Five Email Newsletters Every Business Leader Should Subscribe To
The 2020s has been called the age of the email newsletter, and for good reason. For business leaders, these newsletters are a valuable way to stay informed, inspired, and ahead of industry trends without scouring the internet. Many of them, much like the podcasts we highlighted in our “Tune In And Cash In: 3 Podcasts You Should Listen to Before Selling Your Business” blog from September, are also free.
Plus, there are a multitude of options for those who like to receive their knowledge in this manner. In the business category alone, there have been over 365 million newsletters launched on LinkedIn since 2017. This is, ostensibly, a good thing. It makes finding and reading relevant content more convenient than ever by providing insight into industry trends, stories, information, and expertise that is delivered straight to your inbox. But with the riches also come the spoils. And while each of those 365 million newsletters may contain valuable information, most of us don’t have time to read millions of newsletters a day. We have to be a bit discerning about which subscriptions are worth our time. Luckily, we vetted the top twenty-five business-related email newsletters and found five that we think that we think are more than worth your time. So, without further ado, here are five email newsletters that EVERY business leader could benefit from subscribing to. They are…
With over four million subscribers, this is one of the most popular email newsletters out there, so if you don’t already subscribe, you should. The schtick behind this one is that each of the daily emails from The Morning Brew offers updates about the business world that can be consumed in just five minutes (or the length of time it takes you to drink a cup of coffee).
James Clear, the best-selling author of Atomic Habits, takes a unique approach with his weekly newsletter, which is also a five-minute read. In each installment, Clear delivers three ideas, two quotes, and one question worth pondering. The result is something more thought-provoking than pedantic, making reading 3-2-1 a great (and quick) way to shake off the brain fog that comes with the work week and prompt yourself to think outside the box.
Perhaps the most technical newsletter we have on this list, Term Sheet offers daily news and analysis related to private equity, venture capital, start-ups, mergers and acquisitions, and high-value deals. These reads can trend slightly longer (more like ten minutes than five), but they contain gold standard content produced by Fortune. Additionally, each issue features an updated list of venture and private equity deals, exits, and funds.
What we love about this email newsletter is that it focuses on the mental side of business success, covering topics such as personal productivity and well-being. It is released weekly and put out by Jason Feifer, who also serves at the chief editor of Entrepreneur magazine. In it, Feifer shares useful and actionable tips on how to be more “successful and satisfied” in both business and life. If you’re looking to lead with confidence while staying grounded, this weekly read is for you.
This one is HR specific, but since HR is the foundation of any good company, and since we love and trust the woman behind this newsletter, we wanted to include Workology on this list. Produced by veteran entrepreneur Jessica Miller-Merrell, this weekly newsletter focuses on HR topics like leadership and recruiting, providing advice that is simultaneously timeless and disruptive.
Of course, there are so many great email newsletters out there. (We certainly had trouble whittling the list down to five.) If you prefer learning through this format, it’s also worth conducting a quick search to see which email newsletters are particularly popular or useful to your current business needs. Whatever those needs are, you will find a newsletter that addresses them.
However, the newsletters listed above are a great place to start! Each provides insightful, thought-provoking, and even entertaining content that might have you actually looking forward to opening your inbox at the start of your work day.
Stay Connected with Our Strategic Partners
In addition to these excellent newsletters, don’t forget to explore the insights and resources shared by our Strategic Partners. From IT and insurance to finance and HR, they provide valuable knowledge tailored to business leaders.
If you’re interested in subscribing to their newsletters, please contact us or reach out directly to the Strategic Partners. In the meantime, you can access their expertise through the resources available on their websites:
EFBC Welcomes a New Team Member
Olivia joined EFBC last month as a Marketing Coordinator.
1. What drew you to EFBC, and what excites you most about joining the team?
EFBC stood out to me because of its close-knit team and extensive, strong community. I’m looking forward to working alongside dedicated colleagues and contributing to their impactful work and mission.
2. Please tell us a little about your professional background and what you hope to bring to EFBC.
I graduated from the University of Illinois at Urbana-Champaign with a BS in Advertising and a BFA in Graphic Design. Loving design and strategy, I found my place in marketing, working on marketing and design projects for all different types of companies.
