Mike Maples is the co-founding partner at Floodgate, a venture capital firm that focuses on early stage investments in technology companies. He has been featured on the Forbes Midas List eight times in the past decade, recognized as a “Rising Star” by FORTUNE, and profiled by Harvard Business School for his enduring contributions to entrepreneurship. As a founder and operating executive, Mike played pivotal roles in two successful IPOs: Tivoli Systems (later acquired by IBM) and Motive (acquired by Alcatel-Lucent). 

Mike’s career as a seed investor has solidified his legendary status in Silicon Valley. Some of his notable investments include Twitter, Twitch.tv, Clover Health, Okta, Outreach, Chegg, Demandforce, and Applied Intuition. Together with Stanford Professor Peter Ziebelman, Mike developed insights on identifying "Pattern Breaking" concepts, referred to as "Inflections." These ideas form the foundation of his book, Pattern Breakers, which explores over 15 years of investment experience to reveal the sources of breakthrough potential in startups. The book is a National Bestseller and ranks as the #1 Venture Capital book on Amazon.

On today’s show, Alan and Mike dive into Mike’s latest book, Pattern Breakers, exploring what pattern breakers are, their key components, and how they drive transformational change. They examine the concept of inflection points, pivotal moments that define the trajectory of a startup. Mike explains the importance of being radically different and the necessity of building a movement around your business and products to stand out in competitive markets. They also explore what truly makes a company radically different and how these elements come together to fuel extraordinary success.

In this episode, you'll learn:

• Why being radically different is essential for startups and how to achieve it
• Strategies to identify and connect with your ideal customer base early 
• Key startup principles that even large companies can adopt, plus actionable tips for collaborating with startups

Key Highlights:

• [02:17] Being a professional calligrapher  
• [03:32] Career path to Floodgate
• [05:50] Why is now the right time for the book, Pattern Breakers
• [08:53] Why startups need to be radically different
• [14:00] Is getting competition good or bad
• [15:58] How to find the customer base early on
• [18:59] How the principles of a startup can apply to large companies
• [22:28] Tips for large companies working with startups
• [23:46] Risk profiles and mindsets 
• [26:16] Inflections 
• [30:05] Different categories of growth
• [32:05] Inflections, pattern breakers, creating movements relating to marking
• [34:04] Does radically different only matter if its a commercial success
• [37:50] An experience from your past that defines you
• [41:35] Advice to your younger self- personal monopoly 
• [43:50] A topic that you and other marketers need to learn more about - AI 
• [50:12] Trends or subcultures others should follow
• [50:51] Largest opportunity or threat to marketers today

Looking for more?

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Brian Goldfarb is the Senior Vice President and Chief Marketing Officer at SolarWinds. After earning his A.B. in Computer Science and Economics from Duke University, Brian initially explored a career on Wall Street but soon transitioned to product management at Microsoft, marking the start of his two-decade journey in the tech industry. At Google, Brian played a key role in launching the Cloud Platform. He later led platform marketing at Salesforce, and before joining SolarWinds, he served as CMO at both Splunk and Tenable. Now, after nearly a year with SolarWinds, Brian oversees the company’s global marketing strategy, covering its industry-leading observability, database, and service management solutions.

SolarWinds is a leading IT management software provider that helps businesses monitor and manage their IT infrastructure, applications, and networks. Known for its user-friendly and scalable solutions, SolarWinds serves a broad range of industries, focusing on identifying and resolving IT challenges. SolarWinds continues to deliver solutions that empower IT professionals to maintain reliable and secure environments.

In today’s show, Alan and Brian dive into cybersecurity, discussing SolarWinds and the solutions they offer. They examine the major cybersecurity incident that impacted both the company and the industry and how SolarWinds successfully recovered from it. Additionally, they explore what marketing looks like at SolarWinds, how the role of CMO has evolved, and what we should consider about the future of this role.

