In a recent episode of The Shades of Entrepreneurship, I had the pleasure of sitting down with Jason Greenwood, founder of Greenwood Consulting and an expert in e-commerce and digital transformation.
Our conversation delved into the evolving world of business automation, the power of relationships, and the importance of operational efficiency.
Here are some of the key takeaways from our discussion that every entrepreneur and business leader can learn from: Key Business Lessons from Jason Greenwood of Greenwood Consulting on The Shades of Entrepreneurship
Embrace Automation to Scale Efficiently
Jason emphasized the critical role that automation plays in scaling a business. As operations become more complex, automating tasks not only improves efficiency but also reduces human error.
Whether it’s digitizing customer interactions or streamlining internal processes, automation can save time, reduce costs, and enable your team to focus on higher-value activities.
Jason explained that by leveraging digital tools, businesses can reduce reliance on manual operations and create a smoother customer experience. In his experience, many brands that initially resist automation eventually realize the immense benefits—saving time, eliminating bottlenecks, and removing friction from their sales funnels.
If you're not already considering automation as part of your growth strategy, now is the time to explore it.
Example: I design and automate The Shades of Entrepreneurship apparel through Printful (shop here!), which allow users to create custom designs that are printed and shipped automatically when orders are placed.
Automating this process saves on operational costs, storage, warehousing fulfillment, and other business services that are needed to run an apparel brand.
Data and Digital Systems Build Trust
One of Jason’s most powerful points was how digitization builds trust with customers. In industries like healthcare and e-commerce, access to real-time data is essential. When businesses provide transparency—whether through order tracking, up-to-date product information, or customer portals that simplify account management—they build trust with clients.
This transparency allows businesses to align their operations more closely with customer expectations, leading to better customer experiences and, ultimately, loyalty. Jason noted how even skeptical clients, initially resistant to the term "e-commerce," are more than willing to embrace it when they realize how much easier digital systems make their lives.
The best example I can think of is stock market trading platforms, like Robinhood, WeBull and Fidelity where brokers need immediate updates on stock prices and market fluctuations to make informed decisions and execute trades as quickly as possible, potentially maximizing profits and minimizing risks
Strengthen Relationships with Vendors and Partners
A recurring theme throughout our conversation was the importance of building strong relationships with vendors and partners. In both the healthcare and business world, successful growth often stems from collaboration.
Jason encouraged entrepreneurs to bring suppliers and vendors into their strategic discussions. By doing so, both sides can scale more effectively and find mutually beneficial opportunities.
If you think you're a thought leader, put your ideas out into the world and let the market decide.
An example he shared was how some startups have even secured funding through strategic vendor relationships, allowing them to continue using essential services while managing their financials. Open communication, transparency, and mutual growth are key to fostering these relationships.
Be Ready to Scale Thoughtfully
Jason also warned against scaling too quickly. While growth is exciting, it can also lead to operational chaos if not managed properly. Automation and efficiency are vital to scaling, but it's equally important to focus on building a foundation that can support that growth.
Whether you're expanding into new markets or increasing product offerings, be sure to have the necessary systems in place to handle the additional workload.
A thoughtful approach to growth—one that balances innovation, efficiency, and relationship-building—is essential to avoid overwhelming your team and resources.
One of our cohort members from our Latino Founders business accelerator ran into a similar issues scaling too quickly and almost ran out of cash do to the overbearing cost of operations to scale. Eventually the team scaled their business down and is very successfully in the Pacific Northwest with aspiration of once again scaling nationally, albeit tactfully this time.
Put Your Ideas Out There
One of my favor quotes from my conversation with Jason: If you think you're a thought leader, put your ideas out into the world and let the market decide.
Inspired by Gary Vaynerchuk, Serial Entrepreneur, Chairman of VaynerX, CEO of VaynerMedia, CEO of VeeFriends, & 6X NYT Bestselling Author - that Gary Vaynerchuk, Jason shared how he began sharing his thoughts on e-commerce and digital transformation long before starting his consulting business.
His early willingness to share knowledge helped him establish credibility and grow his brand.
For those in the early stages of building a business or personal brand, Jason's advice is a reminder that success often begins with simply contributing your insights to the conversation.
Whether through blogs, podcasts, or social media, sharing what you know can help build your authority in your industry.
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Jason Greenwood's insights into operational efficiency, digital transformation, and the power of relationships offer valuable lessons for entrepreneurs at every stage of their journey. To dive deeper into these concepts and hear more about Jason’s personal story, I encourage you to listen to the full episode of The Shades of Entrepreneurship.
Stream all episodes on The Shades of Entrepreneurship and gain practical knowledge to help you grow your business.
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