SPOTLIGHT: How Josh Guttman Landed Investors for SELLIT9 by Being Himself
Feb 13, 2025
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Josh Guttman, co-founder and CEO of SELLIT9, shares insights from his extensive experience in SaaS sales and his transition to entrepreneurship. He reveals how he navigated the challenges of fundraising, learning that VCs seek belief and connection over hard sales tactics. Josh emphasizes the power of authenticity and storytelling in his successful pre-seed round. He also discusses the resilience needed in the entrepreneurial journey and details SELLIT9's innovative tech marketplace, allowing Canadians to sell devices for cash.
Josh Guttman's transition from sales to founding SELLIT9 taught him that fundraising requires authenticity, not just traditional sales tactics.
The innovative approach of SELLIT9 addresses consumer pain points in electronics trading, leveraging unused devices directly at checkout for purchases.
Deep dives
Navigating the Journey from SaaS to Startup
Josh Gutman shares his transition from a successful career in SaaS, including roles at Salesforce, to founding his own startup, Sell at 9Pay. With over 20 years of experience in technology and sales, including being one of the first SDRs at Salesforce, he reflects on how this background provides a unique perspective on startup challenges. The conversation highlights the initial hurdles of launching a company that allows consumers to trade in unused electronics for purchases, particularly at checkout. Gutman emphasizes his focus on solving real-world problems, driven by personal experiences as a parent trying to manage family technology efficiently.
Innovative Trading Platform for Electronics
Sell at 9Pay aims to simplify the process of trading in electronics by allowing users to leverage the value of their unused devices directly at checkout for purchases. Gutman discusses the complexities involved, including the need for instant valuation technology and a network of buyers who refurbish and resell items. Unlike traditional marketplaces, this platform addresses consumer pain points, such as scams and the hassle of dealing with unknown buyers. This innovative approach not only provides value to consumers but also has the potential to disrupt how electronics are sold in the marketplace.
The Art and Science of Fundraising
Gutman shares insights from his fundraising journey, underscoring the differences between B2B sales and attracting venture capital. He identifies the need to create a 'fear of missing out' among investors and highlights the importance of authentic storytelling, while balancing conciseness and impactful communication. Feedback from early meetings urged him to tone down his natural salesmanship, prompting a deeper reflection on how to present himself authentically without alienating potential investors. Ultimately, his experience underscores the importance of being genuine while also understanding the unique mindset of VCs in a crowded marketplace.
Fundraising isn’t just sales—something Josh Guttman, co-founder and CEO of SELLIT9, learned the hard way. After spending years in SaaS sales and leadership, including a 12-year run at Salesforce, Josh thought his natural ability to pitch and build relationships would give him an edge in raising capital. But he quickly discovered that VCs don’t want to be sold—they want to believe.
In this episode of Topline Spotlight, Josh shares his journey from seasoned sales leader to first-time founder, the unexpected feedback that forced him to rethink his approach, and how he ultimately closed his pre-seed round by striking the right balance between confidence, storytelling, and authenticity.
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