In this episode, you'll learn:

• Insights for successfully recovering from a massive cyberattack
• Tips for creating a strong marketing structure
• The profile of the modern CMO and how it has evolved

Key Highlights:

• [01:15] Brush with fame on a game show
• [03:08] Career path to CMO at SolarWinds
• [05:29] Story behind Kubernetes 
• [07:23] Scope of SolarWinds
• [10:39] Recovering from a massive cyberattack
• [14:25] How marketing is structured at SolarWinds
• [15:52] What CMO role should be focused on
• [17:56] How the CMO role interacts with the rest of the team 
• [21:20] “Lack of novelty is not a bad thing”
• [27:30] An experience from your past that defines you
• [30:24] Advice to your younger self
• [31:36] A topic that you and other marketers need to learn more about
• [33:11] Trends or subcultures others should follow
• [36:30] OOH Advertising’s impact internally 
• [37:30] Largest opportunity or threat to marketers today

Looking for more?

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Anna Bager is the President and CEO of the Out of Home Advertising Association of America (OAAA). Before joining OAAA, Anna spent 15 years in the telecom industry, beginning with the global research firm IDC. She then moved to the client side at Ericsson Multimedia, where she led mobile advertising initiatives in Sweden as the Head of Research and Business Intelligence. After relocating to the U.S., she served as Executive Vice President of Industry Initiatives at the Interactive Advertising Bureau (IAB). Five years ago, Anna became the CEO of OAAA, and her industry contributions have earned her numerous accolades. She has been recognized as one of the "Most Powerful Women in Mobile Advertising" by Business Insider and as one of the "Top Women in Media" by Folio Magazine and Cynopsis Media. Most recently, Anna was honored as one of Campaign’s "Most Inspiring Women of 2024."

Out-of-Home Advertising (OOH) is a form of advertising found outside of a consumer’s home. Traditionally, this includes everything from billboards to bus shelters, benches, etc. The Out-of-Home Advertising Association of America (OAAA) is the leading trade association representing the out-of-home (OOH) advertising industry. OAAA's membership includes over 850 media companies, advertisers, agencies, ad tech providers, and suppliers. Since its founding in 1891, OAAA has advocated for the responsible growth of OOH advertising.

On today’s show, Alan and Anna discuss her unique perspective on the advertising industry and the changes she anticipates. They explore the role of out-of-home (OOH) advertising within the broader marketing mix, recent innovations in the OOH industry, and how the upcoming election is influencing — and being influenced by — OOH. Additionally, they examine how OOH fits into the landscape with the rise of retail media networks.

In this episode, you'll learn:

• How the election is impacting Out-of-Home advertising—and how OOH is impacting the election
• Emerging shifts in advertising and where OOH plays a pivotal role
• How Out-of-Home integrates into the growing landscape of retail media

Key Highlights:

• [01:18] Experience as a backgammon master
• [02:34] Career path to OAAA
• [05:02] How do you see advertising today changing
• [08:17] How does Out of Home fit in the broader marketing mix
• [10:08] What is new in the Out of Home industry
• [13:55] How Out of Home and the election impact each other 
• [18:00] What is the role of Out of Home in retail media 
• [20:40] An experience from your past that defines you
• [21:42] Advice to your younger self
• [22:15] A topic that you and other marketers need to learn more about
• [24:00] Trends or subcultures others should follow
• [24:45] Largest opportunity or threat to marketers today

Looking for more?

Visit our website for the full show notes, links to resources mentioned in this episode, and ways to connect with the guest!

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Andrew Bennett is the CMO at Conga, a revenue lifecycle management company. After graduating from Dartmouth College with a bachelor's degree in computer science, he began his career in tech at Onyx Software, where he led professional services for nine years. He later pursued his entrepreneurial aspirations by running a successful fly-fishing lodge business for almost a decade. Returning to the tech sector, Andrew joined Smartsheet, where he built the company’s digital marketing and demand generation capabilities, led commercial sales, and ultimately served as CMO for his last three years, during which Smartsheet achieved over $1 billion in ARR. Six months ago, he joined Conga, where he now focuses on enhancing the company’s global brand and driving demand for its offerings.

Conga is a revenue lifecycle management company offering solutions across three main pillars: contract lifecycle management, document automation, and configure, price, and quote (CPQ). What sets Conga apart is its unified platform, where all these products seamlessly integrate to support customers’ needs.

In today’s show, Alan and Andrew discuss Andrew’s role at Conga and his efforts to drive alignment between sales and marketing. They delve into MarTech stacks, exploring how to prioritize and optimize these investments, along with strategies for measuring the real financial impact of marketing efforts.

