Up Arrow Podcast

Harley Finkelstein, President of Shopify and co-founder of Firebelly Tea, dives into the transformative landscape of eCommerce. He emphasizes that consumers now dictate shopping experiences, shifting power from retailers. The conversation explores how augmented reality is revolutionizing product visualization, making online shopping more engaging. Harley also reflects on the harmony of digital and physical retail and the necessity for brands to adapt to community-driven values. His journey underscores the significance of creativity and resilience in entrepreneurship.

Marianne Zakhour is the Co-founder of OrderBot, an enterprise order, inventory, and product management software. She has led the company to double its yearly sales in seven years. With over 25 years of experience in B2B, B2C, and e-commerce system and process efficiencies, Marianne develops solutions to complex customer problems and builds teams to increase productivity and growth. In this episode… With the demand for online shopping accelerating, businesses must fulfill multiple orders under tight time frames. Yet many companies don’t have a reliable order management system, leading to frustrated customers and lost revenue. How can you codify your orders for customer retention and satisfaction? After becoming dissatisfied with fulfillment expectations and inventory discrepancies while consulting for a bakery, Marianne Zakhour recognized the value of a strategic order management system. However, she discovered that most businesses aren’t aware of the flaws in their systems and advises collaborating with internal management and external 3PL partners to identify and resolve issues. You can increase each order’s reliability by establishing and adhering to a fulfillment timeline, measuring customer order times, and obtaining visibility into your process. In today’s Up Arrow Podcast episode, William Harris sits down with Marianne Zakhour, the Co-founder of OrderBot, to discuss developing reliable order management systems. Marianne shares how she increases companies’ order management accuracy from 80-99.98%, the consequences of poor order management, and how to collaborate with 3PL businesses.

John Wong is the former Co-president of Jack Rogers, an American footwear and accessory brand. With over 20 years of experience at leading retail organizations, he has experience in multi-channel distribution, international and domestic sales, merchandising and planning, and e-commerce. John has worked with notable brands, including DFS Group, Coach, Marc Jacobs, and Tory Burch. In this episode… eCommerce comprises approximately 15% of total retail sales. Yet brands expend their marketing dollars and efforts exclusively on DTC channels, limiting brand awareness and reach. Alternatively, wholesale models allow you to acquire more customers and maximize lifetime value. What are the long-term benefits of wholesaling, and how can you capitalize on this sales method? With a wholesale model, brands provide the product, and third-party retailers manage checkout and distribution. While this restricts control over the customer experience, wholesale expert and brand builder John Wong says partnering with leading retailers like Macy’s and Nordstrom helps build your brand with an established consumer base. Additionally, DTC models require utilizing third-party logistics companies that charge a fee per shipment. Conversely, wholesale retailers ship bulk items to customers, leading to higher returns and profit margins. When partnering with retailers in a wholesale agreement, obtaining shelf space for your product can be difficult, so John recommends acquiring space in retailers’ digital marketplaces. In today’s episode of the Up Arrow Podcast, tune in as William Harris invites John Wong, the Former Co-president of Jack Rogers, to speak about leveraging wholesale models. John explains department-level P&L statements, the impact of virtual reality on the shopping experience, and why you should integrate wholesale and DTC marketing budgets.

Neal Schaffer is the Founder and President of PDCA Social, a digital marketing consultancy and social media agency. As a fractional CMO, he helps innovative businesses digitally transform their sales and marketing. Neal is a social media keynote speaker, having spoken about digital media on four continents in a dozen countries. He has written three books on social media, including Maximize Your Social and The Age of Influence, which educates the market on influencer marketing. In this episode… With brands leveraging social media marketing to acquire lifelong advocates, content creation must be enjoyable and entertaining. Rather than promoting products on various platforms, connect with your consumers by driving engagement. How can you market on social media to build a trustworthy brand? As a passionate digital marketer, Neal Schaffer recommends cultivating lasting friendships with your customers to gain exposure. Consumers are more likely to purchase from companies they admire and trust, so building a personal brand through authentic and informal UGC content makes you distinguishable and relatable. You can promote your brand persona further by creating employee advocacy programs that allow loyal team members to produce branded content that aligns with their skills and strengths and resonates with your target audience. Testing various social media platforms and analyzing performance data is crucial when developing a robust marketing strategy. In this episode of the Up Arrow Podcast, William Harris sits down with Neal Schaffer, the Founder and President of PDCA Social, to talk about social media and influencer marketing. Neal shares his medical analogy for social media marketing, why he studies the subject, and how to curate content for diverse social media platforms.

