Podcasts about business lunch

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Best podcasts about business lunch

Latest podcast episodes about business lunch

Business Lunch
Intelligent Data: Empowering Ai Development With Lucy Guo

Business Lunch

Play Episode Listen Later Aug 29, 2025 38:38


In this episode of the Business Lunch podcast, host Roland Frasier sits down with Lucy Guo, a remarkable entrepreneur who made her mark in a short amount of time. Lucy takes us through her inspiring journey, starting from her early days as a kindergartener selling Pokemon cards and colored pencils to her groundbreaking roles as an intern at Facebook and the first female designer at Snap.Lucy's shares how she leveraged platforms like PayPal and eBay to turn her skills into financial opportunities. Lucy and Roland delve into the topic of coding and its importance in today's landscape. While Lucy acknowledges the rise of no-code tools, she emphasizes the value of understanding coding fundamentals, particularly when it comes to managing engineering teams and making informed decisions about app development.This podcast episode offers a captivating glimpse into Lucy Guo's entrepreneurial journey, filled with valuable insights and lessons for aspiring entrepreneurs.HIGHLIGHTS"I was always an entrepreneur growing up... I was selling Pokemon cards and colored pencils for money." "Knowing how to code is important... the best sites today and the best apps today, you still need a team of engineers."“If you are just a business person and you are hiring a team of engineers, you're gonna get ripped off."Mentioned in this episode:Get Roland's Training on Acquiring Businesses!Discover The EXACT Strategy Roland Has Used To Found, Acquire, Scale And Sell Over Two Dozen Businesses With Sales Ranging From $3 Million To Just Under $4 Billion! EPIC Training

Wintrust Business Lunch
Wintrust Business Lunch 8/27/25 – Terry Savage: All eyes are on the Fed

Wintrust Business Lunch

Play Episode Listen Later Aug 27, 2025


Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about why she believes the Fed will likely be cutting rates in September, what would happen if the Fed does cut rates, how interest rates actually work, and the benefits and pitfalls of AI. And as always, Terry answers all of your financial questions.

Wintrust Business Lunch
Wintrust Business Lunch 8/26/25: Strong consumer confidence, market health, Lisa Cook removal

Wintrust Business Lunch

Play Episode Listen Later Aug 26, 2025


Faron Daugs, CFP, Founder and CEO, Harrison Wallace Financial Group, joins John to talk about the market not having much of a reaction to President Trump trying to fire Federal Reserve Board member Lisa Cook, the overall health of the economy, the impact of tariffs still being relatively unknown, consumer confidence coming in stronger than expected, and the […]

Wintrust Business Lunch
Wintrust Business Lunch 8/25/25: Intel stake, Fed rate cut looming, AI curriculum, youth hockey boom

Wintrust Business Lunch

Play Episode Listen Later Aug 25, 2025


Segment 1: Ilyce Glink, owner of Think Glink Media, joins John Williams to talk about if August is a good time to put a house on the market, current mortgage rates, why the government took a 10% stake in Intel, when the Fed is likely to cut interest rates, and how the market typically performs after the Fed cuts […]

Wintrust Business Lunch
Wintrust Business Lunch 8/22/25: Big market rally, Fed interest rate pivot, Public Works Expo

Wintrust Business Lunch

Play Episode Listen Later Aug 22, 2025


Segment 1: Craig Bolanos, Founder and Wealth Advisor at VestGen Wealth Partners, joins John to talk about today’s big market rally after Fed Chairman Jerome Powell suggested interest rate cuts would be coming soon, how many rate cuts he expects to see for the rest of 2025, and when we we’ll see the full impact of tariffs. […]

Wintrust Business Lunch
Wintrust Business Lunch 8/21/25: Market pullback, Fed waiting, AI scams

Wintrust Business Lunch

Play Episode Listen Later Aug 21, 2025


Segment 1: Steven Esposito, President of Yellowstone Wealth Management in Lake Forest, joins John to talk about why the markets have been down recently, the odds of a Fed interest rate cut, how many rate cuts he can expect this year, and why this may be a good buying opportunity. Segment 2: Jason Hiner, Editor in Chief, ZDNET, joins John […]

Business Lunch
From Cash Crunch to Cash Flow: Expense Optimization Tactics

Business Lunch

Play Episode Listen Later Aug 20, 2025 40:15


Welcome to a new episode of Business Lunch! Today, hosts Roland Frasier and Richard Lindner dive deep into a practical framework for optimizing business expenses—perfect for founders, business owners, and financial leaders. Whether you're facing a cash flow crunch or simply want to boost your bottom line, this episode is packed with actionable strategies to help you identify, analyze, and cut unnecessary costs while maintaining business momentum.Highlights:"Every extra million dollars helps, every extra $100,000 a month helps.""Profit dies by a thousand cuts, especially with forgotten subscriptions.""Don't wait for things to get bad to make things better.""If you're operating on a 25% profit margin, cutting $100,000 is like adding $400,000 in sales."Timestamps:00:00 – The Payment Terms Dilemma: Cash Flow vs. Sales Velocity01:32 – Why Every Business Needs a Bottom Line Review03:10 – Testing 12-Month Payment Terms: Results & Risks06:24 – The Impact of GAAP Accounting on Revenue Recognition08:40 – The STOP Framework: Where to Start Cutting13:24 – Evaluating Team ROI: Scorecards & Underperformance15:39 – Tools & Tech: The Hidden Cost of Subscriptions18:59 – Operations & Overhead: Renegotiating Leases and Utilities26:46 – The SAVE Process: Scan, Analyze, Verify, Execute34:56 – Why Quarterly Expense Reviews MatterCONNECT • Ask Roland a question HERE.RESOURCES:• 7 Steps to Scalable workbook • Get my book, Zero Down, FREETo learn more about Roland Frasier

