Up Arrow Podcast

Curtis Matsko is the Founder and CEO of Portland Leather Goods, a DTC high-quality leather goods company. He built the brand out of his garage, scaling it from zero to over $100 million in yearly revenue. As a serial entrepreneur and digital marketing expert, Curtis has worked in design production, marketing, and customer service.  In this episode… When scaling your business, it’s essential to recognize that what got you from zero to $10 million won’t get you from $10 to $100 million. Significant revenue jumps entail higher costs and larger operations, so relying on your previous successes will only hinder you. How can you break through the glass ceilings of growth? As a self-proclaimed e-commerce genius, Curtis Matsko launched his brand out of his garage and scaled it to $150 million. He maintains that steady growth begins with in-house production to create high-quality products that drive sales and foster customer loyalty. As your customer base grows, you can build products that generate customer lifetime value and acquire new customers. Another aspect of profitable growth involves building a team that can grow with your business. This requires hiring candidates whose personal and professional goals align with desired positions by conducting thorough interviews that emphasize key personality traits and experiences. In today’s episode of the Up Arrow Podcast, William Harris welcomes Curtis Matsko, the Founder and CEO of Portland Leather Goods, to talk about creating a foundation for profitable long-term growth. Curtis explains how to build a solid customer retention cycle, how he created Craigslist ads to acquire talent, and how overcoming alcohol addiction influenced his growth and decision-making mindset. 

Jimmy Slagle is the Co-founder of EVA, an AI creative strategist for e-commerce brands. He is also the Co-founder and CEO of generAI, which helps businesses implement AI-powered strategies. As an expert in creating and scaling ads for Fortune 500 companies, Jimmy began his career scaling Instagram accounts before founding a TikTok agency and working with major clients like Amazon and Lyft.  In this episode… Creators in e-commerce companies often select a single AI tool for their ads or content and are met with limited or recycled outputs. As AI becomes a trend that can hinder or accelerate business growth, how can you harness this technology to gain a competitive edge? According to AI developer Jimmy Slagle, AI tools must be trained to produce founder- and creator-led content that advances creativity. You can leverage various AI-driven tools to develop a cohesive output and strategy. For instance, Google AI Studio allows you to upload video files to create high-performing ads customized to your brand strategy by mimicking your creative process. This tool can also identify areas for improvement in each campaign. Additionally, Claude provides tips for creating viral social media content and measuring it against competitors. In today’s episode of the Up Arrow Podcast, William Harris chats with Jimmy Slagle, the Co-founder of EVA, about strategic methods for leveraging AI in e-commerce. Jimmy shares ethical and unethical uses of AI, how to create AI-powered UGC, and how he scaled and flipped Instagram accounts in high school.

Christian Limon is the former Chief Growth Officer at Wish, which was the top spending advertiser on Google and Facebook. He was also the Chief Growth Officer at Tubi and Gemini. Throughout his career, Christian has achieved five exits and $28 billion in IPO and M&A proceeds. He has launched 20 apps and led 33 more apps on growth and monetization.  In this episode…  Data-driven marketing and advertising has become a trend, with advertisers misunderstanding information and leveraging surface-level data to fit their narratives. How can companies implement data effectively to become top performers on high-traffic platforms? While algorithms on platforms like Meta and Google can help generate ideas, you shouldn’t use them to structure your entire campaign. For instance, you may notice your algorithms targeting one audience group while your sales rates suggest higher engagement levels among another audience group. Having led one of the top advertisers on Meta and Google, Christian Limon suggests identifying the micro and macro factors impacting your campaign, like the economy, consumer preferences, and platform popularity, to match demand. In the latest episode of the Up Arrow Podcast, William Harris chats with Christian Limon about advertising on Meta and Google beyond leveraging data-driven insights. Christian shares his experience scaling multiple brands, the latest investment and Bitcoin trends, and common advertising misconceptions.

