key Points from the Episode:
Introduction of Rich Edwards as CEO of Mind Span Systems
MindSpan's work with community financial institutions
Attitudes and trends of banking consumers
Potential of AI in the banking industry
Barbell effect in the banking industry
AI as a productivity tool that enhances capabilities
Specific pain points and value of AI in uncovering new opportunities
Potential of using interns or assistants to enhance business operations
MindSpan's resources on personalization in the banking industry
About Rich Edwards:
Rich Edwards serves as the CEO of Mindspan Systems, specializing in empowering community financial institutions through data-driven strategies and technologies.
With a profound background in analytics, marketing, artificial intelligence, and machine learning, he guides organizations toward transformative growth.
Throughout his career, Rich has collaborated with global clients in banking, insurance, and financial services, demonstrating his expertise in product strategy related to data center automation and artificial intelligence. Notably, he played a pivotal role in the launch of IBM Watson Developer Cloud.
Rich holds a Bachelor of Science in Engineering from Rensselaer Polytechnic Institute and a Master of Business Administration from the University of North Carolina at Chapel Hill.
Additionally, he served as an engineering officer in the US Army. Currently residing in Raleigh, NC, Rich Edwards and his family contribute to the local community.
About Mindspan Systems Inc.:
Mindspan Systems assists mid-market insurance, banking, and financial institutions with data-related challenges.
Recognizing the frustration stemming from limited insights, the company facilitates the execution of data-driven strategies, fostering transformative changes and securing a sustainable competitive advantage.
Mindspan Systems offers various services, including data science and data-driven technology solutions.
These empower organizations to construct personalized experiences tailored for each customer, utilizing laser-focused, trackable, and testable messaging to optimize marketing budgets for customer acquisition and increased wallet share.
The company prides itself on providing expertise and flexible, scalable solutions to meet specific requirements. Mindspan Systems stands ready to contribute its technical prowess and ensure the success of your organizational strategy.
Apply to be a Guest on The Thoughtful Entrepreneur:
https://go.upmyinfluence.com/podcast-guest
Links Mentioned in this Episode:
Want to learn more? Check out Mindspan Systems Inc. website at
https://mindspaninc.com/
Check out Mindspan Systems Inc. on LinkedIn at
https://www.linkedin.com/company/mindspansystems/
Check out Mindspan Systems Inc. on Facebook at
https://www.facebook.com/mindspansystems
Check out Rich Edwards on LinkedIn at
https://www.linkedin.com/in/richedwards/
Check out Rich Edwards on Twitter at
https://twitter.com/richedwards
Check out Rich Edwards on Instagram at
https://www.instagram.com/mindspan_systems
More from UpMyInfluence:
We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.
Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.
What is your #1 Lead Generation BLOCKER? Take my free quiz here.
Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.

Dec 21, 2023 • 17min
1765 – The Power of Authenticity and Quick Action with Whitney Alexandra
In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with Performance Coach, Whitney Alexandra.
Whitney's clientele consists of successful women who have already achieved a multi-six figure level in their businesses. However, they often find themselves at a plateau, whether a sales or revenue plateau or a passion plateau, where they feel disconnected from their business. This is where Whitney steps in, helping them get clear on their next success level and find the easiest path to achieve it.
Whitney suggests an exercise to help listeners get started on the path to clarity. She advises thinking about their considerable revenue or business goal and multiplying it by ten. This brainstorming activity opens up creative options and can be a game-changer.
Whitney emphasizes that her approach is not about working harder but about doing less more smartly. She helps her clients delegate and streamline their operations for maximum efficiency.
Whitney Alexandra is no stranger to recognition. She has received accolades from a consulting firm for her exceptional sales performance. However, she acknowledges that, like everyone else, she is not immune to making mistakes and getting in her own way.
In the age of social media, she discusses the concept of authenticity and how she is working on creating more candid content to share important stories and insights.
Whitney emphasizes the need to take action quickly and not wait for the perfect moment or appearance. She encourages her clients to remove the pressure of perfection and focus on what is fast and easy.