Business Lunch
The CEO Shift: The Changing Roles in Business

Business Lunch

Play Episode Listen Later Aug 20, 2025 37:48


Join us as we delve into the dynamic world of executive leadership and pivotal moments of transition in this engaging episode of the Business Lunch podcast. Hosts Roland Frasier and Ryan Diess kick off with a lively banter, setting the stage for a deep dive into the complexities of being a CEO. The episode features a detailed discussion on the stepping down of Bumble's CEO, exploring the nuanced reasons behind such significant career decisions.Throughout the conversation, Ryan and Roland offer insights into the multifaceted nature of executive roles, particularly focusing on the differences and responsibilities of CEOs and COOs. They bring their own experiences into the discussion, providing listeners with real-world examples and practical advice.This episode is a treasure trove for anyone interested in the intricacies of business leadership, whether you're an aspiring entrepreneur, a seasoned executive, or simply curious about the dynamics of high-level management.It's an insightful journey into what it means to lead, adapt, and grow in today's fast-paced business environment.Highlights:"I think that the most important thing is to be able to have a conversation with somebody and to be able to disagree with them and still respect them."“I want to know all the people I'm working with by name and you know, see how they're doing and know about their families and do barbecue.”“No one can run your business like you do.Highlights: "I think that the most important thing is to be able to have a conversation with somebody and to be able to disagree with them and still respect them."“I want to know all the people I'm working with by name and you know, see how they're doing and know about their families..."“No one can run your business like you do.”Timestamps: (0:00:00) - Considering Leadership Transitions(0:14:17) - Consider Hiring CEO or COO(0:23:07) - CEO vs COO and Hiring Specialists(0:33:02) - Acquiring Successful Businesses Is More EffectiveCONNECT • Ask Roland a question HERE.RESOURCES: • 7 Steps to Scalable workbook • Get my book, Zero Down, FREETo learn more about Roland Frasier

Wintrust Business Lunch
Wintrust Business Lunch 8/20/25 – Terry Savage answers your financial questions

Wintrust Business Lunch

Play Episode Listen Later Aug 20, 2025


Nationally syndicated financial columnist and author Terry Savage joins John Williams to answer all of your financial questions.

Wintrust Business Lunch
Wintrust Business Lunch 8/19/25: Job mobility, merger risks, Lower Tech Bills

Wintrust Business Lunch

Play Episode Listen Later Aug 19, 2025


Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins John to talk about a recent Wall Street Journal article that breaks down why America’s mobility is stalling. Segment 2: Philippe Weiss, President, Seyfarth at Work, joins John to talk about the surge in mergers and acquisitions activity and what companies and employees should be aware of […]

Wintrust Business Lunch
Wintrust Business Lunch 8/18/25: Job hugging, home values, Uber Freight shakeup, Chicago Slice Paddle in the Park

Wintrust Business Lunch

Play Episode Listen Later Aug 18, 2025


Segment 1: Ilyce Glink, owner of Think Glink Media, joins John Williams to talk about the trend of ‘job hugging’ and how workers are clinging to their jobs, where home values are rising and falling. Segment 2: Jim Dallke, Director of Communications, TechNexus Venture Collaborative, tells John about a Chicago startup that helps social service agencies book hotels for people in need being […]

Wintrust Business Lunch
Wintrust Business Lunch 8/15/25: Tariff impact on prices, BLS data, small business survey, Social Security anniversary

Wintrust Business Lunch

Play Episode Listen Later Aug 15, 2025


Segment 1: Michael Miller, Economics Professor, Western Washington University and Professor Emeritus at DePaul University, joins John Williams to talk about how tariffs will impact general prices, why markets are still hitting all-time highs, when the Fed might cut interest rates, and to explain why initial labor report numbers are typically not reliable. Segment 2: Mike Spriggs, […]

Wintrust Business Lunch
Wintrust Business Lunch 8/14/25: Hot inflation, Fed rate decision, ChatGPT update

Wintrust Business Lunch

Play Episode Listen Later Aug 14, 2025


Segment 1: Jason Turner, Chief Investment Strategist for Wintrust Wealth Management, joins John to talk about why the stock market continues to rise despite economic uncertainty, his thoughts on today’s hot inflation report, and if he thinks the Fed might cut rates in September. Segment 2: Jason Hiner, Editor in Chief, ZDNET, joins John to talk […]

Wintrust Business Lunch
Wintrust Business Lunch 8/13/25 – Terry Savage: Stock market hitting new records

Wintrust Business Lunch

Play Episode Listen Later Aug 13, 2025


Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about the market hitting all-time highs and what to know if you are planning for retirement. Terry also answers all of your financial questions.