Starting my own business has always been a dream and last year it finally came to fruition. Inspired by my love of design and Chicago’s many vintage stores and markets, I started a business selling vintage clothing and jewelry and joined three vintage collective brick-and-motor stores in the city.
I’ve long admired entrepreneurs and their ability to forge their own paths, and launching my own business has only deepened that appreciation. At EFBC, I’m excited to bring a fresh perspective to our marketing efforts and to help grow and strengthen our community of business leaders and entrepreneurs.
3. In your spare time, what do you like to do for fun?
I enjoy exploring the city and discovering new shops and neighborhoods. Living in Wicker Park, I especially love rollerblading and running on the 606 during the summer.
4. What is your go-to karaoke song?
“Since You Been Gone” by Kelly Clarkson.
2024-2025 Tax Planning Guide
Brought to you by Cray Kaiser
To keep your taxes to a minimum, you first need to be aware of all of the tax breaks for which you’re eligible. Then you have to implement strategies that allow you to take maximum advantage of those breaks and other tax savings opportunities while staying in compliance with tax law. You also can’t forget about the massive Tax Cuts and Jobs Act (TCJA) that generally went into effect six years ago but still significantly impacts tax planning. Many of its provisions are scheduled to expire after 2025, and it’s uncertain whether they’ll be extended. There may be actions you can take this year to help lock in tax savings. Finally, you need to keep an eye on Washington, because the outcome of the 2024 elections will have a big impact on taxes in the future.
This guide provides an overview of some of the key tax provisions you need to be aware of. It offers a variety of strategies for minimizing your taxes in the current tax environment. Use it to identify the best ones for your particular situation with your tax advisor, who also can keep you apprised of any new tax law developments that might affect you.
Click here to read the full guide
The Personal Touch: Creating Personalized Customer Experiences at Scale
In a recent survey conducted by Epsilon, 80% of consumers expressed that they are more likely to do business with brands that offer personalized experiences. This is believed to be a direct result of the internet and e-commerce: as personalized products and services become more accessible in our increasingly connected society, customers are starting to expect and demand a certain level of “personal touch” in the ways in which they interact with brands and companies. However, even though 85% of companies think they offer the type of personalization their clientele is looking for, customer surveys show that only 60% of businesses actually achieve this goal. There’s clearly a discrepancy there, and many experts think it can be explained by one thing: scale. Of course, it’s relatively easy to offer personalized experiences when your business is small or just starting out. Creating relationships with hundreds of people is far less time consuming than maintaining those relationships at the same level with hundreds of thousands of people. As your company grows, it’s natural to cut back on that “personal touch” in what you feel are small, imperceptible ways, but the data tells us that your patrons are feeling those cutbacks all the same. So the big question is: How do you achieve your growth goals while maintaining the personal touch that created your loyal customer base in the first place?
Embedding Customer-Centricity as a Core Value
The answer to that question is multifold, but it starts by embedding customer-centricity into your organization’s operations and values. (If you’re looking for advice on how to do that, check out our recent blog post on .) From there, the expert recommendation to small businesses faced with scaling up is to automate when and where you can. While automation may seem like it runs counter to the goal of creating personalized experiences, the reality is that automation allows you to plan ahead and create recurring touchpoints like emails, blog posts, social media updates, and offers or promotions tailored to specific customers.
For an example of how this works in practice, look at a company like Chipotle, which operates worldwide on a huge scale. By automating their text interface, they created a platform where they can blast their customer-base with promotions related to everything from Teacher Appreciation Week to Halloween. And their promotions work. Not only do these blasts have the benefit of increasing Chipotle’s sales up to four times (depending on the promotion), but customers cite them as something they appreciate about the brand. It may seem like a small thing, but a teacher getting free guacamole with her order on a week that is meant to honor her profession is the kind of “small thing” that is proven to make a giant company feel like it operates on a personal level.
Scaling with a Personal Touch in Family and Entrepreneurial Businesses
The other essential element growing businesses need to have in place to continue to operate with that “personal touch” is customer service. This includes everything from sales to help hotlines. Scaling up may require owners and managers to delegate these and other tasks, empowering their employees to engage with the customer base in ways that previously happened at a higher level. While this can feel like sacrificing control, it’s actually a good thing! The fact that your company is growing means you can’t possibly engage with everyone who interacts with your brand in a meaningful way. But a well-trained and empowered outward-facing workforce means that your business can be reachable, even when you are not. That being said, if you are face of the brand your built, you do want to retain visibility to your clientele in some manner. For family businesses, this delegation may also include close-knit family members or longtime employees who share a deep understanding of the company’s mission and culture.
