21st Century Entrepreneurship

Blake Reichenbach is a Product Manager at HubSpot, focusing on the Content AI Platform, and the founder of Howdy, Curiosity, an innovative online nonfiction bookstore and learning community. With a rich background in higher education, marketing, and the SaaS industry, Blake brings a wealth of expertise and a unique perspective to his roles. His professional journey at HubSpot has been marked by leading pivotal initiatives such as the modernization of Trust and Safety infrastructure through advanced machine learning integrations while managing multiple high-priority corporate objectives.In our conversation, we explored the nuanced challenges and triumphs of nurturing entrepreneurial endeavors alongside a career. Blake shared insights from his journey, emphasizing the lack of support for non-traditional, part-time entrepreneurs. "There weren't ways for people like me to connect with mentors and to connect with other people who had been down the path I was going down," he explained, highlighting the initial isolation he felt.The discussion also touched on the transformative potential of combining professional stability with entrepreneurial passion. Blake detailed his evolution from a discontented academic advisor to a fulfilled product manager and side-project entrepreneur. His transition was not just a career change but a complete lifestyle overhaul, facilitated by strategic learning and creative exploration. "I knew nothing about building my own business...and really, the only skill set that I had relevant to my entrepreneurial journey at that time was the skill set I was using as a writer," Blake recounted, illustrating the humble beginnings of his entrepreneurial path.Blake is particularly passionate about fostering a community that supports "the curious professional." He has created Howdy, Curiosity, a platform designed to cater to those balancing full-time jobs with creative and entrepreneurial projects. This initiative aims to build "support and accountability systems for folks who are working on creative and entrepreneurial projects in their free time."His journey underscores that entrepreneurship doesn't always require risking everything. It can be a stable, incremental pursuit that complements an existing career. "It's the projects we pursue on the side that are the most rewarding and can lead to the most significant long-term growth for ourselves, both personally and professionally," he shared, providing a fresh perspective on what it means to be an entrepreneur today.Key Takeaways:Entrepreneurship as a Part-Time Pursuit: The conversation sheds light on the often overlooked path of part-time entrepreneurship, proving that one can pursue entrepreneurial ventures without giving up the stability of full-time employment.The Value of Community: Blake emphasizes the critical role of supportive communities for part-time entrepreneurs, illustrating how such networks can provide the necessary resources and mentorship to thrive.Leveraging Corporate Skills for Personal Projects: Blake's journey demonstrates how skills acquired in a corporate setting can be effectively translated into managing and growing personal projects, enriching both professional and personal aspects of life.Listeners will leave this episode inspired by Blake’s resilience and innovative approach to entrepreneurship, equipped with practical insights into balancing passion projects with professional responsibilities.

Elizabeth Eiss is a seasoned entrepreneur and an advocate for small businesses and solopreneurs. In our conversation, we explored the crucial role small enterprises play in the economy and the unique challenges they face. Elizabeth shared her insights on how small businesses can leverage the gig economy to scale effectively, optimize operations, and maximize their impact. "Small businesses are the backbone of... economies," Elizabeth points out, emphasizing the profound influence they hold over national productivity.A significant portion of our discussion revolved around the potential of freelance talent to transform small business operations. Elizabeth's approach is not just about filling gaps but strategically enhancing business capabilities. "We're really looking for small businesses that understand the value of their time," she explains, advocating for a shift from do-it-yourself to expert-driven processes that ensure reliability and quality.Elizabeth also provided a personal perspective, linking her experiences as a breast cancer survivor to her professional ethos. This profound personal journey underscored her belief in the importance of valuing time, both personally and professionally. "Free time is an important objective, too, not just doing more for your business," she reflects, highlighting the balance between work and life that many entrepreneurs strive to achieve.Key takeaways from this episode include:The strategic use of freelancers can enable small businesses to focus on core competencies and growth.Building reliable relationships with pre-vetted talent can streamline operations and reduce overhead.Personal challenges, like health crises, can profoundly influence professional perspectives and operational strategies.Listeners will come away with a deeper understanding of how small businesses can navigate the complexities of modern work environments, leveraging freelance talent for scalability and efficiency. Elizabeth's insights are a beacon for solopreneurs and small business owners looking to transform their operations and achieve sustainable growth.