Wintrust Business Lunch
Wintrust Business Lunch 8/12/25: Job relocation, work friendships, new home sales flat

Wintrust Business Lunch

Play Episode Listen Later Aug 12, 2025


Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins John to talk about the job market tightening and the sacrifices that might need to be made to land a job. Tom also talks about the importance of making friends at work. Segment 2: Dennis Rodkin, residential real estate reporter for Crain's, joins John to talk about new home […]

Wintrust Business Lunch
Wintrust Business Lunch 8/11/25: Buy Now, Pay Later, AI regulations, Leona's 75th anniversary

Wintrust Business Lunch

Play Episode Listen Later Aug 11, 2025


Segment 1: Ilyce Glink, owner of Think Glink Media, joins John Williams to talk about how many people are using ‘Buy Now, Pay Later’ services, Nvidia and AMD agreeing to pay 15% of revenues from chip sales to China to the U.S. government, and how AI is creating billionaires. Segment 2: Jim Dallke, Director of Communications, TechNexus Venture Collaborative, tells John about […]

Business Lunch
The Lean Team Dilemma: AI, Efficiency & Business Value

Business Lunch

Play Episode Listen Later Aug 8, 2025 35:13


Welcome to a new episode of Business Lunch! In this episode, Roland Frasier and Richard Lindner take a look at the current trend of running businesses with ultra-lean teams, the role of AI in operational efficiency, and the real impact these choices have on business value and potential for acquisition. Whether you're a founder, operator, or executive looking to optimize your team, scale profitably, or prepare your business for sale, this episode is packed with insights on balancing technology, human capital, and long-term growth.Highlights:"It's a badge of honor to operate with as few people as possible.""If you're a lifestyle business, build a lifestyle business. If you're building to sell, you're selling the ability to execute.""Trying to be lean in customer support is usually to give poor customer support.""Small businesses that are overly lean are just not going to be as marketable as companies that have redundancies."Timestamps:00:00 – Introduction01:05 – The Lean Team Trend: Entrepreneurs and the new badge of honor02:44 – Three Business Models: Lifestyle, lean tech, and scalable teams05:49 – Technology as Amplifier: Roles for tech and humans08:13 – The Customer Support Cautionary Tale: $40M savings gone wrong12:16 – Human Touch in Customer Service: Why empathy matters15:45 – Transferable Value: The importance of cross-training and redundancy19:28 – Critical Roles for Lean, Profitable Companies: Finance, marketing, sales, and tech24:26 – Departmental Tech Specialists: Bridging humans and AI30:16 – Digital Marketer's AI Solutions: How to get started and who it's forCONNECT • Ask Roland a question HERE.RESOURCES:• 7 Steps to Scalable workbook • Get my book, Zero Down, FREETo learn more about Roland Frasier

Wintrust Business Lunch
Wintrust Business Lunch 8/8/25: Market gains, trade deals, rising auto prices

Wintrust Business Lunch

Play Episode Listen Later Aug 8, 2025


Segment 1: Craig Bolanos, Founder and Wealth Advisor at VestGen Wealth Partners, joins Jon Hansen, filling in for John Williams, to talk about the overall health of the markets and the economy, how market volatility has almost collapsed, why it’s a good time to rebalance your portfolio, Trump nominating CEA chair Stephen Miran to the Federal Reserve […]

Wintrust Business Lunch
Wintrust Business Lunch 8/7/25: Mini-retirement, Abt back-to-school tech, Taste of Elmwood Park

Wintrust Business Lunch

Play Episode Listen Later Aug 7, 2025


Segment 1: Elmwood Park Village President Angelo “Skip” Saviano tells John everything you need to know about the 2025 Taste of Elmwood Park! Segment 2: Business Journalist Mallika Mitra joins Jon Hansen to share the story behind her article, “The Case for Taking Mini-Retirements Along the Way in Your Career.” Mitra explains why more professionals, especially […]

Wintrust Business Lunch
Wintrust Business Lunch 8/6/25 – Terry Savage: Is an economic slowdown coming?

Wintrust Business Lunch

Play Episode Listen Later Aug 6, 2025


Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about the vibe shift happening surrounding the strength of the economy, the uncertainty over tariffs and how they will impact consumers, the softening of the job market, the latest on student loans, and what to know about interest rates and T Bills. Terry also answers […]

Business Lunch
Merging Old-School with AI: Strategies for Success

Business Lunch

Play Episode Listen Later Aug 5, 2025 27:45


Welcome to a new episode of Business Lunch! In this episode, Roland Frasier and Ryan Deiss dive into the emerging trend of rolling up traditional businesses and supercharging them with AI. They discuss the opportunities and pitfalls of this strategy, offer advice for old-school business owners, aspiring platform companies, and investors, and share real-world examples of value creation through AI integration. This episode is perfect for entrepreneurs, business owners considering acquisitions, and anyone curious about the intersection of AI and business growth.Highlights:"Roll ups fail at the integration level, and the integration is really what systems do we have to do that?""If you don't invest in up-leveling and AI-fying your business now, you'll be acquired on the cheap.""The basic building blocks of why you would do a roll up, applied with AI and tech, make perfect sense to me.""If you're planning on just shutting it down or letting it die a slow and profitable death, then cool. But if it's longer than that, you either have to get on the bus or face being put out of business."Timestamps:00:00 Introduction04:15 AI and Roll-Ups: Success and Failure 07:16 Advice for Old-School Businesses 10:30 Investor Strategy and Execution 16:05 Management and Systems for Roll-Ups 17:56 Investor Strategy: Mergers and Acquisitions 20:52 Value Addition through AI CONNECT • Ask Roland a question HERE.RESOURCES:• 7 Steps to Scalable workbook • Get my book, Zero Down, FREETo learn more about Roland Frasier

Wintrust Business Lunch
Wintrust Business Lunch 8/5/25: Work ethic, celebratory layoffs, TJ Stearns Financial Planning and Benefits

Wintrust Business Lunch

Play Episode Listen Later Aug 5, 2025


Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins Jon Hansen, filling in for John Williams, to talk about how some workers today are more concerned about individual wants rather than what is necessary to achieve. Tom says sometimes you just need to put your head down and work and success will come. Segment […]