In this episode, you'll learn:

• Strategies to align marketing and sales
• How to prioritize and rationalize MarTech stacks
• Steps to meaningfully measure the impact of your marketing

Key Highlights:

• [01:27] Merging fly-fishing and MarTech
• [04:50] Career path to CMO of Conga
• [07:52] What is Conga
• [10:15] How to bring marketing and sales together and get them aligned
• [15:40] Rationalizing and maximizing MarTech stacks
• [18:40] Approaching impact measurement
• [23:30] Net dollar retention rate
• [24:34] Leveraging partnerships for brand and results
• [29:50] An experience from your past that defines you
• [31:02] Advice to your younger self
• [33:22] A topic that you and other marketers need to learn more about
• [35:02] Trends or subcultures others should follow
• [37:34] Largest opportunity or threat to marketers today

Looking for more?

Visit our website for the full show notes, links to resources mentioned in this episode, and ways to connect with the guest!

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Brian Cooley is the Chief Marketing Officer at PlayVS, a leading scholastic esports platform in North America, where he brings over 25 years of experience in marketing. His marketing career began in the automotive industry with Land Rover North America, where he spent three years focusing on customer relationship marketing and retail operations. Brian then transitioned to the tech industry, spending six years with IBM. He continued his tech-focused trajectory at Blackboard, where he served as Senior Director of Global Marketing Services before advancing to Vice President of Global Demand Generation. Brian spent the next nine years as CMO at EverFi, deepening his role in edtech by leading the company’s marketing strategy. Now, in his first year as CMO of PlayVS, he leverages his rich background in edtech and marketing to drive growth and expand the platform’s reach in the competitive scholastic esports market.

PlayVS was founded in 2018 and is now a leading esports platform in North America, partnering with the National Federation of State High School Associations (NFHS) to provide and host organized competitive gaming in high schools across all 50 U.S. states and Canada. As of November 2023, PlayVS expanded access by removing enrollment fees for its state and regional leagues, making participation free for high schools. This initiative has likely increased the number of participating schools, which was around 4,000 as of late 2023.

In today’s show, Alan and Brian dive into the booming market for collegiate and scholastic esports, exploring how partnerships with professional sports leagues are creating new opportunities for access and growth. They also discuss PlayVS’s collaboration with the Special Olympics to increase accessibility for students and why esports and gaming are essential areas for marketers to watch closely.

In this episode, you'll learn:

• How marketing to the new generations changes the game
• Why marketers should pay attention to esports and gaming
• What to consider when partnering with an influencer

Key Highlights:

• [01:37] How growing up in many different countries has influenced you
• [03:03] The most interesting meal from your travels
• [04:52] Career path to PlayVS
• [08:33] What is PlayVS
• [10:35] How PlayVS got started
• [15:17] The esports that PlayVS focuses on
• [17:42] Partnerships with pro sports
• [20:35] Partnership with the Special Olympics
• [22:17] Why marketers should care about esports and gaming
• [26:02] Experience from your past that defines you
• [28:10] Advice to your younger self
• [30:12] A topic that you and other marketers need to learn more about
• [32:29] Trends or subcultures others should follow
• [34:45] Largest opportunity or threat to marketers today

Looking for more?

Visit our website for the full show notes, links to resources mentioned in this episode, and ways to connect with the guest!

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Joe Gaither is the CMO of Feetures, a high-performance sock brand. He joined Feetures in 2009 as a tech rep supporting sales, traveling to 49 states, meeting with thousands of retailers to strengthen Feetures' B2B partnerships and establish it as their preferred sock brand. Joe transitioned into a leadership role, managing the sales force in the Western United States. He later shifted his focus to marketing, where he helped build and grow Feetures' marketing department and expanded its Direct-to-Consumer sales channel. Today, Joe oversees marketing, ecommerce, and customer service, three key components of the customer experience. Under his leadership, direct-to-consumer sales have become the fastest-growing segment of the business.

Feetures is a brand known for producing high-performance socks designed for both athletic and everyday wear. The brand emphasizes comfort, durability, and foot health, using targeted compression, anatomical design, and moisture-wicking fabrics to provide superior support. Their seamless construction makes them a favorite among runners, hikers, and other active individuals. Feetures holds the title of America’s #1 running sock brand by market share in the run specialty industry.

