Gretchen Leslie: How To Build a Lean, Mean, Multimillion-Dollar Team - Part 1

In our final episode of the Creator COO podcast, this week, Matt sits down with Ben Burns, COO of The Future, an educational platform dedicated to empowering creative professionals worldwide. Ben shares insights into The Future's transformative journey from content creation to a comprehensive educational entity, the introduction of innovative tools like 'DoBot' for AI-powered coaching, and the evolution of their team to support the company's growth.  In this episode, we explore the intersection of creativity, education, and technology with Ben Burns. The Futur, at its core, strives to help individuals make a living doing what they love, aiming to reach a billion people. Ben details the strategic shift from a personality-driven brand to a broader educational platform, the challenges of marketing, and the importance of adapting and evolving in the ever-changing creator economy. Dive into the details of building a successful platform that balances educational content, community engagement, and innovative technology to create a sustainable business model that not only generates revenue but also significantly impacts its users' lives. Jump into the Conversation: 13:32 - The mission and vision behind The Futur 15:21 - The evolution of The Futur from content to commerce 18:36 - Building the team to support The Futur's growth 22:06 - Shift towards genuine content creation 25:58 - Changes in The Futur's team over the years 29:07 - Integrating AI into coaching with 'DoBot' 33:57 - Ben's role in realizing Chris Do’s vision 36:45 - Transitioning to a publishing model and expanding the brand beyond Chris Do 49:30 - Launching the Accelerator Membership for deeper engagement Continue the conversation with these resources: Check out The Futur Connect with Ben Burns on LinkedIn and Twitter

This week, Matt engages in a deep dive with Zach Miller, delving into the intricacies of navigating the creator economy and scaling a content-driven business like Bucket Squad. Zach, with his rich background spanning from McKinsey to Spotify, and now pivotal in steering Bucket Squad's growth trajectory, shares invaluable insights into the strategic thinking, operational challenges, and the evolving landscape of content creation and distribution. In this episode, we unravel the dynamics of content creation businesses, exploring the balance between organic growth and strategic mergers & acquisitions, the nuances of diversifying talent and content to ensure sustainable growth, and the critical importance of aligning new ventures with core audience interests and creator passions. Join us as we dissect the operational complexities of scaling in the creator economy, the strategic considerations in expanding business models beyond traditional content creation, and the profound potential of creators in shaping the future of media and entertainment. Jump into the Conversation: 3:24 - Organic Growth vs. M&A in expanding the business 8:07 - Exploring opportunities beyond podcasting for Bucket Squad 13:15 - Strategies for diversifying talent and content 19:02 - The challenge of operational scaling and strategic planning 24:36 - Financial models and business strategies for growth 30:41 - Dynamics of the creator economy and its impact on media 35:59 - The critical role of belief in driving success and strategic bets 41:33 - Operational and strategic nuances in creator-led businesses 47:25 - Reflecting on the potential of creators to build monumental businesses 52:48 - Zach's personal insights on transitioning from consulting to the creator economy Continue the conversation with these resources: Connect with Zach Miller on LinkedInExplore Jesser and Bucket Squad’s content and products

This week Matt is joined by Natalie Barbu, a content creator, podcast host, CEO and founder of Rella a SaaS business created to be the ultimate project management assistant for creators. She has built a following of over 380,000 on her personal channels, raised an impressive $1M in pre-seed from top investors, and grown revenue by 35% month over month since launching the business.  In this inspiring episode, we dive deep into the world of content creation, entrepreneurship, and the ever-evolving creator economy with Natalie Barbu, content creator, podcast host, and CEO of Rella. Rella is a pioneering software business crafted to serve as the ultimate project management assistant for creators, addressing the glaring need for a more integrated and efficient approach to managing the multifaceted demands of content creation. Join us as Natalie shares her personal journey from starting on YouTube over a decade ago to identifying a gap in the market and taking the bold leap to fill it with Rella. We explore the challenges and triumphs of building a software business in the creator economy, the importance of aligning team dynamics with the creative vision, and Natalie's insights into the future of content and business. Jump into the Conversation: 02:15 - Natalie’s evolution from content creator to CEO of Rella 05:40 - The unique challenges faced in establishing a software business  09:25 - Building a supportive team, emphasizing the need for alignment and a positive work culture 13:50 - The critical role of content in business today 18:00 - Early days on YouTube and seeing a gap in the market  22:45 - Potential opportunities for businesses catering to creators, and the future of creator-led ventures 27:10 - Advice for creators considering entrepreneurship and getting feedback 31:55 - Rella's ambitions and comments on the creator economy  Continue the conversation with these resources: Check out Rella Follow Natalie on Instagram and YouTube Listen to the Real Reel podcast