Wintrust Business Lunch
Wintrust Business Lunch 8/4/25: Jobs report revisions, rising prices, work flexibility, Canal Street Eatery

Wintrust Business Lunch

Play Episode Listen Later Aug 4, 2025


Segment 1: Ilyce Glink, owner of Think Glink Media, joins Jon Hansen to talk about Fridays job report, revisions, the importance of getting real data, President Trump firing Bureau of Labor Statistics Commissioner Erika McEntarfer, if she believes prices are going to rise, and what you should know about the recently passed “trigger leads” law. Segment 2: Jim Dallke, Director […]

Business Lunch
AI, Disruption, Sales, and the Path to Success as a Small Business

Business Lunch

Play Episode Listen Later Aug 1, 2025 38:29


Welcome to a new episode of Business Lunch! In this episode, Roland Frasier and Ryan Deiss dive into the real challenges facing small and medium-sized businesses today, cutting through the marketing spin of industry reports. If you're a business owner, entrepreneur, marketer, or anyone interested in practical strategies for growth, customer acquisition, and leveraging AI, this episode is for you. Tune in for candid insights, actionable advice, and a few laughs along the way.Highlights:“I've never once in my entire life heard a small business owner use the word ‘resilience.'”“If your offer is confusing, it's not going to work, simplicity wins right now.”“AI is the single biggest disruptive event any of us have ever experienced.”“Let people buy the way they want to buy.”Timestamps:00:00 - Introduction01:36 – Salesforce Report: Hype or Help?03:57 – Do Business Owners Really Say ‘Resilience'?05:14 – AI Adoption: Fear of Losing the Human Touch07:38 – What Are the Real Top Challenges?11:07 – How Macroeconomics Impact Sales15:23 – Simplifying Offers for Better Results17:41 – Creating a ‘Happening' to Re-Engage Customers21:05 – AI-ifying Your Business: Pivot or Perish28:04 – Acquisitions: The Private Equity Playbook for SMBsCONNECT • Ask Roland a question HERE.RESOURCES:• 7 Steps to Scalable workbook • Get my book, Zero Down, FREETo learn more about Roland Frasier

Wintrust Business Lunch
Wintrust Business Lunch 8/1/25: Weak job market, Fed future, Back-to-School survey

Wintrust Business Lunch

Play Episode Listen Later Aug 1, 2025


Segment 1: Jane Oates, Senior Policy Advisor and recent President at WorkingNation, joins John Williams to breakdown the July labor report, why the monthly revisions were so concerning, and if the numbers will put more pressure on the Fed to cut rates. Segment 2: Matt Adams, principal at Deloitte Consulting specializing in retail, gives John all the details […]

Wintrust Business Lunch
Wintrust Business Lunch 7/30/25 – Terry Savage: Why the Fed is holding rates steady

Wintrust Business Lunch

Play Episode Listen Later Jul 30, 2025


Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about Mayor Johnson’s efforts to tax the ultra-rich, the economic data released today including a strong GDP report, why the housing market is a cause for concern, the dilemma the Fed is facing about cutting rates, and what she expects from Friday’s labor report. Terry […]

Wintrust Business Lunch
Wintrust Business Lunch 7/29/25: Intern benefits, team building, Fed decision looms

Wintrust Business Lunch

Play Episode Listen Later Jul 29, 2025


Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins John to talk about the death of Cubs Hall of Famer Ryne Sandberg, how great chemistry is key to building a good team, the value of an internship and getting your foot in the door, and the importance of building bonds with your co-workers. Segment […]

Wintrust Business Lunch
Wintrust Business Lunch 7/28/25: Trade deals, Fed outlook, quantum computing, Cradles to Crayons

Wintrust Business Lunch

Play Episode Listen Later Jul 28, 2025


Segment 1: Phillip Shaw, CFP, Senior Advisor, Goldstone Financial Group, joins John to talk about the markets being impervious to economic uncertainty, if it’s too early to assess the impact of tariffs, where he’s telling clients to park their money, what he expects from the Fed meeting this week, when the Fed should start cutting interest […]

Business Lunch
The Great Flattening: How AI Is Reshaping Teams and Management

Business Lunch

Play Episode Listen Later Jul 26, 2025 63:16


Welcome to a new episode of Business Lunch!In this episode, Roland Frasier and Ryan Deiss dive into "the great flattening"—the radical shift where AI enables entire departments, and even companies, to be run by a single person. They explore real-world examples from tech and traditional industries, discuss the risks and rewards of this new model, and offer practical advice for leaders and entrepreneurs. If you're a business owner, manager, or anyone interested in the future of work, this episode is for you!Highlights:"What if the highest performing marketing team at your company was actually just one person?""AI is compressing entire departments into individual 'departments of one.'""The coordination tax is the overhead of meetings, getting along, and not getting along.""This may be the end of the middle manager and the rise of the player-coach."Timestamps:01:41 – Introducing "The Great Flattening" Concept02:30 – WhatsApp: $345M Value Per Employee03:30 – Midjourney & Cursor: Creative and Dev Pancakes07:21 – The Coordination Tax Explained11:18 – Team Size, Efficiency, and the Two Pizza Rule14:25 – AI Agents Replacing Marketing Teams22:35 – Risks of Single-Person Departments26:53 – The End of Middle Management?37:19 – The Pancake Test: Is Your Department "Pancakeable"?54:20 – Digital Marketer's Department of One Beta ProgramCONNECT • Ask Roland a question HERE.RESOURCES:• 7 Steps to Scalable workbook • Get my book, Zero Down, FREETo learn more about Roland Frasier