In today’s show, Alan and Joe discuss the evolution of Feetures, which began as a family business launched by Joe’s father. They explore the brand’s future, including the upcoming launch of their first non-sock product in the U.S., marking their expansion beyond their core category. They also dive into the current state of the running industry, strategies for standing out in a crowded market, and the challenges of navigating the landscape as an omni-channel brand.

In this episode, you'll learn: 

• What it takes to stand out in a crowded market
• The mindset behind navigating as a successful omni-channel brand
• Key considerations when deciding to launch into a new category

Key Highlights: 

• [01:45] Sibling CMO’s, is marketing in the DNA 
• [03:09] Path to CMO at Feetures
• [07:33] What is the scope of Feetures
• [10:05] Family business and a shift of generations
• [12:08] Current state of the running industry today
• [15:51] Differentiating in cluttered category
• [18:45] Expansion with new product 
• [22:03] Being an omni-channel brand 
• [26:17] Experience of your past that defines you
• [28:24] Advice to younger self
• [29:17] A topic that you and other marketers need to learn more about
• [31:11] Trends or subcultures others should follow
• [32:30] Largest opportunity or threat to marketers today

Looking for more?

Visit our website for the full show notes, links to resources mentioned in this episode, and ways to connect with the guest!

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Sue Hermann is the Senior Vice President and Chief Marketing Officer at BOK Financial. She holds a bachelor's degree in journalism from the University of Missouri and began her career in public relations. As Director of Corporate Communications and Content, she led a team responsible for internal and executive communications, public relations, and content development. Later, she became the Senior Vice President and Director of Communications at CoBiz Financial Inc. When BOK Financial acquired CoBiz Financial in 2018, Sue joined BOK Financial, where she had served as Director of Communications since 2000 and CMO since 2022.

BOK Financial Corporation, headquartered in Tulsa, OK, is a top 25 U.S. bank with $50 billion in assets and a wealth division managing over $107 billion in assets under management and administration. While rooted in the Midwest and Southwest, BOK Financial serves clients nationwide. The corporation operates under various names, including Bank of Oklahoma and Bank of Texas, with a diverse range of services. In addition to commercial and consumer banking, BOK Financial offers brokerage, trading, investment services, mortgage origination and servicing, as well as one of the nation's top 10 electronic funds transfer networks.

On today’s show, Alan and Sue discuss her journey to becoming CMO at BOK Financial and the current state of marketing and banking today. They also delve into gender diversity in finance, balancing a career with motherhood/parenthood, and what leaders need to recognize about their teams to foster the right environments and cultures.

In this episode, you'll learn: 

• The importance of gender diversity in finance
• Marketing trends impacting the banking industry
• Insights and challenges from balancing motherhood and career

Key Highlights: 

• [01:15] Wanting to be a coroner 
• [02:39] Career path to CMO at BOK Financial 
• [05:02] What is BOK Financial 
• [07:00] The current state of marketing today
• [08:12] The importance of relationships
• [09:36] Gender diversity 
• [14:12] Approach on blending parenthood and career
• [20:20] What insight leaders need to take from parenthood
• [24:34] Experience of your past that defines you
• [25:40] Advice to younger self
• [25:56] A topic that you and other marketers need to learn more about, AI
• [27:45] Trends or subcultures others should follow, Gen Z
• [29:15] Largest opportunity or threat to marketers today, noise 

Looking for more?

Visit our website for the full show notes, links to resources mentioned in this episode, and ways to connect with the guest!

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Shiri Hellmann is the VP of Global Brand Communications at Fiverr, with extensive experience in brand building, e-commerce, and consumer goods. Her diverse career began on the agency side before transitioning to the client side, where she led marketing communications for Bezeq International, Israel's largest telecommunications company, handling both B2B and B2C services. She later served as Head of Global Marketing Communication at SodaStream, overseeing campaigns in over 42 countries. Shiri then became VP of Marketing for SodaStream in the US, spearheading the brand's first Super Bowl ad. After returning to Israel, she freelanced with startups, focusing on brand strategy, research, and campaign execution. Shiri began using Fiverr in her freelance work and has since joined the Fiverr team as VP of Global Brand Communications. 