She shares a success story of a client who had been delaying sending an email to their list but ended up making $100,000 in sales that week after embracing the idea of speed and imperfection.
Key Points from the Episode:
Whitney Alexandra's work as a performance coach for women leaders and entrepreneurs
Helping clients scale their businesses in alignment with their desires and fulfillment
Assisting clients in overcoming plateaus in their business and finding clarity in their goals
Encouraging clients to think bigger and ask new questions to break out of their comfort zones
Suggesting an exercise of multiplying big revenue or business goals by ten for creative options
Emphasizing the importance of working smarter, not harder, and delegating tasks
Reflecting on personal experiences and mistakes and the concept of authenticity in social media
Encouraging taking quick action and embracing imperfection for faster results
Discussing the humanizing aspect of vulnerability and connecting with others facing similar challenges
About Whitney Alexandra:
Whitney Alexandra is a renowned Performance Coach who empowers top women entrepreneurs to achieve unprecedented success and lead extraordinary lives. With over two decades of experience, Whitney has become a trusted guide for influential business owners seeking to unlock their full potential.
Employing evidence-based performance coaching strategies, Whitney facilitates rapid and transformative shifts for her clients, often elevating every aspect of their personal and professional lives within a few short months.
In recognition of her expertise, Whitney was honored as a prestigious Forbes Business Council member in 2023. She is a thought leader and contributor on this global platform, actively engaging in higher-level conversations and fostering connections for women entrepreneurs worldwide.
Whitney's coaching philosophy centers around rewiring mindsets for limitless success. Her 20-year journey includes assisting some of the world's most reputable brands and leaders in their transformative endeavors.
Through a unique blend of performance coaching, mindset tools, and tailored strategies, Whitney focuses on clearing subconscious, energetic, and emotional blocks to enable her clients to embrace the incredible lives they deserve.
As a beacon of empowerment, she guides individuals to unleash their inner potential and emerge ready to receive the success they desire.
Tweetable Moments:
11:40 - "In this world of being real on social media, there's something really nice about showing up and not having to look 100% or being in a you know going live and talking about your business or your offers."
Apply to be a Guest on The Thoughtful Entrepreneur:
https://go.upmyinfluence.com/podcast-guest
Links Mentioned in this Episode:
Want to learn more? Check out Whitney Alexandra’s website at
https://whitneyalexandra.co/
Check out Whitney Alexandra’s company on LinkedIn at
https://www.linkedin.com/company/whitneyinc/
Check out Whitney Alexandra on LinkedIn at
https://www.linkedin.com/in/whitneyalexandra/
Check out Whitney Alexandra on Facebook at
https://www.facebook.com/WhitneyInc
Check out Whitney Alexandra on Instagram at
https://www.instagram.com/whitney.alexandra/
More from UpMyInfluence:
We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.
Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.
What is your #1 Lead Generation BLOCKER? Take my free quiz here.
Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.

Dec 20, 2023 • 19min
1764 – The Future of AI-Powered Feedback with Ryan Glasgow
In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with the Founder & CEO of Sprig, Ryan Glasgow.
Sprig is a platform that helps businesses gather user feedback through in-product surveys, session replays, and data analysis with artificial intelligence. They've worked with big names like Netflix, Dropbox, Robinhood, Coinbase, and Peloton, ensuring these companies get a representative sample of user experiences.
Ryan shared that Sprig has an impressive response rate of 33% for their surveys. He compared this to platforms like Yelp, where only a small percentage of users leave reviews, but those reviews are generally accurate representations of the overall experience.
Ryan emphasized the importance of understanding user experience. He cited companies that have faced backlash and struggled due to a lack of customer perception.
In his view, companies that don't prioritize understanding their customers may lack empathy and risk falling behind in a competitive and challenging economic environment.
One of the most exciting aspects of Sprig is its implementation of AI for data analysis. Ryan explained that they use advanced AI models to summarize and analyze large amounts of survey data.
This provides meaningful insights and even suggestions for improving the product experience. The potential for conversations with AI entities that understand the data and can help make decisions based on customer feedback is groundbreaking.