Joe Blackburn is a seasoned entrepreneur with a history of successful businesses built through word of mouth, and we spoke about the profound impact this traditional yet underutilized technique has on sales and business growth. Joe shares, "I teach people how to become deadly at sales by mastering word of mouth," emphasizing the necessity of trust and authentic connections in the sales process.During our conversation, Joe underscored the limited effectiveness of relying solely on systems and processes without the foundational human element. He explains, "We're all in the people business," and introduces his unique approach, the PILLAR system, which is designed to leverage personal relationships to advance business goals. His straightforward philosophy cuts through the noise: "There's no way in there because I don't deal with assholes, and you shouldn't either."Joe's insights extend beyond sales strategies. He reflects on personal growth and risk-taking, sharing poignant moments from his own leap into entrepreneurship, which was driven by a desire for a more fulfilling life despite significant personal challenges. "Once you actually take that leap, all kinds of opportunities present themselves," Joe remarks, illustrating the potential rewards of stepping out of comfort zones.Furthermore, Joe discusses the critical role of mindset in achieving long-term success. He believes that "80% of your success is going to be psychological," stressing the importance of mental strength and resilience over mere technical skills or business acumen.Listeners can expect to walk away with a deeper understanding of:The power of word of mouth in building trust and credibility.The necessity of aligning personal values with professional interactions.How personal transformation and risk-taking are integral to business success.Joe's approach to sales and business is a blend of traditional wisdom and innovative strategies, making this episode a must-listen for anyone looking to enhance their influence and success in today's competitive market.

Ayat Shukairy is a seasoned expert in conversion rate optimization (CRO) and the co-founder of a renowned CRO company and tool. In our conversation, we delved into the intricate world of CRO, exploring its fundamental importance in transforming site visitors into loyal customers. Ayat illuminates the often-overlooked aspects of customer engagement and conversion, asserting, "It is about trying to create a better, more user-friendly, and persuasive experience on your site."From her initial career shift from teaching to marketing, Ayat's journey underscores the transformative power of understanding and influencing consumer behavior. She explains, "I was completely blown away by the whole entire concept" of persuading site visitors to engage more deeply, highlighting the evolution of her career into a CRO specialist.Key topics discussed include the nuances of optimizing the visitor experience, the importance of aligning landing pages with customer expectations, and the strategic use of analytics and user research. Ayat stresses the critical role of A/B testing in validating changes on websites to ensure they enhance conversion rates. "Making changes without testing means that you don't know the actual impact that change had on your bottom line," she notes, emphasizing the scientific rigor required in CRO.Listeners will glean insights into the broader implications of CRO beyond mere technical tweaks, understanding its role as a bridge between traffic acquisition and customer retention. Ayat also shared her passion for educating and empowering others, drawing from her teaching background to enhance her approach to customer engagement and business strategy.Takeaways from this episode include the importance of:Understanding the visitor's journey to improve site interaction.Employing A/B testing to confirm the effectiveness of site modifications.Crafting a user experience that aligns seamlessly with marketing messages.By integrating these elements, businesses can significantly boost their online engagement and conversion rates, turning casual browsers into committed customers. This episode is a treasure trove of actionable advice for anyone looking to enhance their website's effectiveness and convert traffic into tangible success.