Clayton Christopher is the Founder of Astō Consumer Partners, a CPG-focused investment firm. He is also the former CEO and Founder of Sweet Leaf Tea, an organic bottled tea company he started with only $10,000 before selling it to Nestlé. Clayton co-founded and was the Chairman for Deep Eddy Vodka, which became one of the fastest-growing spirits brands under his leadership. As a serial entrepreneur in the CPG space, he co-founded Waterloo Sparkling Water and Rhythm Super Foods, among other brands. Clayton is also a board member and investor in various CPG brands and was awarded the Ernst & Young Entrepreneur of the Year for Central Texas.  In this episode… As a digitally native brand, getting your products into consumers’ hands before launching them isn’t always feasible. Expanding into retail channels allows you to reach a wider audience and promote your products. What should you know before transitioning into retail, and how can you optimize your presence in the market? Digitally native brands that transition to retail often lose some DTC customers to competitors. Multipreneur Clayton Christopher suggests building a core customer base by offering samples at music festivals or creating memorable in-store experiences to showcase product quality and drive loyalty. He also recommends refining packaging to communicate key product attributes effectively and ensuring organizational focus on strategic priorities to support retail success. These approaches strengthen retail performance, enhance brand visibility, and create lasting consumer relationships. In this week’s episode of the Up Arrow Podcast, Clayton Christopher, the Founder of Astō Consumer Partners, joins William Harris to talk about launching CPG brands into retail channels. Clayton explains the importance of launching in a niche market first, his leadership framework for brand growth, and how he built, scaled, and sold his brands.

Pam Didner is a B2B marketing consultant, fractional CMO, speaker, and author. With 20 years of experience in B2B marketing, she helps companies bridge the gap between technology and marketing to build seamless customer experiences and boost sales. Pam is also the author of The Modern AI Marketer book series, which includes The Modern AI Marketer in The GPT Era, The Modern AI Marketing: Guide to Gen AI Prompts, Effective Sales Enablement, and Global Content Marketing.  In this episode…  AI is still just an algorithm and isn’t at the human intelligence level, yet many marketers provide generic inputs yielding subpar results. AI doesn’t understand your brand story or target audience, so you must provide specific information for valuable results. How can you create winning AI prompts to elevate your brand? Generative AI expert and B2B marketer Pam Didner recommends customizing AI prompts to your brand goals. This includes creating detailed, context-rich prompts to guide AI to meaningful and actionable outputs. For instance, a strong prompt should include specifics such as target audience details, product descriptions, competitor insights, and the generated content’s intended outcome. To maximize results, Pam suggests training AI systems on proprietary data sets, allowing you to develop custom bots that automate repetitive tasks, streamline workflows, and create consistent outputs.  In the latest episode of the Up Arrow Podcast, William Harris invites B2B marketing consultant Pam Didner to speak about engineering custom AI prompts for your business. Pam shares her recommended AI tools for image and content creation, how to overcome growth barriers, and the importance of treating your customers with dignity.

Jeremiah Prummer is the CEO of KnoCommerce, which specializes in customer survey integrations for e-commerce brands. With nearly 15 years of entrepreneurial experience, he started in e-commerce building extensions for WooCommerce. Jeremiah specializes in conversion rate optimization and zero-party data. In this episode…  When it comes to customer service, many brands don’t elicit sufficient feedback to improve the experience. Asking detailed questions in comprehensive surveys offers rich insights and data. How can you leverage this information to drive conversions? Rather than relying solely on customer reviews to gather information about their experiences and service levels, data and attribution expert Jeremiah Prummer suggests integrating surveys at various points during the customer journey. For instance, you can provide post-purchase and abandoned cart surveys with multiple open-ended and specific questions, including why they made the purchase, detailed information about their experiences, and where they heard about the brand. This offers actionable data you can harness to innovate your products, attribute purchases to various metrics, and retain customers. In this week’s episode of the Up Arrow Podcast, William Harris sits down with Jeremiah Prummer, the CEO of KnoCommerce, to discuss optimizing customer surveys to scale. Jeremiah talks about gathering customer data beyond basic demographic information, how to attribute customer data to various business metrics, and how innovation solves universal problems.

Join Andy Crestodina, co-founder and CMO of Orbit Media Studios, as he revolutionizes the use of AI in marketing. He emphasizes identifying deficiencies instead of simply striving for efficiencies, warning against generic content that dilutes your brand. Discover how AI can analyze and enhance web content, improve SEO, and create ideal customer personas. Andy also shares insights on optimizing e-commerce landing pages and discusses consumer readiness for AI in various sectors, ensuring your marketing is both innovative and effective.