Key Points from the Episode:
Introduction of Ryan Glasgow, founder and CEO of Sprig
Sprig's services in gathering user feedback for companies like Netflix, Dropbox, Robinhood, Coinbase, and Peloton
Comparison of Sprig's high response rate for surveys to platforms like Yelp
Importance of understanding user experience and its impact on companies
Implementation of AI for data analysis and providing insights and suggestions for product improvement
Potential applications of Sprig for large enterprise-level companies and early-stage startups
Vision for the future of Sprig and advancements in AI
Importance of valuing customer feedback and increasing customer loyalty
Future of delivering exceptional experiences through targeted surveys
About Ryan Glasgow:
Ryan Glasgow, Founder and CEO of Sprig (formerly UserLeap), is a seasoned figure in the tech industry. His brainchild, Sprig, is a research platform specializing in advanced usability testing and in-product survey capabilities, catering to renowned companies like Dropbox, Loom, and Shift.
An accomplished author, Glasgow penned "The Customer-Obsessed Product Manager's Playbook" and currently hosts the People Driven Products Podcast.
He has a robust product management background and previously held key roles such as group product manager at Weebly, product manager at Vurb, and product designer at Extrabux.
Ryan's contributions to the industry underscore his expertise in enhancing user experience and driving product innovation.
Sprig:
Sprig is a dynamic product insights platform that empowers teams to enhance their products through swift user insights. Its capabilities span from testing new designs and prototypes to optimizing core user flows.
Trusted by prominent companies, including Dropbox, Square, Notion, and Loom, Sprig is pivotal in enabling these teams to construct superior product experiences on a large scale.
Sprig contributes to the evolution of user-centric designs and refining essential user interactions by facilitating rapid and informed decision-making.
Its impact is evident in the tech landscape, where it serves as a valuable resource for organizations committed to staying at the forefront of product innovation and ensuring optimal user satisfaction.
Apply to be a Guest on The Thoughtful Entrepreneur:
https://go.upmyinfluence.com/podcast-guest
Links Mentioned in this Episode:
Want to learn more? Check out Sprig website at
https://sprig.com/
Check out Sprig on LinkedIn at
https://www.linkedin.com/company/sprig-official
Check out Sprig on Twitter at
https://twitter.com/Sprig
Check out Ryan Glasgow on LinkedIn at
https://www.linkedin.com/in/ryanglasgow/
Check out Ryan Glasgow on Twitter at
https://twitter.com/ryanglasgow
More from UpMyInfluence:
We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.
Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.
What is your #1 Lead Generation BLOCKER? Take my free quiz here.
Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.

Dec 19, 2023 • 16min
1763 – The Importance of Effective Data Utilization with Eric Dodds
In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks to the Head of Product Marketing of RudderStack, Eric Dodds.
RudderStack is a customer data platform designed to help businesses collect, integrate, and utilize customer data. It's a tool that breaks down data silos, providing a comprehensive view of the customer journey.
This platform offers tools to analyze and utilize data effectively, such as identifying potential churn customers and prioritizing leads for the sales team.
Eric highlighted the consequences of not working with data effectively. These include difficulty in making decisions and challenges in team collaboration. Understanding past performance and making informed decisions becomes a daunting task without proper data analysis.
Conflicting data across different teams can also hinder collaboration and alignment. Rudder Stack aims to solve these challenges by providing a data infrastructure that enables businesses to leverage their data for growth.
Eric explained that RudderStack's pricing model is based on a volume basis. Customers are charged based on the amount of data they send through the system. The simplicity of their pricing structure is a testament to their belief in keeping things simple for their customers.
Eric also shared some background information about RudderStack. The core of their product is open source, providing high transparency for customers. This transparency is a key part of RudderStack's commitment to helping businesses of all sizes, from startups to enterprise-level organizations, effectively utilize their data.