Justin Cooke is a founder with an extensive background in creating and scaling online businesses, and we spoke about his journey from starting a small outsourcing company in the Philippines to running Empire Flippers, a prominent online business brokerage. His entrepreneurial path is marked by bold decisions and strategic shifts, reflecting a dynamic approach to business challenges and opportunities.Justin candidly shared the trials and triumphs of his entrepreneurial journey, noting, "We went from just the two of us with a small Philippines team to selling nearly $500 million worth of websites and online businesses." This transformation showcases not only growth but also the resilience required to pivot from initial setbacks. He explained the early days of their venture, where an outsourcing failure led to an unexpected yet prosperous pivot: "So when they started cutting back on us, we said, what the hell are we going to do? How are we going to make money? How are we going to survive out here?" This moment of crisis spurred the creation of niche websites, a move that catalyzed their success.The evolution of Empire Flippers from a provider of niche websites to a thriving marketplace for buying and selling online businesses illustrates a key entrepreneurial lesson: the power of listening to your market. Justin emphasized the importance of adapting to customer needs, stating, "We realized there's a market for these people were interested in buying these small websites." This insight led them to expand their services, fundamentally shifting their business model to include brokering for external clients, thereby magnifying their market impact.Another significant discussion point was the cultural shift towards remote work, which became a cornerstone of their company culture. Justin reflected on this transformation with personal insight: "Even after this, this is 2010, 2011... and I stayed in the Philippines and kind of worked from home." His embrace of remote work predated the global trend, highlighting a forward-thinking approach that benefits both the company and its employees.For aspiring entrepreneurs, Justin’s experiences offer valuable lessons. His advice underscores the importance of bold action and the willingness to embrace responsibility for growth: "It took us a long time to hire that first foreign hire... You're taking on someone else's responsibility. You're putting extra expense on the business. Why don't we just keep that money for ourselves? But you limit your growth when you're not adding people."Listeners will leave this episode with a deep understanding of the challenges and rewards of entrepreneurship, the strategic value of adaptability, and the transformative potential of listening deeply to customer needs. These insights are not just strategies but are foundational principles that can guide new business ventures towards success.

Danny Nathan, founder and CEO of Apollo 21, is a seasoned innovator with deep roots in the venture building and technology space, and our conversation explored the complex landscape of corporate innovation. We discussed why fostering true innovation within established companies is notoriously challenging and what can be done to overcome these hurdles.Danny opened up about the rigid operational frameworks that often stifle innovation, explaining, "Innovation is hard today because organizations as they grow up get stuck in the mindset of focusing on what's working today at the expense of what might work tomorrow." He underscored the necessity of embracing risk and exploration, which are vital for long-term success but are often sidelined in favor of short-term efficiency and risk aversion.One of the most poignant themes of our discussion was the concept of 'customer development'—a core process at Apollo 21. Danny stressed the importance of this approach by saying, "The more we talk to our customers, the more we find opportunities to understand what their pain points are." This customer-centric strategy not only identifies existing gaps but also aligns innovations with genuine user needs and anticipates future demands.Our talk also covered striking examples of missed opportunities by major companies, which highlighted the dangers of complacency in business. Danny posed reflective questions like, "Why didn't Blockbuster create Netflix?" and "Why wasn't Airbnb created by Hilton, or Hyatt, or the Marriott?" These examples illustrate how traditional companies often overlook transformative opportunities due to their entrenched ways of thinking.From the episode, listeners can draw several key takeaways:Innovative Mindset: Shifting from a purely efficiency-driven approach to one that values exploration and learning can unlock new possibilities.Customer Integration: Deeply engaging with customers to understand their current and future needs is crucial for relevant and successful innovations.Process-Driven Innovation: Implementing structured processes that allow for iterative learning and gradual scaling can facilitate more sustainable and impactful innovation.In conclusion, Danny Nathan's insights remind us that innovation is not just about new ideas but about transforming these ideas into reality through strategic foresight and customer engagement. As Danny put it, "We are focused heavily on finding the smallest thing that we can create alongside our partners that will drive the most value for you and your customers in the shortest period of time." This approach not only fosters immediate impact but also builds lasting customer loyalty and positions companies for future success.