You hired a new member of your small-but-mighty team. But it’s a few months in and something feels…off. How do you know if it’s time to part ways, or if it’s a coachable situation? It all starts with your organization’s values.  In part two of our conversation, Gretchen Leslie, President of I Will Teach You to Be Rich, who successfully leads a multimillion-dollar company with just nine people, shares her secrets to hiring individuals that perfectly reflect her company's core values.  We dive deep into Gretchen's values-based interview process, her tips for treating candidates well to set the right organizational tone, and the importance of clarity in defining roles. She explains how to set new hires up for success with precise plans for their first 90 days.  Gretchen also emphasizes the importance of feedback within business partnerships. She shares why meditation is crucial for processing feedback and explains how to respond to criticism without losing your cool. Here are the key takeaways from our conversation with Gretchen: Hire for Values: The secret to massive growth with a lean team is hiring individuals aligned with your core values. Gretchen shares how she embeds her values into every part of her company, starting at the interview stage. This approach ensures that you bring on team members who are not just skilled but also passionate advocates of your brand ethos. Foster Growth Through Feedback and Reflection: Gretchen shares her tactics for integrating constructive feedback and self-awareness into your growth strategy. She explains the importance of giving and receiving feedback that respects the creative process and the emotional context of the individuals involved. She discusses her 1-10 feedback scale to gain more nuanced insights and her meditation tips for processing feedback without losing your cool. Forge a Clear Path for New Hires’ Success: Gretchen explains how to set new employees up for success in their first 90 days. She shares about identifying specific markers to hit at 30, 60, and 90-day intervals. Implementing a structured onboarding process empowers new team members with clarity and direction, allowing them to contribute to your business quickly and effectively. Leslie shares how this approach has enabled her nine-person team to surge to multimillion-dollar growth. Jump into the Conversation: [02:09] Connecting organizational values and actions [09:40] Starting the hiring process with specific role objectives and clear success metrics [15:29] Assessing candidates’ fit with test projects [21:43] The importance of frequent, informal feedback [30:16] Responding to feedback without losing your cool [44:00] Gretchen’s recommendations for finding a stellar operational partner Continue the conversation with these resources: Follow Gretchen Leslie on LinkedIn Read Traction and Rocket Fuel by Gino Wickman Reach out to EOS Worldwide for integrator recommendations

There’s a danger every creator faces in scaling their business: doing it too fast.  Today’s guest has the ultimate experience in scaling in revenue, but keeping her team lean and profitable. Gretchen Leslie, President of I Will Teach You to Be Rich, is reinventing the way small and mid-sized companies think about growth. In this episode, Gretchen shares her secrets to running a lean, mean multimillion-dollar team with just nine people. She shares how creator businesses can scale even in the face of financial constraints. She explains when to hire full-time vs. when to lean into fractional hiring, and the benefits of leveraging off-the-shelf SaaS tools instead of reinventing the wheel. Gretchen also opens up about her personal style and her journey from corporate roles to the thriving creator economy. She offers practical advice to optimize the integrator-visionary relationship, encourage open communication, and diagnose business problems. Show Notes: Here are the key takeaways from our conversation with Gretchen: Embrace Strategic Leadership Over Daily Operations: Gretchen advocates for removing barriers so your talented team can excel. She offers a roadmap for creators to rise from day-to-day nitty-gritty to providing visionary guidance. Her consultative role at Wolf and Company demonstrates the power of diagnosis before action—crucial for creators looking to evolve from being practitioners to strategic leaders. She encourages Creator COOs to shift their mindsets from micro-management to macro leadership, cultivating an environment where both creativity and structure thrive. Leverage Fractional Talent & SaaS Solutions for Growth: Gretchen shares advice for scaling your business even with financial constraints. She explains the pivotal role fractional COOs can play in diagnosing business needs and spearheading strategic hiring, allowing creators to focus on their vision and creative output. She also recommends leveraging SaaS solutions to avoid reinventing the wheel. She shares practical tips for growing your business in a sustainable way while prioritizing profitability, and finding support through networking and trusted industry recommendations. Pinpoint Your Needs with Jobs to Be Done: Gretchen introduces the Jobs to Be Done framework, a technique for pinpointing your business’s operational needs. This approach encourages you to think beyond job titles and focus on the specific tasks and outcomes that your business requires. By categorizing operations based on what 'job' needs to be accomplished, you'll be able to identify the skills and support your organization truly needs. Jump into the Conversation: [02:00] Gretchen’s experience in the creator economy [10:25] Leveraging existing resources vs. building your own [17:15] Using the jobs-to-be-done framework to determine when to hire an integrator [26:39] Fostering integrator-visionary relationships [30:30] Saying “yes” to visionary ideas [39:18] Diagnosing culture problems in companies Continue the conversation with these resources: Follow Gretchen Leslie on LinkedIn Read Traction and Rocket Fuel by Gino Wickman Reach out to EOS Worldwide for integrator recommendations