Brian Nolan is the Co-founder and CEO of BookOutdoors, a fast-growing platform for planning and booking personalized outdoor getaways. His passion for building beautifully designed products has made him a veteran of the e-commerce industry. As a serial tech entrepreneur, Brian co-founded Suspect Clothing, the HJN Group, Top-Bargains, and Sellbrite — which was acquired by GoDaddy in 2019. In this episode… As the e-commerce industry becomes more prominent in the corporate space, marketing strategies have evolved significantly. B2C businesses emphasize the importance of targeting consumer emotions through convincing storytelling — accomplished through multi-channel marketing techniques. How can your business benefit from multi-channel marketing? eCommerce entrepreneur Brian Nolan believes multi-channel marketing is beneficial for most online retailers. Since customers differ in their preferred retailers, marketing on various channels can broaden your target audience and provide an opportunity to spend less of your marketing budget. Spending less to have a more effective marketing strategy across multiple platforms is helpful for any business looking to gain more traction in the marketplace. Brian’s knowledge of the industry and experience founding e-commerce brands offers encouragement to fellow entrepreneurs.  On this episode of the Up Arrow Podcast, William Harris welcomes Brian Nolan, the Co-founder and CEO of BookOutdoors, to discuss the lessons he’s learned from his entrepreneurial endeavors. Brian talks about the differences in marketing strategies for B2B and B2C brands, the benefits of multi-channel marketing, and the challenges many founders overlook during business acquisitions. He also expresses how leading with empathy equips team members to work toward a common goal.

Aaron Orendorff is the Head of Marketing at Recart, a text marketing app helping businesses grow through personalized AI text messages. He is also the Founder of iconiContent, which provides B2B content strategies to generate qualified leads and scale businesses. As a member of the Forbes Communications Council, Aaron’s literary work has been featured in the New York Times, Mashable, Business Insider, and Success Magazine, among others. Before Recart, he was the Editor-in-Chief of Shopify Plus and the VP of Marketing at Common Thread Collective, an e-commerce growth agency. In this episode… Marketing is designed to communicate with consumers in hopes they purchase your products. SMS messaging is a marketing channel many brands pursue, but the majority do so ineffectively — negating its intended purpose of increasing sales revenue. What SMS strategies should you implement to reach target audiences, and which methods should you avoid? Most brands spend their marketing budgets on mass messaging campaigns — known in the industry as batch and blast — which can be expensive if improperly used. Marketing expert Aaron Orendorff explains that brands can determine SMS campaign success by the amount of new leads added to their messaging list. Finding a messaging cadence and incorporating follow-up messages to consumers who abandon their carts can generate more sales and significantly increase revenue.   On this episode of the Up Arrow Podcast, William Harris welcomes Aaron Orendorff, Head of Marketing at Recart, to discuss why brands struggle to produce favorable results from their SMS marketing strategies. Aaron shares insights on using SMS strategies effectively. He also explains how the five foundational messaging flows improve customer engagement and increase sales.

Brittain Ladd is a globally recognized expert in business strategy, robotics, retail logistics, and supply chain management. As a leading researcher of AI’s impact on global supply chains, he has led the worldwide e-commerce and cross-border expansion and has guided Amazon Fresh’s pantry operations and Amazon’s micro-fulfillment strategies. Brittain advises one of the largest social media platforms on shoppable videos. As a business influencer, he has predicted corporate trends and consumer behavior years in advance, influenced businesses on billion-dollar decisions, and transformed companies by identifying M&A opportunities. Brittain was also a strategic advisor for Instacart and Kroger. In this episode… The e-commerce industry has drastically evolved since its inception in 1969. Now, five decades since its debut, e-commerce brands continue advancing technological boundaries to improve the consumer experience. How will AI integrations affect e-commerce platforms in the coming years? Known for his accuracy in predicting digital trends, Brittain Ladd forecasts the strategies companies will introduce to their operating systems and how incorporating AI into retail and e-commerce platforms will change the trajectory of businesses. Despite the apprehension toward AI’s involvement, its capabilities allow businesses to prioritize operations and customer satisfaction, leading to faster delivery times and sustainable platforms.  On this episode of the Up Arrow Podcast, William Harris welcomes Brittain Ladd, a business strategy, robotics, retail logistics, and supply chain management expert, to discuss the impact of AI on e-commerce platforms and the retail industry. Brittain also provides insight into how hyperlocal logistics cater to customer preferences, Gen Z’s involvement in the evolution of retail marketers, and his solution for reversing the decline in US military recruitment.