Delegating and empowering your workforce doesn’t mean disappearing behind a curtain like the Wizard of Oz. While this visibility looks different for different owners and CEOs based on their personalities and the nature of their companies, some tried and true methods include weekly (or monthly) blog posts, a robust presence on your company’s social media pages, newsletters, and seasonal communications. For small and mid-sized businesses, highlighting the story behind the business – its family history, entrepreneurial journey, or milestones, can foster a deeper emotional connection with customers. However, you choose to stay in your customers’ consciouses, make sure to share your successes as you grow! If they’ve been with you from the beginning, chances are they’ll be thrilled to see you taking off!
Conclusion
For family and entrepreneurial businesses, scaling up is both a challenge and an opportunity. Embedding customer-centric values, embracing smart automation, and empowering your team ensures you can grow sustainably without sacrificing the personal touch that made you successful. Additionally, don’t be afraid to lean into your strengths – whether that’s community involvement, family values, or your personal leadership style. Customers appreciate authenticity, and sharing your journey can inspire loyalty and engagement.
Stay visible, stay connected, and let your shared experiences inspire your continued growth.
EFBC President’s Message: Core Values at the Negotiation Table
Dear EFBC Members,
I am back with another themed letter, and this time I am thinking about Negotiations, and specifically how they are guided by Core Values.
Negotiations are a core part of any business leader’s role. Whether it’s a high-stakes contract or a simple agreement, we all bring to the table a toolbox of strategies—understanding our BATNA (Best Alternative to a Negotiated Agreement), leveraging data, and staying prepared. But beyond tactics and strategies lies a deeper dimension of negotiation: the alignment with our values.
In the pursuit of a win, our competitive energy as entrepreneurs can be activated, and it’s easy to focus on the tactical and analytical aspects of negotiation. However, the most meaningful and sustainable agreements often come from a softer, values-driven approach. This means prioritizing respect, empathy, and integrity throughout the process.
I am currently working through a high-stakes negotiation around potential M&A for my business. I know the tactics, and I know the data, so I am well-positioned. But I also keep re-visiting both the core values for my business and my personal principles. I am actively seeking to avoid an outcome where I have “won” but caused myself future harm by straying from what has served me well to-date.
As you go through the inevitable negotiations in your businesses, I encourage you to leverage the EFBC way of emotional intelligence, and the support of your forum and the broader EFBC community to help you stick to your personal values.
Warm regards,
Darrin Shillair – EFBC President 2024-2025
Powerful Conversations, Powerful Takeaways
Two weeks ago, we hosted our 2nd annual Strategic Partner Night of Knowledge, bringing together the expertise of our strategic partners to discuss topics crucial to today’s business landscape. This year, we were thrilled to welcome two new partners, Wintrust and PSM Partners, who contributed fresh perspectives to our collaborative roundtable discussions. Members, prospects, and guests gathered around the tables to hear each partner’s insights, sharing experiences and gathering actionable takeaways. After the roundtable discussions, everyone enjoyed a fantastic dinner, where the conversations kept flowing and connections grew even stronger.
Here’s a snapshot of the night’s invaluable discussions:
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ALERA Group: Marcus Newman – Vice President
Marcus tackled the challenges businesses face with an aging population within their health plans. He emphasized the need for diverse insurance options that cater to various needs such as PPOs, HMOs, QHDHP, including specialized plans for chronic conditions. He also stressed the importance of educating employees about Medicare and Medicare Advantage through open enrollment meetings, webinars, benefits internet site, etc). For larger businesses (>50 employees), leveraging negotiations with insurers can help manage costs, while maintaining compliance with federal laws like the Age Discrimination in Employment Act (ADEA) ensures fair treatment for all employees.
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ODEA: Patty Rioux – President and JJ Lattea – Technical Marketing Manager
Patty & JJ explored the topic of AI, the evolving role of Large Language Models (LLMs) in business. The discussion highlighted 3 primary ways to work with LLMs, including techniques like prompt engineering to maximize their effectiveness. Key strategies for prompt engineering included few-shot learning, where a few examples help guide the model; chain-of-thought, which prompts the model to tackle problems step-by-step; and self-consistency, which ensures consistent outputs across different runs. They also discussed real-world applications of AI tools like Microsoft Co-Pilot, which ODEA used to create their podcast Why Brand Matters in M&A.
