The Human Cloud Podcast

Leaders, today we’re joined by Tyler Denk, Co-Founder and CEO of Beehiiv, one of the leading and fastest growing newsletter software companies. Beehiiv raised a $12.5 million Series A in 2023 and has been growing rapidly, with over $1 million in monthly revenue, according to Tyler.  In this episode, we’ll dig into why Tyler started Beehiiv, what led to their extraordinary success, and what’s next for Beehiiv and the solopreneur industry.   As freelance leaders, our roles often align more closely with those of founders than traditional employees. Whether you’re a VP leading a freelance program, a CEO of a talent platform, or a freelancer, we can all learn immensely from Tyler.  Key takeaways: 1: Founder market fit is the secret ingredient for entrepreneurial success, and can be defined by subject matter expertise. In Tyler’s case, his subject matter expertise came from his time growing Morning Brew as a leading newsletter. 2: Entrepreneurship never stops feeling like the house can fall at any time 3: Product management is tough to explain, yet crucial in growing a company. Being a good product leader means being able to be directionally correct, prioritizing the right roadmap, and tightening the feedback loop to iterate quickly based on informed insights rather than reacting to every piece of data.

Leaders, We know this past month has been fractional heavy. The reason is that fractional is rapidly taking hold across the US, Europe, and Asia. In this episode, John Arms discusses the rise of fractional leadership and its value in solving specific problems within organizations. John emphasizes the limitations of full-time positions and the decline of single job loyalty in today's workforce. John touches on the foundational requirements for being a successful fractional professional and how Voyageur University, a global leader in Fractional Talent education, helps Fractional professionals and businesses who hire them. We discuss the future of fractional work and the infrastructure needed to support it, as well as the centers of gravity in the fractional community. John emphasizes the shift towards value and problem-solving and the return of self-determination in the world of fractional work. Key takeaways: Fractional leadership provides specialized and flexible solutions to specific problems within organizations. Full-time positions often lack the necessary leadership and expertise to address complex challenges. The decline of single job loyalty and the rise of the solopreneurship has contributed to the demand for fractional leadership. Meetings are often unproductive and time-consuming, and fractional leaders can help organizations avoid unnecessary meetings. Incremental measures may not be connected to long-term impact in fractional work. The number of fractional professionals is growing rapidly, indicating a rising demand for their services. Markers for identifying successful fractional professionals include time in the market, wisdom, and a community mindset. The future of fractional work lies in the development of infrastructure and platforms that connect supply and demand. Fractional work emphasizes value and problem-solving over traditional employment models. Self-determination and the pursuit of freedom are key aspects of fractional work.

Leaders, Today we’re joined by Quentin Cloarec, Co-Founder and CEO of Trees Engineering, South East Asia’s leading Engineering Talent Platform. We discuss why Quentin started Trees Engineering, why clients are adopting their unique freelance model, and what leaders can learn from Quentin’s journey.  Quentin embodies two of the biggest trends in the freelance economy: The power of niche, specialized, freelance marketplaces; in his case an engineering talent platform. The global adoption of the freelance economy, with Quentin representing the growth of Southeast Asia and carrying these learnings into regions like the Middle East.    Key takeaways: Why Quentin went beyond a large, horizontal marketplace to solve his own problem within Engineering services How freelance adoption in South East Asia is mirroring the United States   How Quentin scaled their go to market  The value of being incremental versus the traditional view of disruption How large companies have embraced Trees Engineering Big wins, specifically how they enabled a Malaysian regional office to win business from HQ How it’s bigger than freelance, in his case, it’s about fixing the global energy crisis