Fiverr is an online marketplace created to revolutionize the way the world collaborates by democratizing access to talent. Today, it is the largest marketplace of its kind, connecting freelancers and businesses in over 160 countries and offering more than 700 categories to choose from. 

On today’s show, Alan and Shiri discuss her journey to Fiverr and the increasing shift toward freelancing. They highlight the projection that by 2027, half of the U.S. workforce will be freelancing in some capacity and explore how Fiverr is positioning itself to capitalize on this trend. The conversation then turns to the impact of return-to-office mandates and the growing influence of AI in the freelance industry.  They also dive into the recent campaign featuring Martha Stewart as a participant in the Fiverr freelance community.

In this episode, you'll learn: 

• The importance of understanding local culture when driving global marketing success
• The impacts of return-to-office mandates
• How AI is affecting the freelance community

Key Highlights: 

• [01:40] Experience of being a birthday clown
• [03:22] Career path
• [09:07] What is Fiverr
• [10:30] How is Fiverr facilitating the freelance movement
• [12:35] Impact of return-to-office mandates
• [15:01] Impact of AI on freelance community 
• [19:28] Latest brand campaign with Martha Stewart
• [21:55] What makes great marketing
• [22:53] Experience of your past that defines you
• [24:37] Advice to younger self
• [25:09] A topic that you and other marketers need to learn more about
• [27:25] Trends or subcultures others should follow
• [30:25] Largest opportunity or threat to marketers today

Looking for more?

Visit our website for the full show notes, links to resources mentioned in this episode, and ways to connect with the guest!

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Christopher "Chris" Carl became the first U.S. Head of Marketing at AliExpress in 2023. Under his leadership, order volume increased by 60%, the brand's share of voice grew by 75%, headcount expanded by 400%, social media following surged by 500%, and brand awareness doubled. Chris’s impressive marketing career began as an intern at Calvin Klein. He then moved to BBDO in Germany, where he worked on pricing strategies, market expansions, and e-commerce development for European brands. Following this, he launched the U.S. office for Pulse Advertising, focusing on influencer marketing, and served as COO and President. He also founded his own men’s grooming brand before taking on his current role at AliExpress, where he continues to make a significant impact.

AliExpress is a global online retail platform owned by the Alibaba Group, headquartered in China. Launched in 2010, it connects buyers with a wide range of sellers, primarily manufacturers and wholesalers from China, offering products at competitive prices. AliExpress focus is on facilitating international trade by allowing businesses and individuals to sell a wide range of products to consumers around the world at an affordable cost.

On today's show, Alan and Chris discuss what AliExpress is and how it fits within the Alibaba Group. They explore advertising campaigns and partnerships, including the recent collaboration with UEFA and the latest campaign featuring David Beckham. Their conversation also touches on consumer behavior, the future of e-commerce, and how AliExpress plans to capitalize on emerging trends.

In this episode, you'll learn: 

• Strategies to enhance the online shopping experience while driving affordability
• Insights into consumer behavior and its implications for market positioning
• Innovative approaches to leverage emerging trends for competitive advantage

Key Highlights: 

• [01:35] Story of being brushed with fame in New York
• [03:13] Career path
• [07:20] Insights you gained from prior career experiences 
• [11:42] AliExpress’ aspirations in the U.S.
• [14:00] State of U.S. consumers today
• [16:30] Where AliExpress is focusing its energy
• [19:23] Campaign with David Beckham 
• [22:33] What’s next for AliExpress
• [24:55] Experience of your past that defines you
• [26:18] Advice to younger self
• [27:11] A topic that you and other marketers need to learn more about
• [28:13] Trends or subcultures others should follow
• [29:37] Largest opportunity or threat to marketers today

Looking for more?

Visit our website for the full show notes, links to resources mentioned in this episode, and ways to connect with the guest!