Wintrust Business Lunch
Wintrust Business Lunch 7/25/25: Market rally, interest rate outlook, South Chicago Packing, Loop activity

Wintrust Business Lunch

Play Episode Listen Later Jul 25, 2025


Segment 1: Steven Esposito, President of Yellowstone Wealth Management in Lake Forest, talks to John about today’s market rally, the Trump v. Jerome Powell feud, why he thinks interest rates should be lower, why Powell might be hesitant to lower rates, his thoughts on the trade deals and what that could mean for the market, the rotation into the […]

Wintrust Business Lunch
Wintrust Business Lunch 7/24/25: Job survey, AI action plan, data center water crisis, Chicago Pizza Pass

Wintrust Business Lunch

Play Episode Listen Later Jul 24, 2025


Segment 1: Mark Hamrick, Washington Bureau Chief and Senior Economic Analyst for Bankrate.com, talks to John about a new Bankrate survey that shows nearly 1 in 2 workers plan to search for a new job in the coming year. Segment 2: Bree Fowler, Senior Writer, CNET, joins John Williams to talk about President Donald Trump unveiling a new plan for […]

Wintrust Business Lunch
Wintrust Business Lunch 7/23/25 – Terry Savage: Evaluate your asset allocation

Wintrust Business Lunch

Play Episode Listen Later Jul 23, 2025


Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about how how the market has performed since President Trump’s tariff announcement, what that market swing means for your 401(k), why it’s a good time to revisit your asset allocation, and what it means that 401(k) plans have caught the eye of Wall Street insiders. […]

Business Lunch
Navigating Economic Slowdowns: Strategies for Summer Success

Business Lunch

Play Episode Listen Later Jul 22, 2025 35:19


Welcome to a new episode of Business Lunch. Today, we discuss practical strategies to navigate economic slowdowns, particularly during summer. They share insights on creative marketing, leveraging internal resources, and maximizing downtime. Whether you're experiencing a seasonal dip or a broader economic challenge, this episode is packed with actionable advice to keep your business thriving.Highlights:"The quickest way to drown out negativity is with an abundance of positivity.""The Lord puts you into these situations knowing you can handle them. It's a test.""Hard makes you resilient. Soft and easy doesn't make you resilient."Timestamps:00:00 - Introduction02:30 - Current Economic Trends05:00 - Seasonal Slowdowns10:00 - Strategies to Combat Slowdowns15:00 - Leveraging Internal Resources20:00 - Creative Marketing Ideas25:00 - The Importance of Not Panicking30:00 - Enhancing Offers and Bundles35:00 - Acquisition Opportunities40:00 - Long-Term Planning and TestingCONNECT • Ask Roland a question HERE.RESOURCES:• 7 Steps to Scalable workbook • Get my book, Zero Down, FREETo learn more about Roland Frasier

Grow A Small Business Podcast
How Kerry Boulton of Exit Strategy Group Tripled a Freight Biz to $50M with 63 Staff, Now Guides Owners to Be ‘Exit Ready' & Spot Their Alan Bond Moment — Secrets on Cash, People & Freedom from 38 Yrs in Business. (Episode 699 - Kerry Boulton

Grow A Small Business Podcast

Play Episode Listen Later Jul 22, 2025 64:30


In this episode of Grow a Small Business host Troy Trewin interviews Kerry Boulton from Exit Strategy Group, who shares her incredible journey of buying a freight business doing $16M and growing it to $50M with the same 63 staff. Kerry reveals how she executed a strategic exit after seven years, then went on to build and sell multiple ventures. Now through The Exit Strategy Group, she mentors owners on being “always exit ready,” balancing business, financial, and personal goals. She discusses the power of systems, the Value Builder tool, and finding your “Alan Bond moment.” Kerry's story is a masterclass in scaling, cash flow, people, and creating true freedom. Other Resources: An easy way to measure if your customers love you in 21 minutes – use the Net Promoter Score (NPS). And it's FREE. Maximise Your Business Sale Price To Meet Your Expectations! How to Exit Your Business Feeling Fulfilled Personally Satisfied and Have the Biggest Pay Day of Your Life Why would you wait any longer to start living the lifestyle you signed up for? Balance your health, wealth, relationships and business growth. And focus your time and energy and make the most of this year. Let's get into it by clicking here. Troy delves into our guest's startup journey, their perception of success, industry reconsideration, and the pivotal stress point during business expansion. They discuss the joys of small business growth, vital entrepreneurial habits, and strategies for team building, encompassing wins, blunders, and invaluable advice. And a snapshot of the final five Grow A Small Business Questions: What do you think is the hardest thing in growing a small business? According to Kerry Boulton, the hardest thing in growing a small business is managing cash flow. Growth eats up cash faster than most owners expect, and many don't realize how easily they can run into a squeeze. She says you've got to keep a constant eye on cash, plan ahead, and understand that scaling up often means funding gaps you need to prepare for. What's your favorite business book that has helped you the most? Kerry shares that her favorite business book is “The Seven Habits of Highly Effective People” by Stephen Covey, which she says gave her a rock-solid foundation for both business and life. She also loves “The Great Game of Business” by Jack Stack for teaching how to build financial literacy and an ownership mindset in your team. Are there any great podcasts or online learning resources you'd recommend to help grow a small business? For podcasts and learning resources, Kerry highly recommends “Built to Sell Radio” by John Warrillow, which dives into making your business more valuable and sellable. She also likes “Business Lunch” with Roland Frasier & Ryan Deiss, plus the Exit Planning Institute's podcast. And of course, she's a fan of Troy's Grow Small Business Podcast, which she appeared on. What tool or resource would you recommend to grow a small business? When it comes to tools, Kerry swears by the Value Builder System, which helps owners see their business through a buyer's eyes, score it across key value drivers, and figure out exactly where to improve to maximize value and exit readiness. What advice would you give yourself on day one of starting out in business? If she could give herself advice on day one of starting out in business, Kerry laughs and says she'd simply tell herself to “buckle up,” because it's going to be a hell of a ride—full of challenges, personal growth, and ultimately the chance to create freedom and live life on her own terms. Book a 20-minute Growth Chat with Troy Trewin to see if you qualify for our upcoming course. Don't miss out on this opportunity to take your small business to new heights! Enjoyed the podcast? Please leave a review on iTunes or your preferred platform. Your feedback helps more small business owners discover our podcast and embark on their business growth journey.     Quotable quotes from our special Grow A Small Business podcast guest: Always run your business as if you'll sell it tomorrow — that's how you build something truly valuable — Kerry Boulton Buckle up — because business is the best roller coaster ride you'll ever take — Kerry Boulton Cash is the oxygen of your business; ignore it and you'll suffocate — Kerry Boulton      