Key Points from the Episode:
Introduction of Eric Dodds, Head of Product Marketing at RudderStack
Discussion on RudderStack, a customer data platform
Features and benefits of RudderStack
Target audience of Rudder Stack (data leaders in companies of all sizes)
Data privacy and security
Consequences of not working with data effectively
RudderStack's mission to provide a data infrastructure for growth
Pricing model of Rudder Stack (volume-based)
Best practices for early-stage companies using Rudder Stack
About Eric Dodds:
Eric Dodds, a resident of South Carolina, is a multifaceted individual with a passion for technology, mountain activities, and, notably, strong coffee. His commitment to faith and role as a loving husband are central aspects of his life.
As the founder of Yield Group, a marketing technology company, Eric leads efforts to empower businesses by facilitating the collection, processing, analysis, and actionable use of essential data for growth.
Eric boasts a rich professional history, having co-founded and overseen marketing at The Iron Yard, which evolved into the world's largest in-person code school.
His extensive marketing experience spans agency and client roles, contributing to renowned brands such as Best Buy, Double Day, and Colonial Williamsburg.
Beyond the professional realm, Eric dedicates time to family, enjoying activities like reading, mountain biking, and crafting in his workshop.
About RudderStack:
RudderStack is the foremost warehouse Customer Data Platform, uniquely tailored for data teams. Distinguished by its integration with existing warehouses or data lakes, RudderStack operates without storing data internally, addressing security apprehensions, cutting costs, and optimizing the potential of warehouse investments.
Trusted by prominent companies such as Stripe, Crate and Barrel, Priceline, and Footlocker, RudderStack is the conduit for these enterprises to efficiently collect and transmit their invaluable data to the requisite tools and teams.
With a commitment to innovation and reliability, RudderStack emerges as a pivotal solution, facilitating seamless data management and utilization for diverse businesses.
Apply to be a Guest on The Thoughtful Entrepreneur:
https://go.upmyinfluence.com/podcast-guest
Links Mentioned in this Episode:
Want to learn more? Check out RudderStack website at
https://www.rudderstack.com/
Check out RudderStack on LinkedIn at
https://www.linkedin.com/company/rudderstack
Check out RudderStack on Twitter at
https://twitter.com/RudderStack
Check out Eric Dodds on LinkedIn at
https://www.linkedin.com/in/ericdodds/
Check out Eric Dodds on Instagram at
https://twitter.com/ericdodds
More from UpMyInfluence:
We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.
Are you a 6-figure consultant? I’ve got high-level intros for you. Learn more here.
What is your #1 Lead Generation BLOCKER? Take my free quiz here.
Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.

Dec 18, 2023 • 16min
1762 – Law Firm Strategy with Demetrio Rico & Raquel Gomes of Stafi
In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with the Chief of Operations & Founder of Stafi, Demetrio Rico & Raquel Gomes.
Demetrio explained that Stafi's vetting and screening process is incredibly rigorous, with only 1% of applicants cutting. This ensures that only the best and most qualified individuals are hired.
Stafi takes pride in training its staff in-house and providing ongoing support to ensure they add value to the law firms they are paired with.
They don't just provide staff; they act as an extension of the law firms, handling onboarding, continuous education, and training for the virtual team. They even have a full-time psychologist dedicated to supporting the staff, which is a testament to their commitment to their employees' well-being.
Raquel added that Stafi offers different types of coaches to support the virtual staff representatives. Their client success team is in constant touch with the law firm owners, acting as their business partners.
Demetrio and Raquel emphasized helping law firms and lawyers with business development and sales strategies. They pointed out that many law firms mistakenly believe they need to hire more paralegals when what they need is to free up their time and focus on growing their business.
Stafi aims to help them find someone who can handle certain aspects of their business just as well, if not better, than they can, allowing them to scale their business to the next level.