There’s a secret to hiring and retaining the best talent in the creator space…and it’s probably not what you’d expect!  In this conversation, Vouch’s Marty Pesis, discusses the art of building and nurturing a pipeline of talent worth hiring–well before you’re ready to open that job posting. His secret ingredient? Employer branding. He shares his tips for making sure you’re selling your team and its culture just as much as selling your creator. And for Marty, hiring is a science just as much as an art. He outlines his methodology that will help you stay ahead of the hiring game, even in this competitive market.  Key Takeaways: Embrace a Passion-First Approach in Hiring: Marty makes a case for hiring individuals who not only possess the necessary skills for the job but are also deeply passionate about your brand. He shares insights on how harnessing the enthusiasm and dedication of such talent pays off in the long run. Hard skills are important, but in the early days of a creator business, passion is even more crucial. Develop a Structured Yet Tailored Hiring Methodology: Marty outlines four steps for effectively finding and hiring top talent: promoting the job, screening applicants, conducting paid sample projects, and initiating a trial phase. This approach allows qualified candidates to showcase their skills and experience a day (or week) in the life of the role they’re exploring. Teams can tailor this approach to their specific needs, ensuring they assess the most important skills as well as cultural fit. Focus on Employer Branding to Attract and Retain Top Talent: Marty emphasizes the significance of a strong employer brand in attracting top talent. He shares practical steps creator businesses can take to enhance their employer branding, such as maintaining transparency in the recruitment process, managing the candidate rejection experience with care, and concertedly building a positive culture. Jump into the Conversation: [03:23] Marty’s journey into the creator economy [13:38] Solving the talent access bottleneck [23:01] The importance of employer branding in attracting top talent [32:50] Leveling up the recruiting experience with a four-step funnel [44:23] Rejecting candidates with empathy [53:27] The people management responsibilities of a Creator COO [01:02:57] Compensating Creator COOs competitively  [01:07:10] Marty’s top pieces of advices for winning top talent [01:11:29] The best time to bring in a Creator COO Continue the conversation with these resources:Follow Marty Pesis on LinkedIn

Most creators are missing basic financial literacy that could ruin their business. Eric Wei is making it his mission to fill that gap. Today's conversation with Eric, Co-Founder of Karat Financial, the black card for content creators is a glimpse into how he’s doing just that. Eric and his team have raised over $30 million from Union Square Ventures and Y Combinator, as well as from top creators such as Graham Stephan, Nas Daily, and Josh Richards.  In this episode, Eric explains the unique financial literacy challenges faced by creators and the need for business financial education. We discuss navigating co-founder dynamics, scaling creator businesses, and the importance of financial management and operational partnerships in the creator economy. Ready to learn? Let’s dive in. Here are the key takeaways from our conversation with Eric: Embrace the Power of Delegation and Trust As a creator, scaling your brand means acknowledging that you can't handle every aspect of your business alone. Eric Wei dives deep into why finding a trusted COO can be a game-changer. By learning to delegate, you can focus on what you do best—creating content—while an operational partner manages the growth challenges. Eric shares real-life examples of successful partnerships and gives advice on aligning business expectations and establishing trust. Financial Literacy is Key to Business Longevity Don't let your passion for content creation overshadow the importance of financial management. Eric shares crucial financial literacy tips for creators and Creator COOs, such as budgeting for uneven cash flows and the pros of transitioning from a sole proprietorship to an LLC or S corp. Eric provides insights into tax benefits, protecting personal assets, and wise investment strategies to secure your business's future. He warns against avoiding common pitfalls and explains how to set up a sturdy financial infrastructure for your creative enterprise. Diversify Your Revenue Streams for Stability Relying solely on ad revenue or unpredictable brand deals can make your creator business financially vulnerable. Eric highlights the benefits of diversifying your revenue with memberships, products, and deeper audience engagement strategies. He explains both the challenges and opportunities in creating consistent, loyal fan bases, particularly for short-form content creators looking to branch into long-form material. By adopting the right revenue model, creators can ensure a more stable and sustainable income, freeing them from the 'hamster wheel' of chasing brand deals. Jump into the Conversation: [02:32] Why financial literacy is a challenge for creators [07:46] Finding and fostering a relationship with the right co-founder [24:39] Different paths to finding an operational partner [29:23] The importance of back office finance for creators [43:41] Structuring a business with multiple product lines [51:24] Compensating employees with equity [01:01:13] Building membership programs [01:09:24] Cultivating talent for Creator COO roles [01:11:20] Finding the right operating partner Continue the conversation with these resources: Follow Eric Wei on LinkedIn

