Kevin Chern serves as the CEO of Sanguine Strategic Advisors in Chicago, Illinois. He delivers sustained results to small businesses seeking ways to develop sustainable, revenue-driven growth. Handling issues in operations, financial management, and compliance, Kevin Chern works with clients to invest in their success.
From 2005 to 2010, Kevin Chern was the president of Start Fresh Today, where he helped clients navigate the bankruptcy process. His comprehensive solutions considered the input of the debtor attorneys, consumers, trustees, and agencies.
Kevin Chern subsequently led InfraStrategy, where he offered consumers bankruptcy law solutions. His other areas of focus included lemon laws, class action suits, workers’ compensation, DUI, and personal injury matters. As a co-founder of UpRight Law, he worked with disadvantaged consumers to provide access to legal services.
Beyond Sanguine Strategic Advisors, Kevin Chern is the managing partner at Biz Head Law. At this firm, he offers dedicated compliance and tax services.
What is your typical day, and how do you make it productive?
A typical day involves speaking with business owners, listening and identifying the root causes of challenges in their businesses and recommending solutions. I make my day most productive by finding ways to have as many conversations with them as possible.
How do you bring ideas to life?
Ideas are brought to life by taking a series of iterative steps. Each step is an opportunity to explore a bit further whether or not the idea has merit and deserves further investment of time and energy. Each step is also an opportunity to refine the original concept.
What’s one trend that excites you?
As cliché as it is, the growth of Artificial Intelligence and its various applications to almost every aspect of business and personal life are truly awe inspiring.
What is one habit that helps you be productive?
As much as possible, I block personal time on my schedule. Each day from 11am to 1 pm and then from 5pm to 6pm I block my calendar so no one can schedule a call or meeting for me. I use that time to catch up on email, work on projects that require dedicated attention, exercise, take a walk or take a short nap. It’s labelled “Personal Time” on my calendar and the dedicated time makes a huge difference to my productivity and balance.
What advice would you give your younger self?
Think very carefully where a new business venture is going to take you a year or two out. We tend to get very excited about a new opportunity or business endeavour, but often fail to consider what impact it will have on our happiness a year or two later, as it starts to scale (or doesn’t). Some of my greatest business endeavours turned into businesses that, although economically successful, made me not enjoy going to work every day and regret ever having started the business. I pursued those business ideas because I knew they could be successful and that I could execute them, but did not consider the other ways that operating the business would negatively impact me. If I had a “redo”, I would ask myself how each business would lend itself to fulfilling my personal happiness and give me satisfaction in my work-life balance.
Tell us something you believe almost nobody agrees with you on?
I believe that making introductions to people in one’s network for compensation is a positive thing and doing so does not detract from the goodwill one conveys by making the introduction. My belief challenges the traditional notion that introductions should always be a free exchange based on goodwill, suggesting that the value of one’s network and connections can indeed be recognized through compensation without detracting from the positive intent behind the introduction. Compensated introductions acknowledge the time, effort, and value involved in cultivating high-quality networks. Additionally, by monetizing introductions in a thoughtful and selective way, one can potentially enhance the quality and alignment of the connections made, ensuring that everyone involved sees tangible value. This approach respects the principle of goodwill while recognizing that building and maintaining a valuable network is a skill and asset worth rewarding.
What is the one thing you repeatedly do and recommend everyone else do?
I enjoy taking long walks alone as the walks offer a range of mental, physical, and emotional benefits. Walking alone without distractions allows your mind to process thoughts more clearly. It’s a great way to sort through complex problems, plan out goals, or simply daydream. Long solo walks offer a valuable opportunity to unwind and de-stress. The simple act of moving, combined with fresh air and natural surroundings, has a calming effect on my body and mind. Walks also allow me to sort through feelings, let go of tension, and even experience catharsis, leaving me more grounded and centered. Solitude during a long walk provides me with a rare opportunity for introspection. Away from the noise of everyday life, I can reflect on my goals, relationships, and challenges, gaining valuable insights into my own thoughts and behaviors. Long solo walks provide me with a natural break from screens and technology.
When you feel overwhelmed or unfocused, what do you do?
When I feel overwhelmed, I stop, take a step back, and assess what needs to be done. I write down my tasks, prioritize them, and break larger tasks into smaller, manageable steps. This makes my workload feel more achievable and helps me regain control. Also, tackling one small, high-priority task first helps me build momentum and provide a sense of accomplishment, which motivates me to continue with more focus and clarity. Also, I try to step away, even if it’s just for five minutes. I go for a short walk. Physical movement helps me release built-up tension, clears my mind, and boosts my energy level.