Key Points from the Episode:
Introduction of Demetrio Rico and Raquel Gomez, co-founders of Stafi
Overview of Stafi's services for law firms specializing in virtual staffing
Strict vetting and screening process for hiring virtual staff
In-house training and ongoing support for virtual staff
Different types of coaches and client success teams for support and engagement
Advantages of partnering with Stafi instead of recruiting locally
Importance of helping law firms with business development and sales strategies
Empathy and sales skills in a receptionist or intake person role
Negative impact of interruptions on efficiency
About Raquel Gomes:
Raquel Gomes, a passionate entrepreneur and advocate for women in business, hails from the south of Brazil. Armed with a unique blend of expertise as a licensed psychologist with an MBA in International Business, Raquel is the founder of Stafi.
Her company specializes in sourcing highly qualified offshore staff, enabling business owners, particularly women entrepreneurs, to focus on core tasks that drive client satisfaction and business growth.
Having excelled as a sales Rockstar and a leader of Rockstar Sales Teams, Raquel emphasizes the importance of balancing professional success with cherished moments with loved ones and self-love. Despite her success in business, family and friends hold paramount importance in her life.
A fascinating aspect of Raquel's journey is her upbringing without television until age 16, instilling in her a unique perspective on screen time and fostering a creative mindset, a principle she now applies in raising her daughter.
About Demetrio Rico:
Demetrio Rico, a seasoned professional with over two decades of experience, has significantly impacted the global telecommunications sector through his leadership in successful sales teams.
Demetrio recently served as the Global Vice President of Sales for 2600Hz, contributing to the company's rapid growth. Before this role, Demetrio held key positions, including Global Director of Service Provider Development for Five9, where he played a pivotal role in launching cloud contact centers for service providers.
His extensive journey includes serving as Director of Customer Experience for Cisco and as Global Vice President of Professional Services for Broadsoft, leading a substantial team with an impressive annual revenue of over 16 million dollars.
Demetrio's wealth of team management experience and business skills led him to his current role as Stafi's Chief Operating Officer, marking a new chapter in his impactful career.
About Stafi:
Stafi is a dynamic company that boasts a skilled team comprising executive and personal assistants alongside customer service specialists. With a commitment to providing scalable and flexible staffing solutions, Stafi caters to the needs of global legal firms and tech companies.
Their services encompass diverse professional roles and promise cost-effective and low-risk staffing solutions.
By offering a mix of executive and personal assistants, Stafi addresses the multifaceted demands of businesses, allowing them to optimize their workforce efficiently.
The company's emphasis on scalability and flexibility ensures that clients can adapt their staffing needs according to the evolving requirements of their projects or operations.
Stafi's innovative approach aims to enhance efficiency and reduce costs, making it a valuable partner for legal and tech entities seeking reliable and adaptive staffing solutions.
Apply to be a Guest on The Thoughtful Entrepreneur:
https://go.upmyinfluence.com/podcast-guest
Links Mentioned in this Episode:
Want to learn more? Check out Stafi website at
https://getstafi.com/
Check out Stafi on LinkedIn at
https://www.linkedin.com/company/getstafi/
Check out Stafi on Facebook at
https://www.facebook.com/Get-Stafi-104530455195319
Check out Stafi on Instagram at
https://www.instagram.com/getstafi/
Check out Raquel Gomes on LinkedIn at
https://www.linkedin.com/in/raquel-gomesstafi/
Check out Raquel Gomes on Instagram at
https://www.instagram.com/getstafi/
Check out Demetrio Rico on LinkedIn at
https://www.linkedin.com/in/demetriorico/
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Dec 17, 2023 • 17min
1761 – Go-To-Market Strategies with Whitney Stowell of Cribworks LLC
In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks to the CEO & Founder of Cribworks, Whitney Stowell.
Whitney's expertise lies in helping companies build their sales pipelines and account management plans to position themselves for success. In our conversation, she shared invaluable insights every business owner should know.
Whitney's work involves identifying leaks in the sales pipeline and addressing why leads may not convert into demo meetings or potential proposals.
She emphasizes the importance of vetting opportunities and understanding the customer's needs and preferences, especially in larger enterprise-level deals.
Whitney also mentioned the importance of professional associations as a valuable source of warm leads and partnership opportunities. These associations provide a platform for networking and building relationships that can lead to potential business opportunities.