The key to making a multi-million dollar business out of a creator? Strategic hiring.  In this conversation, Alex Dwek, COO of Nas Company, dives into diversifying a creator's business to ensure growth without relying entirely on the personal brand of the creator.  He discusses the transition from relying solely on a creator's personality towards building a self-sustaining brand that resonates with the audience's values. He shares how he navigated this challenge at Nas Daily by moving from a focus on ad revenue to creating educational courses that embody the essence of the brand.  Alex also shares insights into the financial side of creator businesses. He discusses his experience raising $23 million, shares funding options for creator businesses, and explores compensation plans that attract top talent in a competitive market. Show Notes: Here are the key takeaways from our conversation with Alex: Realities of VC Funding in the Creator Economy:While venture capital can fuel explosive growth, creators and COOs need to understand the implications of taking VC money. Alex demystifies the process of raising $23 million, emphasizing the importance of good business fundamentals and profitability. He explains various funding avenues, such as bootstrapping, crowdfunding, and VC investment. He also advises careful consideration of the consequences each path may present on creative control and decision-making. The Secret to Finding the Right Creator COO:Alex shares strategic hiring practices and the importance of matching business needs with a candidate’s skills. He explains how avoiding immediate COO titles can benefit your company and the significance of finding individuals who are not just skilled but are a cultural fit. Creators and COOs will learn the subtle art of interviewing, the weight of social proof in attracting top talent, and how transparency in financials can influence hiring. Cultivate Transparency and Long-Term Strategic Vision:Transparency and strategic long-term planning are recurrent themes in Alex's experience. He shares how to build a sustainable creator business that's focused on long-term growth rather than immediate returns. He encourages creators and Creator COOs to transparently share financials, embrace equity plans or profit-sharing, and understand the operational work needed to build a brand that stands the test of time.  Jump into the Conversation: [01:08] How content creation is shifting control from institutions to individuals [08:30] Building a business that reaches beyond the creator’s personality [12:25] How Creator COOs can effectively enter a creator’s business [25:17] The biggest mistake creators make in hiring Creator COOs [33:51] Attracting Creator COOs in a competitive market [41:00] Compensation plans for creator businesses [51:06] Building a durable business with software products and services [01:01:33] Why VCs evaluate founder-market fit [01:11:58] Alternatives to VC funding for creator businesses Continue the conversation with these resources: Follow Alex Dwek on LinkedIn and X Read The Go Giver, a book about unexpected returns on generosity Check out Nathan Barry’s blog post about ConvertKit’s profit-sharing plan Read about Basecamp’s approach to compensation in this post