David Jones is the founder and CEO of MRSA Talent Enterprise, and we spoke about the dynamic interplay of technology and career development. As someone at the helm of innovation in talent assessment, David discusses the seismic shifts in how careers are built and talents are assessed in today's fast-paced, technology-driven work environment. "We're really at an inflection point," he notes, highlighting the transformative power of technological tools in both individual career trajectories and organizational growth.The episode dives deep into the evolution of the talent assessment industry, influenced heavily by technological advancements like AI. David reflects on how these tools not only enhance the process of identifying and nurturing talent but also ensure that labor markets become more efficient. "Using really robust and statistically stable and standardized tools helps employers to understand who would be the best candidates," David explains, emphasizing the critical role of quality data in optimizing talent placement.We also explore the broader implications of these changes for entrepreneurship. David points to how modern assessments can predict entrepreneurial success, noting, "We're able to find from all the tens of thousands of entrepreneurs who've taken our assessments are some of those characteristics, behaviors that help to predict who would be most suited to a career or to running a business as an entrepreneur." This insight is particularly valuable in a world where the spirit of entrepreneurship is more vibrant than ever, with many aspiring to make their mark independently.Further, David shares personal reflections on his journey, revealing that competitiveness and a passion for fitness have been his personal drivers, while stressing the importance of collaborative teamwork in fostering a healthy, productive business environment. "I think for me, personally, working with a team and working with colleagues who have complementary, sometimes quite different skills and viewpoints can be really beneficial," he states, underscoring the synergy that diverse teams can create.This episode provides a rich pool of insights into how technology and modern methodologies are shaping not just the future of work, but also the future of worker evaluation and development. Whether you're a HR professional, a budding entrepreneur, or somewhere in between, there's a wealth of knowledge here to help navigate the evolving landscape of work.

Greg Mohr is a seasoned entrepreneur and franchise consultant, and we spoke about the fascinating world of franchising versus starting a privately owned business. Throughout the interview, Greg shared insights from his personal journey transitioning from a corporate engineer to a franchise consultant, revealing the complexities and rewards of each path.Greg candidly discussed the pros and cons of franchising compared to launching and managing a private business. He reflects on his initial ventures, stating, "I didn't know a thing about dry cleaning, and I didn't have anybody to turn to. It's our business. We could do whatever we wanted with it, got all the money for it." This highlights the autonomy and potential financial rewards of privately owned businesses but underscores the steep learning curve and risks involved.In contrast, franchising presented a structured path with robust support systems. Greg appreciated the pre-existing frameworks that helped him navigate the business landscape more effectively: "They have a plan of action, so they have a plan of action for me. Do this, do this, do this. They've already gone through all the hurdles. They've already made all the mistakes." The episode delves into how franchises can accelerate the journey to success, with Greg noting, "You're really looking to have that franchise get you there to where you want to be two to three years quicker than if you were to do it yourself."Listeners can also gain valuable insights from Greg's experience with franchise consultants, who helped demystify the process and set realistic expectations. "The franchise consultant said, whoa, let's put your brakes on all that. Take a step back and let's look at, where have you been?" This advice underscores the importance of careful, informed decision-making in franchising.Moreover, Greg discusses the importance of due diligence when exploring franchise opportunities, emphasizing the need to understand the franchise disclosure documents and speak with current franchisees. He advises, "You want to make certain that you talk to as many as possible. 10, 15, 100, whatever you have time for."Key takeaways from the episode include the importance of understanding both the financial and operational aspects of franchising, the value of expert guidance in navigating the franchise landscape, and the critical role of self-reflection and suitability when considering entrepreneurship.Greg's journey and insights provide a rich resource for anyone considering the franchise route, illuminating the path with real-world examples and practical advice. Whether you're an aspiring entrepreneur or a seasoned business owner, this episode offers a deep dive into what it takes to make informed decisions in the dynamic world of business ownership.

