Tim is a go-to thought leader in investing in startups, entrepreneurship and related topics in both Southwest Florida and the entire Sunshine State. In addition to being a partner at Fifth Avenue Family Office in Naples, which works with a select group of high net-worth families, Tim is also chair of the Tamiami Angel Funds. Tim has been named to Florida Trend magazine’s list of Florida’s 500 Most Influential Business Leaders six times and was named a 2025 Business Hall of Fame Laureate by Junior Achievement of Southwest Florida. On this episode, Business Observer Managing Editor Mark Gordon and Tim talked about what being fired taught him about the leader he wants to be. They also talked about the do's and don’ts of making good investor presentations and how a startup entrepreneur can know when he or she is getting to yes.   3 Takeaways: (14:10) Leaders are successful because of the teams they build (18:45) Failure happens when you are trying to do great things, you need resilience (22:30) Storytelling is art and science Timestamps: (00:00) Introducing Tim Cartwright, Partner and Co-Founder, Fifth Avenue Family Office (06:20) What is Fifth Avenue Family Office and Tamiami Angel Funds? (08:35) What have you learned from working with leaders of these organizations? (13:55) What defines good leadership? (16:25) Who influenced your leadership style? (18:00) Resilience and overcoming setbacks (21:00) What role does storytelling play in leadership? (24:15) What is the biggest “not to do” in pitching a business (26:00) What is on the horizon for your entities? Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Global business brokerage Transworld Business Advisors is based in South Florida, with a heavy presence on the west coast of the state. Andy Cagnetta, after owning and running a pasta shop in Connecticut, joined Transworld in 1995. In 1997, driven, his bio says, “by his entrepreneurial spirit and belief in the industry’s potential, he purchased the company.” Transworld now has multiple Florida offices, including one in Tampa, and a global presence, from the Middle East to Mexico. On this episode, Business Observer Managing Editor Mark Gordon and Andy talked about what he wants his leadership legacy to be (it’s short and sweet) and how he leads high-performing teams. They also talked about some of his charitable work, which includes cooking a lot of pasta.  3 Takeaways: (07:40) Successful business owners are not afraid to do the gritty work (08:30) Have a high tolerance for pain with people (17:00) In a negotiation, not everything is about money Timestamps: (00:00) Introducing Andy Cagnetta, CEO, Transworld Business Advisors (04:30) What is Transworld Business Advisors? (05:40) How did you get into this line of work? (07:00) What have you learned from other leaders? (09:05) Balancing employee pain points (10:50) Who are your influences? (13:30) Storytelling in leadership (14:30) Something you wish you knew earlier? (15:30) What do you look for in leaders? (16:45) Negotiating tips (19:45) What legacy do you want to leave? (21:15) Transworld Business Advisors in 2026 Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

John Burpee has been in the Florida commercial real estate market for more than 30 years. He consults with national investment firms, financial institutions and private investors, and has brokered more than $2.1 billion in commercial investment real estate deals. He’s also president of the Florida Gulfcoast Commercial Association of Realtors, and has worked as a court-appointed receiver. On this episode, Business Observer Managing Editor Mark Gordon and John talked about his mentors, what he has learned from working for some high-achieving executives and how he approaches difficult conversations.  3 Takeaways: (10:20) If the deal is right, buyers come from all over (11:30) Put the buyer and seller in the room together (14:25) You stay even with your competition Monday through Friday, 9-5. You get ahead of them every minute before and after that. Timestamps: (00:00) Introducing John Burpee, President & CEO, John Burpee & Associates (04:45) What is John Burpee & Associates? (06:15) Leadership insights (09:20) Managing the operations and leadership (10:50) Learning lessons (12:35) Dealing with conflict (14:00) Lessons from Grandfather (15:25) What legacy do you want to leave? (17:15) The market in 2026