EFBC will be hosting an AI Workshop Breakfast Club in March 11, 2025 with strategic partners ODEA and PSM, offering a deeper dive into the impact of AI on business. Mark your calendars!
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Cray Kaiser: Deanna Salo – Managing Principal
Deanna shared key insights on preparing for a successful business sale, emphasizing the importance of planning, organization, and readiness for disruption. First, ensure all owners are aligned on goals and prepare emotionally for the transition, which can take months. Limit sharing sensitive financials until an NDA is in place, and carefully navigate the letter of intent, focusing on key deal terms like sale structure, purchase price allocation, and due diligence timelines. Get your financial house in order: audited statements, clear internal controls, and a solid organizational chart are essential. Finally, time your sale strategically, considering seasonality and post-tax cash flow, while identifying potential buyers within your network.
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Burke Law: Eric VanderPloeg – Partner
Eric shared ten essential tips to help businesses avoid costly litigation. Start with strong foundations: keep governing agreements up to date, manage credit risks, and use well-crafted sales forms. Limit liability and disclaim warranties wherever possible, and ensure your employee policies and handbooks are rock solid. Protect proprietary information, understand data privacy obligations, and include smart litigation clauses in contracts. Lastly, invest in the right insurance to cover your bases. By addressing these key areas, you can focus on growing your business without the worry of costly legal battles.
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Private Vista: Greg Bogdan – Senior Advisor, CFP
Greg shared a powerful giving tool: Donor-Advised Funds (DAFs). Think of a DAF as a charitable investment account that grows tax-free, simplifying your philanthropy while offering generous tax benefits. You can contribute cash, appreciated assets, or even limited partnership interests, maximizing deductions and avoiding capital gains taxes. With DAFs, you control when and where to donate, while the fund sponsor handles the admin work, from verifying charities to tracking grants. Plus, you can create a lasting legacy by naming a successor to continue your charitable vision. A smart, flexible way to support causes close to your heart!
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Psyched: George Karavattuveetil – President & Founder
George emphasized the growing value of flexible, holistic employee benefits. In an evolving job market, companies are focusing on benefits that promote financial security, career mobility, and personal well-being. Benefits such as flexible work arrangements, development opportunities, and financial wellness programs are more valuable than ever for attracting and retaining top talent. Employers who prioritize these benefits are seeing increased engagement and loyalty from their workforce.
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PSM Partners: Mike Mete – Founder and Jon Pisani – Senior Engagement Manager
Mike and Jon delved into the critical importance of Cybersecurity, Data Governance, and Risk Analysis, offering valuable insights on how businesses can stay ahead of emerging threats. They highlighted the significance of conducting thorough cybersecurity risk assessments, which help organizations identify potential vulnerabilities, allowing to strengthen their defenses and reduce risks. In today’s digital landscape, proactive risk management isn’t just an option – it’s a must. With the growing reliance on data, they stressed the need for strong governance practices to safeguard sensitive information and ensure compliance with evolving regulations. For more insights and resources on cybersecurity, visit PSM Partners’ Cybersecurity resources.
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Wintrust: Matt Hammer – Division Manager, SVP and Pat Stoltz – President (ESOP Finance)
Matt and Pat shed light on the powerful benefits of ESOP – a powerful tool for business owners looking to sell to employees and preserve the legacy of their companies, explaining how it can be a game-changer for both business owners and their employees. They highlighted the tax advantages, such as the potential for 100% S-Corp ESOPs to be exempt from federal taxes and the opportunity for C-Corp ESOP sellers to defer capital gains through a 1042 election. ESOPs also offer flexibility by allowing partial sales, enabling owners to ease out of the business over time while still staying involved. Wintrust’s expertise in ESOP financing helps guide companies through the process, from structuring the deal to completing the transaction
To wrap up, we couldn’t have said it better than our Strategic Partner Jon Pisani from PSM Partners, who captured the true essence of Empower Night:
“Tonight is a great example of feeling very supported by the Community and being able to share institutional knowledge. Providing that level of insight empowers me as a proud EFBC member. Sharing that information with everyone – it’s just a great feeling for life.”