Leaders, Karina Mikhli is a seasoned Fractional COO and the Founder of Fractionals United. Fractional is one of the most exciting aspects of the freelance economy. Instead of traditional, individual contributor freelance work, fractional unlocks executive level and strategic level engagements and professionals.  According to Human Cloud’s Industry Landscape, there are over 20 fractional focused solutions, spanning sales, marketing, and consulting.  Fractional is also global. The US seems to be first in terms of fractional adoption. But Europe and Asia are quickly catching up. In this episode, we’ll dive into everything fractional. We’ll define who fractional individuals are, what they do, how they differ from traditional freelancers, who they serve, how they work with clients, and what the future of fractional looks like according to Karina.   Key Takeaways: Growth of Fractional Work: The trend of fractional work is on the rise, with more professionals opting for fractional roles to leverage their expertise. Profile of Fractional Professionals: Typically, these individuals are experienced leaders who drive strategic initiatives and produce impactful results. Supportive Infrastructure: The fractional economy is supported by various platforms, marketplaces, and resources that facilitate the work of fractional professionals. Diverse Engagement Structures: Like freelance, fractional can take many different engagement structures. Importance of Communication: Effective communication and clear expectation-setting are critical for successful client engagements in a fractional capacity. Future Outlook: The future of fractional work is promising, with an expected growth in communities and associations dedicated to supporting fractional professionals. Get Involved: Future events and communities for individuals interested in fractional.

Leaders, Today, we have an exceptional guest, Rich Wilson, Co-Founder and CEO of Gigged.AI. Gigged.AI has been around for about three years, raising over $2 million, and is a fascinating use case as a technology-driven facilitator of freelance outcomes, differentiating from traditional marketplaces. In this episode, we dive into some key insights: 1. Technology as a Primary Driver: Gigged.AI stands out by making technology the core of their platform, which is not typical in the freelance space. For most platforms, technology plays a supportive role, but for Gigged.AI, it's the cornerstone of their success. Rich emphasizes that without their advanced tech, the company wouldn't exist. 2. Venture Funding: Unlike many freelance platforms that bootstrap and scale through the founding team, Gigged.AI needed venture funding. With three years of runway and two years dedicated to building their technology, venture funding was crucial for their survival and growth. 3. Enterprise Market Entry: Rich shares strategic insights on supporting enterprise accounts. Gigged.AI uses two specific strategies: enabling internal talent marketplaces and providing speed and customization for end users.

Leaders, In this episode, Henning Schwinum, Co-Founder and Managing Partner at Vendux, discusses the challenges and opportunities of fractional sales leadership. Vendux helps companies grow their sales leadership capital by matching you with a sales leader and team necessary to transform your sales strategy. Henning brings a unique, process-oriented approach to sales leadership. This episode is not just about hiring freelancers; it's about fundamentally transforming your organization and driving growth through efficiency. He shares insights on scoping engagements, the business model, and the success of fractional executives. Henning also addresses common objections and defines the space between fractional and freelance work. He highlights the importance of industry expertise and the value of fractional sales leaders in small to mid-sized companies. Henning also discusses the benefits of external expertise and the limitations of full-time employees in certain scenarios.

Leaders, it’s no secret that Enterprise adoption is tough. Specifically, enabling large companies to scale their freelance spend similar to how external talent is already over 50% of talent within most companies. It’s also getting increasingly blurred with the existing external talent ecosystem. Leaders face tough questions, such as, should external talent programs be different from freelance talent programs? Should talent platforms integrate with VMS and MSP suppliers? Is freelance competitive, or complementary to the contingent talent space? Today we have Colin McDonagh, is a 10+ year veteran in helping large companies scale external talent programs. He is our go-to when it comes to the evolution of external talent, and how freelance is the same, or different from the existing external talent ecosystem. Colin recently joined Worksome as their Head of Enterprise Workforce Strategy.  Colin has extensive experience with successful contingent talent brands. He has served as Global Program Manager for contractor programs at Meta, formerly Facebook, Director at Allegis, helping clients such as Microsoft, and as an advisor at Utmost, which was acquired by Beeline in 2022. He’s also been an early champion of innovative solutions like direct sourcing.  Key takeaways: 1: Where does freelance sit within the greater external talent ecosystem 2: What’s the difference between freelance and gig, freelance and contingent, and can freelance work within the confines of contingent talent   3: Why aren’t we as far along as we thought we’d be 10 years ago  4: Why aren’t there internal freelance roles when companies are spending over $2 trillion dollars globally on freelancers