What is one strategy that has helped you grow your business or advance in your career?
I’ve been a serial entrepreneur over the last 30 years. Each time I’ve moved on to my next pursuit, I focused on surrounding myself with hard-working individuals whom I’ve had success with in prior ventures. I believe that a strong, cohesive team is the backbone of any successful endeavour. These are people I know I can trust, both in terms of their work ethic and their integrity. Having worked with them before, I understand their strengths, their weaknesses, and how to bring out their best. This shared history allows us to skip the “getting to know you” phase and dive straight into productive work. Performance expectations are already well established. Moreover, working with individuals who are committed and driven has helped me set a high standard across the team. Their dedication is contagious, creating an environment where everyone feels motivated to put in their best effort. In times of challenge, which are inevitable in any business, I know I can count on them to persevere and stay focused. Ultimately, building a team with proven, like-minded people gives me confidence that we’ll overcome obstacles and achieve our goals together.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
I had built a quite successful business in a highly regulated B2C services industry. We had a new vendor approach us with an offering that purportedly would help us do a better job serving our clients and help support our continued growth. I was very busy juggling a number of other responsibilities in the business so I delegated responsibility for vetting the new vendor to third parties and I was lax in my validation of the vendors adherence to compliance standards. This led to a poor vendor selection, which resulted in catastrophic impacts to the business and to my personal reputation and peace of mind. I. had to step away from the business as a result and my life was turned upside down. I overcame the experience by simply having a never-say-die attitude. Thankfully, my innate ability to persevere in the face of extremely adverse circumstances helped me to power through one of the most difficult circumstances I had ever faced. I made a conscious choice to channel my energy into recovering from the horrific circumstances, rather than feeling victimized by them. The experience reinforced my belief that if one sets their mind to a task and works extremely hard, one can accomplish most things they set out to do, of course to varying degrees. I also learned that one should be very deliberate and careful in identifying the right assistance in selecting the right partners and vendors to support the success of one’s business.
What is one business idea you’re willing to give away to our readers?
I make time to field invitations and call invitations on LinkedIn. While this approach may seem like a time suck, I find that an enormous percentage of those invitations end up turning into opportunities to learn and to generate meaningful relationships. Often, the invitations to connect are for the purpose of soliciting my business, but the calls regularly turn into business opportunities for me. In a sense, those calls are opportunities to “Flip the Sale”. The calls usually start with the other party trying to pitch me on their product or service. Of course, at some point in the conversation, I will start asking about their business. That conversation leads to a discussion of challenges in their business, which then leads to me identifying a business opportunity. Because I had graciously accepted the invitation to connect, human nature dictates that it would be rude of the other party not to accept my assistance in helping them to resolve the challenge in their business. What started as an attempt to sell me a product or service has resulted in me generating a business opportunity.
What is one piece of software that helps you be productive? How do you use it?
Augment.co is an AI agent that gathers an encrypted history of all activities that happen on my computer, including emails, meetings, webpages, documents, etc. It sees everything I see and learns how I talk, what interests me, what meetings I have attended and makes it all searchable. It helps me organize my world all in one closed system. I can search in Augment for a meeting topic or person and find all of the meetings, calendar events, emails, etc between me and that person, as one example of how it makes me productive. I believe Augments goal is to create use case products that can be deployed in various ways, such as a Sales Augment to assist organize and assist a sales person so everything related to a sales opportunity can be gathered in one place. It’s kind of like having an awesome virtual assistant (who’s also a stenographer) sitting on your shoulder at all times and keeping you organized.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
I’m not a huge consumer of podcasts or books, although I highly recommend Who by Geoff Smart and Randy Street. The book provides a comprehensive guide for business owners and leaders on how to make better hiring decisions. The book offers a step-by-step approach to identifying, recruiting, and selecting the right talent for your business by using the “A Method.” This method helps you define clear outcomes for the role, systematically evaluate candidates, and make informed hiring decisions based on data rather than gut feeling. The book’s value lies in its potential to reduce costly hiring mistakes and enhance the quality of your team. The book emphasizes that a company’s success is built on the strength of its people, and it presents practical, actionable advice on how to attract top talent who align with your company’s goals and culture. By using the techniques in Who, you can streamline your hiring process, increase productivity, and ultimately build a stronger, more capable organization.