Wintrust Business Lunch
Wintrust Business Lunch 7/22/25: Trump-Powell feud, office romance, work efficiency

Wintrust Business Lunch

Play Episode Listen Later Jul 22, 2025


Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins John to talk about the Coldplay ‘Kiss Cam’ couple and how to handle these situations when they show up in the workplace. Segment 2: Philippe Weiss, President, Seyfarth at Work, joins John to talk about the peril that often comes with more power. In a quest for […]

Wintrust Business Lunch
Wintrust Business Lunch 7/21/25: Home inventory, TechChicago Week, Venetian Night

Wintrust Business Lunch

Play Episode Listen Later Jul 21, 2025


Segment 1: Ilyce Glink, owner of Think Glink Media and Best Money Moves, joins John Williams to talk about home inventory hitting a 5-year high, and the latest ping pong game of ‘he said-he said’ between President Trump and Treasury Secretary Scott Bessent. Segment 2: Jim Dallke, Director of Communications, TechNexus Venture Collaborative, tells John about the big events happening for TechChicago […]

Wintrust Business Lunch
Wintrust Business Lunch 7/18/25: Market round-up, small business success, June's Fiserv Small Business Index and The LaSalle Chicago Hotel

Wintrust Business Lunch

Play Episode Listen Later Jul 18, 2025


Segment 1: Ilyce Glink, owner of Think Glink Media and Best Money Moves, joins John Williams to ‘color in’ the details surrounding what the markets have done this past week. Segment 2: Dave Charest, Director of Small Business Success for Constant Contact joins John Williams to talk about how small businesses stay on top during summer, the slow season. Dave […]

Wintrust Business Lunch
Wintrust Business Lunch 7/17/25: Credit cards, Mark Zuckerberg and Meta lawsuit, candle to help Texas relief

Wintrust Business Lunch

Play Episode Listen Later Jul 17, 2025


Segment 1: Ted Rossman, Senior Industry Analyst at Bankrate, joins John to share tips on how to pay off credit card debt. Segment 2: Bree Fowler, Senior Writer, CNET, cnet.com, joins John to talk about the class action $8 billion investors' lawsuit against Meta CEO Mark Zuckerberg and the company leaders, and other business news. […]

Wintrust Business Lunch
Wintrust Business Lunch 7/14/25: Tariffs, iAsk.ai and Lighting Environments

Wintrust Business Lunch

Play Episode Listen Later Jul 15, 2025


Segment 1: Paul Nolte, Senior Wealth Advisor and Market Strategist, Murphy & Sylvest, joins John to talk about the ongoing news surrounding tariffs. Then, Paul breaks down bank earnings and inflation data. Segment 2: Brad Folkens, Co-founder, iAsk.ai joins John to talk about what makes this software so useful for all A.I. curious users. Segment 3: Erin […]

Wintrust Business Lunch
Wintrust Business Lunch 7/15/25: CPS layoffs, the pros and cons of the CTA and Consumer prices rose 0.3% last month

Wintrust Business Lunch

Play Episode Listen Later Jul 15, 2025


Segment 1: Tom Gimbel, job expert and founder of LaSalle Network, joins John to talk about CPS layoffs and what types of jobs those people try and get post-layoffs. Tom then pivots and discusses the importance of the CTA as well as the problems with it and how those aspects impact Chicago businesses and commuters. Segment 2: Craig […]

Business Lunch
The Power of Taking Time Off: Why Entrepreneurs Need to Unplug

Business Lunch

Play Episode Listen Later Jul 11, 2025 27:54


Welcome to a new episode of Business Lunch! In this episode, Roland Frasier and Ryan Deiss dive deep into the importance of taking real vacations as entrepreneurs and business owners. They share personal stories about extended time off, discuss the dangers of burnout, and offer practical advice on setting boundaries and making rest a non-negotiable part of your business life. The conversation covers how stepping away can reset your habits, boost creativity, and ultimately make you more productive and fulfilled. This episode is a must for entrepreneurs, business owners, solopreneurs, and anyone feeling overwhelmed by their work. If you struggle to take time off, feel burned out, or want to learn how rest can actually help your business thrive, this conversation is for you.Highlights:“You have to not let your work schedule bully you.”“Burnout happens when you run out of options and get super hyper resentful of the business.”“Rest is work. You actually are more productive when you take some time off.”“If you're in a state of extreme burnout, before you do something drastic, take at least one week off.”Timestamps:00:00 - Returning from Vacation: Setting the Stage00:38 - The Value of a 30-Day Break00:54 - Off-Peak Living and Family Scheduling03:55 - Work Expands to Fill Your Time07:18 - There's Never a Perfect Time for Vacation0:09:22 - Burnout and Resentment: The Real Cost0:10:54 - Teams vs. Solopreneurs: The Vacation Impact14:11 - Why Your Business Exists to Serve You19:18 - Staycations and Non-Negotiable Time Off21:58 - Advice for Burnout: Take a Break Before QuittingCONNECT • Ask Roland a question HERE.RESOURCES:• 7 Steps to Scalable workbook • Get my book, Zero Down, FREETo learn more about Roland Frasier