As power shifts from institutions to individuals, creators have a unique opportunity to build enterprise empires in their niches. To make this happen, creators often need the help of outside investors, including venture capital firms (VCs).  In this episode, Megan Lightcap, Principal at Slow Ventures, walks us through the thought process of VC investors, explaining the unique dynamics of funding creator businesses. She shares why VC investment firms are strategically investing in creator businesses. She also delves into the strategies, insights, and considerations that VCs have when evaluating and investing in the ever-evolving creator economy. Megan highlights the untapped possibilities for creators to identify and capitalize on white space opportunities. She shares how creators can leverage their loyal followings and insider knowledge to make substantial industry impacts with the help of VC investors. Show Notes: Here are the key takeaways from our conversation with Megan: Maximize Your Unique Industry Position:Megan spotlights the inherent advantages creators have in areas such as consumer product goods (CPGs). By having early retail distribution and avoiding the initial hurdles of brand awareness, creators can uniquely position themselves in the market. Megan emphasizes the significance of authentic audience engagement over merely securing endorsement deals. Creators have the unique ability to identify white space opportunities and pivot toward industries where they can leverage their embedded distribution and industry knowledge. Capitalize on Your Community: Megan discusses the power of creators to transform their loyal followings into thriving enterprises. By leveraging personal brands, creators have the unique opportunity to bypass traditional hurdles in pathways such as retail distribution. Megan shares how VC funding frees creators to strategically invest time and resources into their personal brand, enabling them to step back from day-to-day content creation without sacrificing their business's growth. Structure for Flexibility and Growth with the Top Co Model: Megan advocates for investing in top cos as a strategic way for creators to access funding while retaining flexibility. This approach, which involves creating a top holding company with various underlying projects, provides the benefit of separating the creative aspects from the business opportunities. Megan shares how creators and COOs interested in VC funding can position themselves for investment in a way that still allows for experimentation and growth. Jump into the Conversation: [05:12] Why equity can be a better fit for creator businesses than debt [12:07] When and why creators should raise capital [14:43] The role of Creator COOs in raising capital [16:44] Mitigating the risk of the creator lifecycle [28:44] Evaluating creators to invest in [30:17] The impact of cult-like followings [41:42] Helping creators navigate long-term planning [44:30] Underwriting creator businesses [49:14] Why VCs invest in creator top cos [55:24] Maintaining lifestyle business versus building a bigger enterprise Continue the conversation with these resources: Follow Megan Lightcap on LinkedIn and X

Are celebs missing out on the growth of the creator economy?  Direct-to-consumer (D2C) and owned media are the next great frontiers for A-list stars who want to maximize their media presence…and earnings.  The challenge they face? Finding the right team to make it happen. In this conversation, Andrew Graham, an agent with CAA's digital media team, explores the dynamic world of direct-to-consumer strategies and the rising influence of owned media. Drawing from experiences with celebrities like Zac Efron and Tim McGraw, we discuss the importance of building the right team to support new ventures.  Andrew also shares his knowledge on packaging and monetization of original intellectual property (IP) and projects. Forging strategic brand partnerships with global advertisers, and bridging the gap between traditional entertainment and modern creators. He also explains how talent is reshaping the roles of managers and agents and turning digital ecosystems into powerful agencies Here are the key takeaways from our conversation with Andrew: Build the Right Team:Andrew shares a critical piece of advice for creators and celebrities alike: you're not alone in this journey. So assemble a team with specialized knowledge. Andrew suggests you start with a manager who can help guide your growth. Then you can scale to partner with experts or bring that expertise in-house. This lets you focus on the good stuff: creating the content your audience wants. And let the experts handle the operations Leverage Your Personal Brand for Long-Term Success:To see success align your core business, like film, TV, or music, with your personal brand strategy. This episode highlights real examples of this, with celebrities like Tim McGraw, who’ve managed to build media brands around their personalities. Andrew also encourages creators to foster deep relationships with their audience, which has become increasingly important in a post-pandemic world. Embrace the Role of Talent Agencies in Your Career:Talent agencies are changing, moving towards equity participation and creating long-term, high-value content. He urges creators and celebrities to align with an agency that understands both their vision and the new standards and practices around tech and content creation. He emphasizes the need for a clear strategy when partnering with an agency to maximize all potential revenue streams.  Jump into the Conversation: [05:08] Transitioning A-list celebrities into social media influencers [11:11] Embracing the ‘talent as a publisher’ approach [15:09] Recent trends in management companies  [17:17] Navigating the spectrum of celebrity involvement in business ventures [20:59] Maximizing long-term value by building the right team [25:54] Case study in celebrity-owned media: Down Home, Tim McGraw’s media company [32:38] Embracing direct-to-consumer ventures [35:17] The future of talent agency and talent management  [38:21] Mitigating the risk of AI to talent and creators [41:26] Advice for choosing an agency partner    Continue the conversation with these resources: Follow Andrew Graham on LinkedIn and X