Alex Neist is a former athlete turned serial entrepreneur, and we spoke about the dramatic shifts in his personal and professional life that led to profound self-reflection and eventually, groundbreaking innovation. Through a candid recount of his experiences, Alex shares how hitting rock bottom was not the end but a pivotal beginning. "Six years ago, I thought I had everything... And then two years after that, I lost all of it," Alex reveals, setting the stage for a discussion on resilience and reinvention.Central to our conversation is the theme of recovery, not just in business, but in personal health and relationships. Alex emphasizes the importance of sleep as a cornerstone of recovery, which ultimately led him to a surprising discovery that changed his life. "The one of the first things I started to look at was my sleep, which led me to this company that we founded now," he explains. This journey into the world of sleep improvement illustrates how personal challenges can lead to professional opportunities.Alex also touches on the emotional and physical toll of entrepreneurial life, particularly how neglecting personal relationships can spiral into larger life crises. His personal story is a stark reminder of the interconnectedness of our well-being and our work. "I was ignoring my wife and my kids, and then it just all kind of spiraled out of control from there," he shares, highlighting the critical balance needed between work and home life.From his narrative, listeners can glean insights into the mindset of overcoming adversity and the relentless pursuit of solutions that define entrepreneurial success. Alex's approach to business and life is encapsulated in his advice, "look around you and look for problems... because some of the best businesses are businesses that are solving a problem." His reflection on past ventures and the evolution into his current success story provides a blueprint for transforming personal setbacks into professional victories.The episode is packed with lessons on resilience, the science of sleep, and the art of brand creation, making it a rich resource for anyone looking to understand how to turn life’s low points into platforms for innovation. Alex's story is not just about the rise, fall, and rise again of a businessman but about how a deep dive into personal health can lead to the most significant professional breakthroughs. As we explore his journey, we uncover the essential elements of bouncing back stronger and the impact of self-care on achieving sustainable success.

Jeff D. Standridge, Managing Director of Innovation Junkie, brings a wealth of experience as an accomplished entrepreneur and venture capitalist. Our conversation explored the valuable insights he has derived from his extensive and varied career. From his early academic challenges to becoming a corporate executive and influential mentor, Jeff illustrates that "failure is only failure if you quit, otherwise it's just feedback."Throughout the interview, Jeff shares his journey from a small-town upbringing to international business success, emphasizing the importance of resilience and adaptability. He recounts his transformative experiences, saying, "I spent about 20 years as a corporate executive...and that's really what led me into the world of entrepreneurship and venture capital investing." His stories underscore the significant impact of embracing setbacks as learning opportunities, a theme he passionately advocates.Jeff also dives into the principles that have guided his approach to business and leadership. He discusses the "culture of excellence" that sustained companies foster, which revolves around strong leadership, clear organizational focus, committed team engagement, empowering communication, complete accountability, and organizational agility. This framework, Jeff explains, is essential for any organization aiming to achieve strategic and sustained growth.Moreover, Jeff touches on his literary contributions, which aim to guide and inspire entrepreneurs. His books like 'The Innovator's Field Guide' and 'Top Performers Field Guide' offer reflective questions that encourage deep thinking about innovation and performance. He reflects on the dual importance of results and relationships: "If we are so focused on the delivery of results at the expense of relationships, we will be wildly successful very quickly until we alienate everyone around us."In addition to business, Jeff shares personal reflections, stressing the importance of balance and prioritizing family. He advises, "Business is a means to something. It's not the end in and of itself," emphasizing that personal relationships should not be sacrificed for business success.Listeners will leave this episode with a deeper understanding of how setbacks can be reframed as stepping stones to success, the critical elements of creating a culture of excellence in any organization, and the importance of maintaining balance between professional ambitions and personal life. Jeff's journey and insights are a testament to the power of perseverance and the potential for personal and professional transformation.