In terms of sales cadences, Whitney suggests considering whether there is a compelling event or reason for the customer to move forward with the opportunity. She emphasizes the importance of understanding the customer's motivations and needs to avoid spinning wheels on unproductive engagements.
Whitney advises against being pushy or solely focused on selling. Instead, she suggests leaning into the role of a trusted advisor and treating customers like friends. By genuinely advocating for their best interests, you can create the best possible outcomes for them.
Key Points from the Episode:
Introduction of Whitney Stoll, CEO and Founder of Carriageworks
Focus on building sales pipelines and account management plans
Identifying leaks in the sales pipeline and addressing conversion issues
Importance of vetting opportunities and understanding customer needs
Role of emotions and relationships in sales, particularly in government contracting
Importance of differentiation and addressing customer needs
Importance of asking great questions and active listening
Consideration of compelling events and customer motivations in sales cadences
Importance of staying engaged with customers and providing relevant content
About Whitney Stowell:
Whitney Stowell is the CEO and Founder of Cribworks, a Washington, DC-based sales and business development consulting firm specializing in data-driven sales growth services.
With over 15 years of industry experience spanning commercial, startup, and government contracting, Whitney has held diverse roles in marketing, business development, corporate strategy, and government affairs.
Whitney's impressive career includes contributions to notable organizations such as Signify (formerly Philips Lighting), Major League Rugby's Old Glory DC franchise, Royal Philips, Elbit Systems of America, Chenega Corporation, and the United States Senate's Homeland Security and Governmental Affairs committee.
Beyond his professional endeavors, Whitney actively engages in community service. He serves on the Board of Directors for the Society of American Military Engineers (SAME) DC Post, addressing national security infrastructure challenges.
In the local rugby community, Whitney has been President of the Washington Irish Rugby Football Club and supports youth rugby clubs.
Additionally, he participates in various organizations in Washington DC, including the Smart Cities Group, Association for United States Army (AUSA), and USA Rugby.
Whitney holds a B.A. from Bates College in Maine and certifications in business development and capture management from Shipley University.
About Cribworks:
Cribworks is a dynamic startup consulting firm that guides businesses through the entire business cycle. As a client-centric and results-oriented business development consulting firm, Cribworks offers affordable, comprehensive services to meet the diverse needs of its clients.
Specializing in sales and business development consulting, the firm collaborates exclusively with clients to enhance their potential for success.
From tactical short-term engagements to strategic long-term positioning, Cribworks delivers tangible, actionable results that propel businesses in the right direction.
The firm provides a full spectrum of business development consulting services to local, state, national, and multinational clients, prioritizing delivering tailored solutions.
Cribworks emphasizes direct collaboration with clients on initiatives such as developing new and existing business opportunities, competitive intelligence, marketing strategies, and sound financial decision-making.
The firm is committed to fostering enduring partnerships, ensuring client businesses thrive and achieve their long-term goals.
With a personalized approach that recognizes each business's unique challenges and advantages, Cribworks stands steadfastly alongside clients today, tomorrow, and into the future.
Apply to be a Guest on The Thoughtful Entrepreneur:
https://go.upmyinfluence.com/podcast-guest
Links Mentioned in this Episode:
Want to learn more? Check out Cribworks website at
https://cribworks.co/
Check out Cribworks on LinkedIn at
https://www.linkedin.com/company/cribworks/
Check out Cribworks on Twitter at
https://twitter.com/whitneystowell
Check out Whitney Stowell on LinkedIn at
https://www.linkedin.com/in/whitney-stowell/
Check out Whitney Stowell on Facebook at
https://www.facebook.com/whitney.stowell.5/
Check out Whitney Stowell on Instagram at
https://www.instagram.com/whitney_stowell/?hl=en
Check out Whitney Stowell on Twitter at
https://twitter.com/whitneystowell
More from UpMyInfluence:
We are actively booking guests for our The Thoughtful Entrepreneur. Schedule HERE.
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Want to learn more about all the podcasts managed by UpMyInfluence? Opt in here.