Matt Van Swol is the Head of Subscription Growth at Wyze, a smart home technology company. He has held multiple roles at the company, including Creative Marketing Manager and Senior Growth Manager. Before Wyze, Matt was a Nuclear Scientist for the US Department of Energy, where he worked on classified and unclassified projects at the Savannah River National Laboratory. He was also a photographer and marketer for big-name companies, including Apple, United Airlines, and Hyatt Hotels.  In this episode… Subscription-based businesses rely on consistent customer engagement and feedback to scale, yet many companies over-complicate their subscription models by integrating the latest market trends rather than what the customers want. How can you create a consistent customer feedback flywheel to build your subscriptions and generate multiple figures in revenue? Customer-focused and versatile professional Matt Van Swol has generated nearly nine figures in revenue for a home technology brand by listening to the customers. He initiates open-ended post-purchase and cancellation surveys to generate honest feedback that influences future subscription models. However, Matt emphasizes evaluating feedback thoroughly before integrating it into subscription models to ensure alignment with business goals and customer engagement levels. Consistent and transparent communication through email or SMS is crucial in building high-performing subscription models. In the latest episode of the Up Arrow Podcast, William Harris welcomes Matt Van Swol, the Head of Subscription Growth at Wyze, to talk about integrating customer feedback into subscriptions. Matt shares how to leverage AI intentionally, how to craft offerings tailored to the customer, and the impact of Hurricane Helene on local businesses.

Luke Schneider is the Founder and CEO of Fire Dept. Coffee, a certified veteran-owned coffee company. Fire Dept. Coffee gives back to and supports injured firefighters and has been named to the Inc. 5000 list three years in a row. Luke is also a retired firefighter, paramedic, and US Navy veteran. In 2023, he received the Leadership award for Citizenship from the Specialty Food Association.  In this episode…  In a business environment dominated by duplicate products, brands must employ creative measures to stand out and capture consumers’ attention. This requires more than having a widespread presence on popular social media apps. How did a community-focused coffee brand gain recognition in thousands of Walmart locations? Former firefighter and US Navy veteran Luke Schneider credits his coffee company’s growth to a robust community presence and a resonant mission. He emphasizes building a local community to convey your mission and cultivate a brand identity. For a broader reach, you can communicate your message on various social media platforms by targeting audiences who align with your mission to differentiate your products in the market. Luke maintains that a motivated team and influential culture can promote your community efforts and amplify your mission.  In today’s episode of the Up Arrow Podcast, William Harris chats with Luke Schneider, the Founder and CEO of Fire Dept. Coffee (FDC), about building a robust community and team to scale. Luke discusses social selling, FDC’s subscription offers, and how the company received its first publicity and navigated a trademark lawsuit.

Andrew Gerrie is the Founder of Mend, an independent public relations and communications agency for outdoor and active lifestyle brands. With nearly a decade of experience in PR and communications, he has built media strategies for brands, including Tecovas, Sims, Filson, and Costa Del Mar, helping them craft and amplify their unique brand stories. Before founding Mend, Andrew held several roles at Backbone Media, including Senior PR Account Manager and PR Account Coordinator.  In this episode…  Modern PR methods have become inauthentic, making it challenging to maintain genuine brand narratives. As the influencer culture evolves and the digital landscape becomes oversaturated with sponsored content and poor storytelling, how can brands cut through the noise to tell their authentic stories? According to media strategist Andrew Gerrie, building relationships with writers and journalists is the first step to improving storytelling quality. This may involve offering these media professionals free products as gifts, allowing them to understand your mission and product initiatives to craft authentic messages. When expanding locations or launching new products, you can partner with local media outlets to generate a regional community presence and stand out in the market. If you want to reach a broader audience, consider integrating current trends into your PR campaigns, ensuring they align with your brand voice and story. In this episode of the Up Arrow Podcast, William Harris sits down with Andrew Gerrie, the Founder of Mend, to discuss PR strategies for e-commerce brands. Andrew shares why products are the secret to effective PR campaigns, how to measure results from your efforts, and how to appear in popular holiday gift guides.