Here’s to many more nights of knowledge, connection, and empowerment!
Meet Drew Hill, Operations Manager at Specialty Sales LLC
- Company: Specialty Sales LLC
- Position: Operations Manager
1. Can you tell us a little bit about yourself, both personally and professionally?
I’m Drew Hill, and I’m currently the Operations Manager at Specialty Sales. I’ve been with the company for three years now, and I’m 29 years old. My role here involves a bit of everything – implementation, support, and leading. My strength lies in understanding the interconnectedness of all operations and keeping everything running smoothly. I got to where I am because I’ve always hated hitting ceilings in my career. I was in a previous role where I realized I was doing all the responsibilities of an operations manager without the title or compensation, and I knew it was time to make a change. That’s when I met Darrin Shillair, and we were on the same page from the start. Now, here I am, thriving in a role where I can continuously grow.
2. What do you like the most about what you’re doing right now?
There are two things I really enjoy about my role. First is problem-solving. I love using logic and figuring things out, which keeps me mentally stimulated. The second thing I value most is the freedom that comes with the job. Whether it’s financial freedom or just being trusted to get the job done without someone breathing down my neck, it motivates me. That autonomy is what drives me to push for even more freedom.
3. How did you first hear about EFBC?
I first heard about EFBC through Darrin, my boss. He mentioned a leadership program led by George Karavattuveetil and suggested I try it. The program aligned with the leadership responsibilities I was already taking on, so I jumped in. Darrin was the one who connected me to EFBC and their programs.
4. Can you share your experience and any takeaways from the leadership course?
The biggest takeaway from the leadership course was learning to trust my gut. George helped validate that I was already on the right path, especially when it came to team accountability. I had been implementing many of these lessons at work, but the course gave me the confidence to keep trusting my instincts.
5. Can you talk about taking the next steps from participating in the course to attending Forum Flex?
After the leadership course, Darrin suggested I join the Flex Forum group. I’m the kind of person who never says no to opportunities, so I went for it. It’s been a really fulfilling experience so far, and I’m glad I took the plunge.
6. Anything you would like to share that you have taken from your experience in Flex Forum so far?
Flex Forum has been a great way for me to recharge. It’s refreshing to be around smart, thoughtful people, and it forces me to sharpen my perspective. I’ve become better at looking at situations from multiple angles, which has helped my decision-making process tremendously.
7. Do you have any passions or hobbies outside of work?
I’m really big on decompressing after work. I like going to the gym, but I also love my downtime. After a busy day, there’s nothing better than relaxing and unwinding. It’s important for me to recharge so that I can be at my best.
Join us in welcoming Drew Hill to the EFBC community! Members can log in and connect with Ben via the EFBC Member Directory.
EFBC President’s Message: Keep Calm and Persist On
Dear EFBC Members,
I am back with another themed letter, and this time I am thinking about Persistence.
I often feel in my business that my efforts aren’t working, and we’re not making enough progress on our goals. As owners, we are all too familiar with the days where it feels like every effort is hitting a wall, with no immediate results in sight. These days can be discouraging, but they are part of the larger journey. Success isn’t measured by the wins of a single day; rather, it comes in chunks, often appearing when we least expect it.
It’s easy to become impatient when we don’t see instant results. However, persistence is what separates those who build lasting businesses from those who give up too soon. By continuing to put in the effort day after day—without immediate reward—you are laying the groundwork for those eventual “chunks” of success. It’s the accumulation of small, persistent efforts that leads to significant breakthroughs.
As leaders, we must remind ourselves that the road to success isn’t linear. The key is to stay focused on the long-term vision, even when daily progress seems minimal. The challenge is to remain committed to your goals, and trust that persistence will pay off, as it always does. In time, the small efforts compound, and the big wins start rolling in.
The EFBC provides a unique and critically important environment for persisting through the lulls where it feels like your efforts are “two steps forward, one step back”. Our forums and the broader organization are full of leaders who have “been there”, can ground our individual impatience in wisdom, and provide the encouragement needed to Persist.
I wish you all strength in your Persistence through your business and personal challenges faced every day. As the recent recipient of a few step-change chunks of progress, it ultimately can pay off.
Warm regards,
Darrin Shillair – EFBC President 2024-2025