Charlie Youakim is the CEO and Executive Chairman of Sezzle, a fintech company on a mission to financially empower the next generation by offering interest-free installment plans for online and in-store purchases. As a fintech founder, Charlie leverages his leadership and management skills to build exceptional companies. Before Sezzle, he founded Passport, a leader in the transportation payments space. In this episode… Many young adults entering the workforce are ready to create a stable financial future, but preparing for a career and building a line of credit is difficult during inflation. eCommerce brands also experience challenges due to the US financial climate. In uncertain times for consumers and e-commerce providers, buy now, pay later programs are an asset for the economy.  Most Americans are not white-collar workers and are ill-equipped with financial resources to help them build credit lines. Innovative solutions to bridge the financial gap are critical for the US economy during a looming recession and inflation. Aware of the opposition affecting the economy, Fintech founder Charlie Youakim helps the e-commerce market and its consumers by providing a buy now, pay later service that promotes financial health for both parties.  On this episode of the Up Arrow Podcast, William Harris welcomes Charlie Youakim, CEO and Executive Chairman of Sezzle, to discuss how his company financially empowers the next generation. Charlie shares why young individuals are attracted to Sezzle’s products, how it builds customers’ credit, and the benefits it offers brand partners. He also imparts wisdom to e-commerce founders on preserving their company through inflation and why dedicating time to team-building is your most valuable asset.

Ted Rubin is a social marketing strategist, international speaker, business advisor, and author. Known for his ability to make personal connections with people, Ted coined the term Return on Relationship™ (ROR) — proposing authentic relationships create value for both parties. His book, Return on Relationship, is based on this premise and presents practical, real-world ideas to help businesses maximize their potential using community-focused internet resources.  Ted is also a strategic advisor, investor, and board member for multiple entities in various industries, including Evergreen Trading, The Coupon Bureau, Impactica, Spaceback, and SheSpeaks Inc. In this episode… eCommerce brands are quickly losing customer interest due to impersonal marketing strategies. With numerous companies selling similar products and services, novel approaches are sparse, making it challenging to distinguish between competitors. Amidst competing brands, how can you personalize your marketing efforts to entice and retain customers?   Mass emails are a leading marketing strategy for many brands because of their convenience. Lack of personalization, however, does little to convince a consumer they are valued. Ted Rubin implores brand marketers to invest in strategies that cultivate a mutually beneficial relationship. Gathering intel on customer preferences and prioritizing their worth will garner appreciation and loyalty — improving a business' reputation. On this episode of the Up Arrow Podcast, William Harris welcomes Ted Rubin, strategic relationship advisor, to discuss how e-commerce enterprises can boost their brand and reputation by valuing return on relationships. Ted’s marketing career provides perspective on maintaining a social media presence and strategies for personalizing the customer experience. He also urges e-commerce businesses to reevaluate the efficacy of their email marketing habits and shift to an omnipresent marketing mindset.

Nathan Hirsch is the Co-founder of EcomBalance, a monthly bookkeeping service helping e-commerce businesses manage their bookkeeping and finances. Nathan began his entrepreneurial journey in 2009 by selling products on Amazon and is best known for his involvement in co-founding Freeeup in 2015. With an initial investment of $5,000, Nathan helped scale the business to $12 million in yearly revenue before selling it in 2019. Nathan is also the Co-founder of AccountsBalance, EcomBalance’s partner company, and the Co-founder of Outsource School, where he teaches business owners proven hiring methods for finding top-tier virtual assistants. In this episode… Finances are the driving force behind any company and indicate operational strengths and weaknesses. Most e-commerce business owners are ill-equipped to read and decipher financial statements, yet they shoulder bookkeeping responsibilities. Taking ownership of financials without accounting knowledge is a risk most entrepreneurs can’t afford. Although hiring a bookkeeper is an additional monthly payment, business owners are relieved from the stress of balancing accounts. Bookkeeping requires understanding accounting principles and allocating time to read and record accurate financial details. Most e-commerce executives can’t commit to recording expenditures amidst their leadership responsibilities. Nathan Hirsch testifies business owners who take financial responsibility are likely to spend more money fixing their mistakes than if they had hired a professional. He implores entrepreneurs to hire a bookkeeper, and, at the very least, review income statements, balance sheets, and cash flow monthly to recognize company trends.  On this episode of the Up Arrow Podcast, William Harris welcomes Nathan Hirsch, Co-founder of EcomBalance, to discuss the pertinence of accurate bookkeeping for e-commerce businesses. Nathan shares common mistakes business owners make when balancing their books, how segmenting books can accelerate business growth, and the three financial reports owners must compare monthly. He also provides resources for hiring vetted CPAs and CFOs to transcribe budget data.