Wintrust Business Lunch
Wintrust Business Lunch 7/11/25: Tariff power, immigrant economic impact, Candl birthday app

Wintrust Business Lunch

Play Episode Listen Later Jul 11, 2025


Segment 1: Michael Miller, Economics Professor, Western Washington University and Professor Emeritus at DePaul University, joins John Williams to talk explain how one person has so much power over tariffs and the economy, the role immigrants play in our economy, why fertility is falling across the world, and how much weather forecasters can impact the economy. Segment […]

Wintrust Business Lunch
Wintrust Business Lunch 7/10/25: Copper tariff, Nvidia, global quantum forum, side hustle decline

Wintrust Business Lunch

Play Episode Listen Later Jul 10, 2025


Segment 1: Jared Dillian, Best selling financial author of the new book, ‘Rule 62: Meditations on Success and Spirituality,' joins John Williams the latest rounds of tariffs including the tariff on Brazil and copper. Jared also explains his journey of writing his newest self-help book. Segment 2: Bree Fowler, Senior Writer, CNET, joins John Williams to talk […]

Wintrust Business Lunch
Wintrust Business Lunch 7/9/25 – Terry Savage: The impact of Trump's budget bill

Wintrust Business Lunch

Play Episode Listen Later Jul 9, 2025


Nationally syndicated financial columnist and author Terry Savage joins John Williams to talk about what we need to know about Trump’s Big Beautiful Bill. Terry explains what the bill does, what it doesn’t do, and to clear up confusion about taxes and social security benefits. And as always, Terry answers all of your financial questions. And John and Terry […]

Business Lunch
High-Impact Offers: Strategies for Sales Success

Business Lunch

Play Episode Listen Later Jul 4, 2025 35:21


Welcome to a new episode of Business Lunch. In this episode, Ryan Deiss and I dive deep into the art of creating effective offers and adapting sales strategies for different business models. From navigating the challenges happening because of rising ad costs to understanding the nuances of sales motions, we share valuable insights and practical tips. Whether you're selling high-ticket items or aiming to optimize online conversions, this episode is packed with advice to help you convert successfully .Highlights:"Sales motion impacts offer structure.""You've got to say at what point in this process do we get agreement on the problem? Because there's got to be problem agreement before anything else.""If you can understand levels of awareness, you understand probably 80% of what you need to know to be really good at sales and marketing."Timestamps:00:00 - Problem Agreement04:05 - Shifting Sales Strategies05:07 - Sales Motion and Offer Structure07:30 - Ad Cost Challenges10:00 - Sales Assist and Sales Function11:45 - Levels of Awareness13:20 - Problem Awareness to Solution Awareness14:40 - Crafting Effective Lead Magnets15:50 - Adapting to Market ChangesCONNECT • Ask Roland a question HERE.RESOURCES:• 7 Steps to Scalable workbook• Get my book, Zero Down, FREETo learn more about Roland Frasier

Business Lunch
Don't Get Killed by the Hype - AI Gadgets Failing to Deliver

Business Lunch

Play Episode Listen Later Jul 1, 2025 32:13


Welcome to a new episode of Business Lunch, Ryan Deiss and I dissect the recent hype surrounding two new AI-powered gadgets - the Humane AI pen and the Rabbit. Both products promised to revolutionize our lives with features like real-time feedback and enhanced productivity. However, reviews have been scathing, exposing the devices as clunky, unhelpful, and ultimately a letdown. We delve into the challenges of launching new hardware products in a crowded market and explore the dangers of overpromising and failing to deliver, highlighting how a great marketing campaign can backfire if the product itself isn't exceptional.Highlights:"The people are not stupid long term, we're all a little stupid short term from time to time.""It's a game of replacement, not enhancement.""The better you are at marketing, the better your product better be.”Timestamps:00:54 - Introduction02:36 - Memorial Day05:26 - AI Devices and Hype07:17 - The Future of AI Gadgets12:24 - Apple Vision Goggles14:21 - Lessons Learned16:30 - Nobody Wants More Stuff17:32 - Rabbit Using Chat GPT23:10 - Marketing Lessons (and Mistakes)CONNECT • Ask Roland a question HERE.RESOURCES:• 7 Steps to Scalable workbook• Get my book, Zero Down, FREETo learn more about Roland Frasier