Leaders,  We all know Enterprise adoption is the biggest barrier facing the freelance economy today. While freelance as a talent source is globally recognized, we’re still in the first inning of the maturity of freelance as an industry. Unlike Uber or other B2C based startups, freelance as an industry looks more like a B2B professional service transformation than a venture backed technology industry. The impact is that instead of overnight adoption, industry maturity is a long, mostly linear process.  Which is why today’s guest is so perfect.  Jeff Fenigstein has scaled marketing freelancers across marketing teams for large companies. First at Woodruff Sawyer, and now as the founder of Market Growth. Specifically, Jeff knows how freelance can be a strategic sourcing strategy that creates dream teams rather than looking at freelancers as transactional contractors that “plug a hole” or “fill a gap”.  In this episode, we’ll get into why Jeff turned to freelance, what his use cases were, and how he overcame the organizational bureaucracy that stands in the way of so many freelance leaders. He also shares his experiences with freelance adoption in different environments, such as startups and enterprise organizations. Jeff emphasizes the need for internal champions and effective communication to overcome hurdles and successfully integrate freelancers into an enterprise. He recommends that enterprise leaders explore freelance platforms, try small projects, and educate themselves on the benefits and possibilities of freelance work. Key takeaways: Freelancers can help businesses accomplish more and reach their goals by providing specific skills and capacity when needed. Using freelance platforms offers access to top talent, faster hiring processes, and the ability to try before committing to a long-term hire. Freelance adoption is different depending on the environments, such as startups and enterprise organizations.  In the Enterprise, freelance adoption requires internal champions and effective communication. To get started, Enterprise leaders should try small projects.

Leaders,In this episode, Jonathan Wolfson, Chief Legal Officer and Policy Director at the Cicero Institute, comprehensively analyzes the freelance economy from legal and governmental perspectives. As we all know, compliance is a massive blocker in adopting freelancers at scale. Jonathan breaks down the policy side of how legislation is influenced, formalized, and leads to compliance regulations. While Jonathan is based in the US, understanding the forces of freelance legislation is applicable globally.More than today’s current legislation, Jonathan will also outline the history of employment law, which was established in the 1940s and does not accommodate today's modern workforce. From this historical perspective, we’ll understand the government's opposition to freelancing.Last, Jonathan will highlight the challenges and opposition to freelancing, the risks and liabilities for businesses, the impact on business transactions, potential solutions and future outlook, the legislative landscape and regulatory changes, and actions individuals can take to make an impact.Key takeaways:  Legislative and regulatory changes are necessary to address the challenges of independent contracting, though the future remains uncertain Current employment laws, dating back to the 1940s, fail to address the modern freelance economy Misconceptions, political motivations, and concerns about tax collection and worker protection fuel opposition to freelancing Businesses face significant risks and liabilities if workers are misclassified as independent contractors

Leaders, the freelance economy is quickly growing from a marketplace dominated industry to a robust ecosystem with 10 different segments.  One of the most fascinating segments is the freelancer focused tools and solutions that enable freelancers to scale their businesses without needing a platform, or in tandem with a platform.  Upside is one of these exciting new startups leading the solopreneur charge. By monetizing referrals, Upside enables freelancers, consultants, solopreneurs, whatever you want to call us, to monetize our network in a way that’s a win-win for us, our clients, and Upside.  In this episode, we’ll open up the hood to why Mike is building Upside, how he got to the insights of starting Upside (hint…he has been in this space for a while), and where he sees the freelance economy going.   You will also meet an incredible founder, Mike Wilner. Before Upside, Mike built a freelance web design marketplace in 2015, Co-Authored the book Oversubscribed, and worked at Amazon Web Services.  Key takeaways: Traditional marketplaces face challenges in retaining top talent and generating demand. Upside is a partnership platform that empowers individuals and small firms in the professional services industry. Successful referrals are the core metric for Upside, enabling users to share opportunities and collaborate. The future of the freelance economy lies in uncapping the potential of individuals and creating infrastructure for collaboration and business development.