Before launching Small Business Diaries we had a simple goal - find a way to share the stories and insights of influential business leaders with our customers.
It was an opportunity to share their stories and offer insights into all the elements that make up small businesses - from leadership struggles, conceptualizing a business in the first place, encouraging growth, and building customer loyalty.
But like most projects, it came with surprises and challenges that often left us with a completely different perspective of our guests and businesses in general.
So, we sat down with the hosts Jon and Steve, and asked them to reflect on what we’ve learned during this journey and the key moments that have stayed with us.
You can find all the episodes of Small Business Diaries here.
1. Sales is the foundation of founder-led success
Founders are the driving force behind any business, often leading company sales efforts by placing themselves as the face of the organization.
In the early stages, they’re usually responsible for pitching to new clients, managing customer relationships, and closing new deals.
Steve explains: “Unlike larger companies where responsibilities are divided among specialized teams, small business founders often find themselves deeply involved in day-to-day operations, including sales.
“Instead of just managing, they're actively executing things on an operational level. Ultimately, they're out in the field, working to win business themselves, which is incredibly valuable.”
No matter your business or industry, sales is still the number one priority for founder-led businesses. Why? Because sales is more than just a function, it’s simply about survival. Without consistent sales, you have no capital to fuel your growth, this hands-on approach is necessary, especially when resources are tight and every deal counts.
There are other options of course. Founders without a classic background in sales may look for alternative approaches that better suit their skill sets. Steve adds:
“Some founders aren't involved in sales, they instead focus solely on product, relying on Google, social media, or, contacts in their industry to get their business out there.
But most people we’ve spoken with are coming from a sales angle first.
2. Vulnerability is a powerful leadership tool
Something that surprised both Jon and Steve was the guest’s ability to be vulnerable about their career journeys. Everyone was honest about the mistakes they made early in their career that not only helped them learn but also, guided their decisions later on.
When senior leaders open up about their struggles it creates a sense of connection and relatability. It breaks down the myth that leadership has all the answers and instead fosters confidence among those who look up to them.
Jon said: “What I found most interesting in the episode we recorded with Andy was that it wasn’t focused on sales, but more about leadership.
“Listening to two senior leaders openly discuss their challenges made me realize that even very successful people face the same struggles as the rest of us. It humanized them and made me feel more confident in myself.”
This insight has shown us that being open about setbacks and personal challenges doesn’t diminish credibility, if anything it strengthens it. Vulnerable leaders inspire trust and create a more inclusive and authentic work environment.
Steve also recognized this trend: “In Julia’s episode, she highlighted how important it is to ask experts for help. Small business owners often feel like they have to wear every hat, and while that’s sometimes necessary, there’s real value in getting advice from people who truly know their stuff.”
3. Adapting sales strategies in a digital world
Sales tactics are constantly changing. Consumers are becoming more aware of the products they’re buying, so instead of relying on salespeople to educate them on products, they're doing their own research. This means businesses have to look for new ways to stand out in their industries.
Steve said: "When talking to guests we’re seeing an evolution in how businesses communicate with prospects. Sales methodologies are constantly changing and as a business owner, you need to adapt to these shifts.
“A big trend right now is using social media to effectively drive sales, but as everyone adopts the same strategies, the landscape becomes saturated, forcing further evolution.
“Outbound models used to rely heavily on emails or cold calls, but now it's about balancing multiple approaches like email, calls, events, and especially social media. Founders, in particular, must be active on social to engage their audience.”
Despite these changes, the core principles of sales remain the same. While methods evolve, the foundational elements still hold value for any salesperson or business owner.
Jon added: “When we spoke to Morgan, I agreed with his view that sales professionals naturally evolve into content creators. However, like Steve, I’ve noticed the oversaturation of social media, and I’m feeling similar to how we grew tired of email bombardment.
“Just as car salespeople now simply facilitate purchases, the role of CEOs in social selling has become common. So, what's next when we tire of social media? One thing is certain: whatever comes next will still involve people, because people always buy from people, not faceless entities."
4. The continuing role of AI in sales
AI is a topic that everyone is talking about. It become accessible in recent years and if you’re not using it to streamline your workflow processes chances are you’re falling behind your competitors.
AI is reshaping how businesses approach sales, from automating outreach efforts to improving customer engagement.
Steve explains: “AI is becoming a major force in sales, and we shouldn’t underestimate its impact. As a CEO, I constantly hear ‘businesses must adapt to AI or risk falling behind.’
“This isn’t an exaggeration, many are already leveraging AI in areas like outbound sales and chatbots, and its usefulness will only continue to grow.”
AI has transformed sales by automating manual and time-consuming tasks, such as handling large volumes of customer inquiries through automated services.
The technology has made sales teams skip manual time-consuming tasks like we detailed above, so they can spend more time on the human-to-human part of selling, and managing client relationships.
While small businesses don’t have the resources larger companies have, integrating AI into their sales strategies can give smaller sales teams an advantage.
5. Personal growth through podcasting
Hosting the show has helped Jon and Steve learn both personal and professional lessons. Not only have they learned from their guest’s experiences but actually hosting the podcast has encouraged personal and professional growth.
Jon noted that the process has improved his interviewing skills.
He says: “A good example would be when I asked Julia about her motivation for starting her Stronger Together group. Instead of just hearing the story of how she built the group I was compelled to dig deeper and identify the motivations behind setting it up in the first place.”
Adaptability and resilience have also been a recurring topic in many of the episodes. It's shown the hosts that there is no clear path for building a business and everyone’s journey to success is different.
Every guest has shared a story where they’ve come up against a challenge, but they allfound a new way to adapt their business to overcome these issues.
Jon explains: “Andy leveraged his network, Morgan built a smaller more agile team when facing pipeline challenges - it’s shown us that there’s no single path to success - what matters is a willingness to evolve and grow with your company.”
The hosts have also noted that curiosity and a willingness to admit when you don’t have all the answers is another crucial trait for success. Steve explains: “The business leaders we’ve had on the show are extraordinary individuals with ambition and drive.
“Many leaders feel they need to act as if they have all the answers. It's okay not to know everything as long as you’re honest and committed to finding solutions.”
Key takeaways
- Sales is a facilitator for success: Founders are heavily involved in sales, often driving growth by being the face of their business. Closing deals is crucial for survival, especially when resources are limited.
- Vulnerability as a leadership tool: Vulnerability is a powerful leadership trait. It helps to build trust and makes them more relatable enhancing their credibility.
- Creating new digital sales strategies: Traditional outbound models should be complemented with digital and social media approaches. However, you need to consider new ways to adapt to them.
- Utilizing AI in Sales: AI is crucial for automating customer outreach and handling enquiries allowing small businesses to stay competitive and focus on value-added activities like relationship building and deal closing.
- Personal growth: Hosting a podcast has allowed both Steve and Jon to develop their interviewing skills and helped them discover new approaches to both business and life. The guests have taught them lessons on adaptability, curiosity, and the willingness to admit when one doesn't have all the answers, showing that there is no single path to success.
Would you like to appear on Small Business Diaries?
Small Business Diaries offers a valuable, behind-the-scenes look at the realities of running a small business. From the importance of sales and constant innovation to the impact of authentic leadership and the evolving role of AI, the show provides insights every business owner can use.
Want to share your own story? We're always looking for passionate guests eager to inspire others with their journeys. If you’d like to participate, please fill out our interest form.
If you’re looking to hear more motivational stories from influential entrepreneurs, don’t miss the next episode of Small Business Diaries. Find us on YouTube, Spotify, or Apple Podcasts, and join us as we delve into the journeys of business leaders and the lessons they've learned along the way.