Business Lunch
The Ethics of Outsourcing Yourself

Business Lunch

Play Episode Listen Later Jun 27, 2025 37:02


Welcome to a new episode of Business Lunch! In this episode, Roland Frasier and Ryan Deiss tackle the controversial topic of 'shadow standards' in the workplace. They explore the ethics and implications of employees outsourcing their own jobs to other workers, often in other countries, without their employers' knowledge. The discussion touches on the legal, ethical, and practical ramifications of this growing trend and offers insights into how both employees and employers can navigate this complex landscape.Highlights:"Employees are outsourcing their jobs, effectively becoming mini-agencies themselves.""Is it deceptive if you wouldn't proudly announce what you're doing?""Good employers will always support efficiency and innovative ideas.""Outsourcing your job without transparency is setting yourself up for liability."Timestamps:00:00 - Introduction 01:12 - The Great Resignation and Quiet Quitting02:49 - Ethical Dilemma: Outsourcing Personal Jobs05:30 - Employer Perspective on Shadow Standards08:49 - Legal and Security Implications12:19 - Hypocrisy and Exploitation in Shadow Work14:41 - Building a Team Ethically and Transparently18:35 - Crucial Policies and Handbook Updates20:31 - Encouraging Transparent Efficiency23:02 - The Problem with Shadow Work24:37 - The Value of High-Level Employees30:55 - Conclusion and TakeawaysCONNECT • Ask Roland a question HERE.RESOURCES:• 7 Steps to Scalable workbook • Get my book, Zero Down, FREETo learn more about Roland Frasier

Business Lunch
The Art of the Deal: Disruptive Strategies for Business Growth

Business Lunch

Play Episode Listen Later Jun 24, 2025 22:35


Welcome to a new episode of Business Lunch! This episode is a deep dive into how unconventional thinking and strategic agility can transform business challenges into powerful growth opportunities. With a focus on creative deal-making, innovative funding strategies, and the art of leveraging constraints, this episode provides listeners with actionable insights and inspiration to rethink their approach to business. Perfect for entrepreneurs at any stage, this conversation illuminates the path to unlocking the potential within your business, revealing the blueprint for achieving breakthrough success and sustainable growth.Highlights:"The most promising opportunities often start as average propositions that require work to uncover their true value.""Tailored expertise can open up new opportunities in deal-making, transforming constraints into strategic advantages.""Creative solutions often outshine straightforward financial injections, paving the way for long-term success and growth."Timestamps:00:29 - "Behind-the-Scenes Business"01:27 - "Innovative Deal Structuring"04:22 - "Exploring Funding Options"06:18 - "Uncovering Value in Opportunities"08:16 - "Addressing Key Growth Bottlenecks"10:44 - "Expertise in Eliminating Constraints"11:14 - "Funding Through Sales Innovation"14:08 - "Inventory Challenges in E-Commerce"19:22 - "The Power of Creative Solutions"24:43 - "Speculating Future Growth"Mentioned in this episode:Get Roland's Training on Acquiring Businesses!Discover The EXACT Strategy Roland Has Used To Found, Acquire, Scale And Sell Over Two Dozen Businesses With Sales Ranging From $3 Million To Just Under $4 Billion! EPIC Training

Business Lunch
The Exit Trap: What Most Founders Miss When It's Time to Sell

Business Lunch

Play Episode Listen Later Jun 17, 2025 74:27


Welcome to a New Episode of Business Lunch! In this episode, Roland Frasier and Ryan Deiss dive deep into the world of mergers, acquisitions, and private equity. They share insider strategies for selling your business, from understanding platform vs. tuck-in acquisitions to negotiating multiples and avoiding common pitfalls. Whether you're a founder considering an exit, a business owner curious about private equity, or just looking to maximize your company's value, this conversation is packed with actionable insights..Highlights:"People don't buy services, they buy better versions of themselves.""You want to be the platform company, not the tuck-in acquisition.""Private equity is fishing to avoid a process, don't take the first offer.""The more you prove you can acquire and integrate, the higher your multiple."Highlights:00:00 Introduction and Setting the Scene06:05 Facilitators Appreciation and Round Table Rumble07:09 Discussion on Exits and Private Equity08:57 Understanding Private Equity Deals15:57 Negotiation Strategies and Mistakes to Avoid27:06 Preparing for a Successful Exit33:33 Maximizing Company Value for Acquisition37:37 Current Market Trends and Multiples41:27 Strategic Considerations for Selling Your Business46:09 Navigating Acquisition Offers and Due Diligence01:05:25 Connecting with Potential Buyers and Investors01:07:50 Introducing Deanna Rogers and Closing RemarksCONNECT • Ask Roland a question HERE.RESOURCES:• 7 Steps to Scalable workbook • Get my book, Zero Down, FREETo learn more about Roland Frasier

Business Lunch
Wealth, Work, and What Matters Most

Business Lunch

Play Episode Listen Later Jun 10, 2025 24:47


Welcome to a new episode of Business Lunch! In this episode, Ryan Deiss and I delve into the intricate dance between pursuing success and nurturing personal life. As entrepreneurs, the quest for a meaningful legacy often leads us down a path of extremes. We talk about some insights on finding equilibrium amidst the chaos of business growth, family commitments, and personal health. Whether you're scaling the heights of your career or seeking satisfaction in the simple things, this conversation offers valuable perspectives on prioritizing what truly counts.Highlights:"Be intentional about your seasons...that's important.""As long as I'm remembered by the kids, I'm good. It's such an ego thing to me." 3. "Being intentional about what you're doing...you're probably going to be okay." Timestamps:00:00 -Weather & Life's Storms02:22 -The Legacy Question05:55 -Wealth vs. Health07:20 -Entrepreneurial Extremes09:05 -Life's Balancing Act10:00 -Yearly Planning for Balance14:00 -Practical Balance Tips16:02 -Wealth's Diminishing Returns18:08 -100 Million: A Turning Point?20:50 -Legacy's Ephemeral NatureCONNECT • Ask Roland a question HERE.RESOURCES:• 7 Steps to Scalable workbook • Get my book, Zero Down, FREETo learn more about Roland Frasier