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Dave Edelman is a sought-after advisor on digital transformation and marketing, a professor, and an author. He teaches marketing at Harvard Business School and advises top executives on AI and personalization. Dave began his career as a young consultant at the Boston Consulting Group, where he coined the term “Segment-of-One Marketing.” Dave also guided Aetna (now part of CVS Health) as CMO through its transformation into a digitally oriented, customer-centric brand. Recognized multiple times by Forbes as one of the “Most Influential CMOs in the World” and by AdWeek as one of the “Top 20 Marketing and Technology Executives,” Dave has attracted over 1.1 million followers to his LinkedIn blog. His upcoming book, Personalized: Customer Strategy in the Age of AI, will be published by Harvard Business Press in October.

On today's show, Alan and Dave discuss Dave’s upcoming book and the importance of personalization for companies. They delve into the '5 Promises of Personalization,' exploring how effective personalization can transform a company's brand and value proposition over time. They also examine the key conditions required for successful personalization marketing, and how the personalization index can be used to assess and enhance a company's personalization practices. Additionally, they discuss how personalization can unlock the growth potential of AI.

In this episode, you'll learn: 

• The 5 Promises of Personalization and how they can add value to your company
• How AI can enhance personalized marketing
• Tips around building trust, a key component to personalization

Key Highlights: 

• [01:40] Dave’s passion as a jazz player & how it parallels business
• [03:35] How Dave got into personalization
• [07:13] Why this book and why now? 
• [09:03] Conditions needed for personalization 
• [13:33] The 5 promises of personalization 
• [18:40] Digging deeper into “Reach Me” 
• [23:10] How trust factors in 
• [25:33] How do you get better at “Delight Me”
• [28:44] Evolving your value proposition
• [32:00] Experience of your past that defines you
• [34:05] Advice to younger self
• [35:12] A topic that you and other marketers need to learn more about
• [36:27] Trends or subcultures others should follow
• [38:18] Largest opportunity or threat to marketers today

Looking for more?

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440: Entering the Consumer Market while Driving Sustainability with Elyse Winer CMO & GM of Consumer at GenPhoenix

Elyse Winer, CMO and GM of Consumer at GenPhoenix, began her career at Merrill Lynch before transitioning to healthcare consulting at Vynamic, where she gained branding and sales experience. She then moved into startups, leading marketing for Boston-based companies and collaborating with Reebok at MC10. Before joining GenPhoenix full-time, Elyse became a partner at Material Impact, a venture capital fund, where she served as interim CMO for GenPhoenix, overseeing a rebrand and their expansion into the consumer market. Her success in both startups and large companies has earned her numerous accolades, including Forbes' "30 Under 30" in Marketing & Advertising.

GenPhoenix, founded in 2007 for the aviation industry, is a market leader in the mass transportation seating category, with over 250 airlines using their material. Their technology breaks down waste leather to the fiber level and uses recycled water to rebuild the fibers, creating a product even stronger than before. This recycled leather has an 86% lower carbon footprint compared to traditional leather. GenPhoenix has since expanded into the leather goods and footwear industries, collaborating with brands like Coach and Dr. Martens. To date, they have diverted more than 10,000 tons of waste from landfills.

On today's show, Alan and Elyse discuss the sustainability of the fashion industry and its future direction. They explore how GenPhoenix is adapting, shifting from a predominantly B2B model to expanding into the consumer market. They also highlight partnerships with brands like Coachtopia and Dr. Martens, among others, and discuss strategies for promoting and protecting your brand in collaborations. Additionally, they discuss what early-stage companies and scale-ups, like GenPhoenix, should prioritize when allocating their marketing budgets.

In this episode, you'll learn: 

• Strategies when expanding into the consumer market
• How to protect and promote your brand in a collaboration
• What to prioritize when allocating marketing budgets, on a budget

Key Highlights: 

• [01:37] What Snoop Dogg is like 
• [04:36] Career path to GenPhoenix
• [11:00] What is GenPhoenix 
• [14:25] What combined role of CMO and GM of Consumer looks like
• [18:05] Sustainability in the fashion industry
• [23:45] Expanding into the consumer market
• [27:49] How to protect your brand in a collaboration
• [35:22] How being budget constrained can drive creativity
• [40:47] Experience of your past that defines you
• [43:40] Advice to younger self
• [45:19] A topic that you and other marketers need to learn more about
• [47:35] Trends or subcultures others should follow
• [50:00] Largest opportunity or threat to marketers today

Looking for more?

Visit our website for the full show notes, links to resources mentioned in this episode, and ways to connect with the guest!

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