Another great book I have read is From Good to Great: Why Some Companies Make the Leap… and Others Don’t by Jim Collins. The book that explores why certain companies manage to transition from being merely good to truly exceptional, while others remain average. Collins and his research team studied businesses that made and sustained significant improvements in their performance over time, identifying key factors that contributed to their success. The book introduces concepts like the Hedgehog Concept (focusing on what a company can be the best at), Level 5 Leadership (leaders who blend humility with determination), and the Flywheel Effect (the momentum that builds from sustained effort in the right direction). As a business owner, you’ll find immense value in From Good to Great because it breaks down the essential elements that drive sustained, high-level success. Collins’ insights can help you focus on your company’s unique strengths, cultivate the right leadership qualities, and create a strategic vision that drives long-term growth. This book provides actionable principles for transforming your business from a solid performer into an industry leader.
Of course, I learn the most by hosting Sanguine’s Mindshare Webinar Series: Empowering Businesses Through Insightful Discussions. The webcast series provides a platform for thought-provoking discussions on a wide range of business-related topics. The Mindshare series is designed to offer valuable insights, practical advice, and industry-leading expertise to help entrepreneurs, executives, and business leaders navigate the ever-evolving landscape of the modern business world. The primary goal of the Mindshare series is to create a collaborative and informative environment where business professionals can come together to learn, share, and grow. We firmly believe that the exchange of ideas and the sharing of experiences are essential for driving innovation, overcoming challenges, and achieving sustainable success.
By hosting these webinars, we aim to:
1. Provide Actionable Insights: Each Mindshare session features subject matter experts who dive deep into specific business topics, offering attendees practical strategies, tools, and best practices that they can immediately apply to their own organizations.
2. Foster Networking and Collaboration: The interactive nature of the Mindshare webinars encourages participants to engage with one another, share their own experiences, and explore potential synergies and partnerships.
3. Stay Ahead of Industry Trends: The Mindshare series covers a diverse range of business-related topics, from emerging technologies and marketing strategies to compliance and legal considerations. This allows our attendees to stay informed and ahead of the curve in their respective industries.
The Mindshare webinar series covers a wide variety of business-related topics, catering to the diverse needs and interests of our audience. Some of the key areas we’ve explored in the past include:
• Digital Transformation: Discussions on the latest advancements in technology and their impact on business operations, customer experiences, and competitive advantages.
• Marketing and Lead Generation: Strategies for leveraging digital marketing, social media, and innovative lead generation tactics to drive business growth.
• Compliance and Legal Considerations: Insights into navigating the ever-changing regulatory landscape, ensuring data privacy, and mitigating legal risks.
• Operational Efficiency: Best practices for streamlining workflows, automating processes, and optimizing resource allocation to enhance productivity and profitability.
• Entrepreneurial Mindset: Discussions on the key traits, strategies, and challenges faced by successful entrepreneurs and business leaders.
By covering such a diverse range of topics, the Mindshare series provides attendees with a well-rounded understanding of the critical factors that contribute to business success in the modern era.
What’s a movie or series you recently enjoyed and why?
I recently saw Dune, Part Two and liked it even better than the first movie, which was also pretty amazing. The movie is a visually stunning and narratively powerful continuation of the first movie. From a story standpoint, it excels by deepening the characters’ journeys, particularly Paul Atreides as he grapples with destiny, power, and his role in the fate of Arrakis. The film balances action with thoughtful exploration of complex themes like political intrigue, environmental stewardship, and the clash of cultures. Aesthetically, Dune: Part Two is mesmerizing. The cinematography is breath-taking, capturing the harsh yet beautiful landscapes of Arrakis in sweeping shots that highlight the scale and desolation of the desert. The set designs, costumes, and special effects are meticulously crafted, creating an immersive, tactile experience that feels grounded and grandiose. The soundtrack heightens the film’s emotional depth and intensity. Together, these elements make Dune: Part Two not only a compelling story but also a work of art that pushes the boundaries of sci-fi cinema. I’m not a huge sci-fi guy, but this movie was impressive.
Key learnings
- Engage Directly with Clients and stakeholders: Make your day more productive by actively engaging with clients or stakeholders to understand their challenges and deliver solutions that truly make a difference.
- Develop Ideas through Small Steps: Bring ideas to life by taking a series of small, exploratory steps to validate and refine them before committing significant time and resources.
- Stay Curious about Emerging Technologies: Embrace advancements in artificial intelligence and other transformative technologies to stay ahead in your industry and find innovative ways to improve your business.
- Prioritize Work-Life Balance: Schedule dedicated personal time during your day to focus on important tasks, exercise, or unwind. This balance will boost your productivity and overall well-being.
- Monetize Your Network Thoughtfully: Consider compensated introductions within your network to recognize the value of your connections while ensuring alignment and quality in the connections you make.