Erin McLeod has worked in public relations, communications, consulting, health care, hospitality and the club industry. She’s been with the Senior Friendship Centers in Sarasota since 2004; she has been CEO of the nonprofit since 2015. On this episode, Business Observer Managing Editor Mark Gordon and Erin talked about her career origins and how she, on the spot, thought of a top-notch acronym on the spot in a job interview several years ago. She called it CPR, when asked what she would bring to the organization: Communication, professionalism and relationships. Erin and Mark also talked about the connections between being an accountable parent and an accountable leader. 3 Takeaways: (12:20) This is not a sprint, it’s a marathon (15:00) Dream big, get stuff done, have fun, no drama (17:00) The quicker you address tough situations the better Timestamps: (00:00) Introducing Erin McLeod, President & CEO of Senior Friendship Centers (04:15) What is Senior Friendship Centers? (06:10) How did Erin get to Senior Friendship Centers? (08:40) What does leadership mean to you? (10:50) Who influenced your leadership style? (12:40) Balancing your employee’s work style (15:40) Approach to leadership you wish you knew earlier? (16:40) Addressing conflict (20:40) Storytelling in leadership (22:30) Imposter syndrome (23:40) Senior Friendship Center in 2026 Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Dara Shareef is the managing partner of Benchmark International, where he oversees the transaction team in the firm’s U.S. headquarters in Tampa. Benchmark recently made a big splash in the region, in signing a naming rights deal for what’s now Benchmark International Arena, home of the Tampa Bay Lightning. On this episode, Business Observer Managing Editor Mark Gordon and Dara talked about lessons in empathy and grit he learned from his mother and high school football coach, respectively, and how to grow into being a decisive leader. They also talked about his methods of conflict resolution and helping to get people on opposing sides to reach consensus.  3 Takeaways: (10:00) Leadership is about accountability (15:05) Don’t place artificial limits on yourself (18:30) Deal with conflict head on and in the moment Timestamps: (00:00) Introducing Dara Shareef, Managing Partner, Benchmark International (04:20) What is Benchmark International? (06:20) Winning naming rights for the Tampa Bay Lightning's arena (07:45) How did Dara get into this field? (10:00) What does leadership mean to you? (11:10) Influences in leadership (13:00) Growing up (14:20) Lessons from playing football (16:00) Tough decisions that shaped Dara’s career (18:15) Handling conflict (21:00) Leadership advice (23:30) What legacy do you hope to leave? (25:00) What is coming for Benchmark International? Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Sophia Shaw has had many interesting roles, from leading the Chicago Botanical Garden, to being an Adjunct Professor at the Kellogg School of Management. After all that, her work is just getting started. On this episode, Business Observer Managing Editor Mark Gordon and Sophia talk about Sophia's start up, PlanPerfect, her 'why' to get into nonprofit work, the importance of planning to plan and why initiative is a crucial leadership characteristic. They also talked about the times she’s struggled with Impostor Syndrome, and how she’s gotten over it. 3 Takeaways: (07:45) Leaders need to understand what it takes to execute strategy (12:15) When conflict arises, go back to the strategic plan (14:00) Most people want to go to work knowing what they have to do Timestamps: (00:00) Introducing Sophia Shaw, co-founder, PlanPerfect (03:30) What is PlanPerfect? (04:30) Why did you start PlanPerfect? (07:45) What are must-have leadership characteristics (09:20) Knowing your “why” (10:20) Learning from mistakes (12:00) Working through conflict (15:30) Sophia’s leadership influences (17:10) Handling imposter syndrome (19:50) What does Sophia look for in good leaders? (21:10) Plan Perfect in 2025 Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Doug is the executive director of the Child Protection Center of Sarasota, a nonprofit dedicated to prevention, intervention and treatment of child abuse. Doug has been with the organization for 30 years, and it has led it since 2011. On this episode Business Observer Managing Editor Mark Gordon and Doug talked about his career transition in going from the U.S. Army to social work; what he looks for in young leaders; and how he builds resilience into his leadership approach when working in an emotionally-challenging field. They also talked about one of their favorite non-work topics: baseball, and their favorite teams.    3 Takeaways: (14:00) You have to adapt to overcome challenges (16:00) Honesty, integrity, and servant leadership are Doug’s must-have leadership characteristics (17:50) Be a willing to make decisions and follow through Timestamps: (00:00) Introducing Doug Staley, Executive Director, Child Protection Center (07:50) 30th anniversary at Child Protection Center (10:10) What is the Child Protection Center? (13:30) Handling leadership challenges (16:00) Leadership characteristics (17:30) Leadership advice (21:30) Overcoming setbacks (23:35) Child Protection Center in 2025 Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Bob has been president and CEO of Smith & Associates for some 30 years. The firm is one of the largest independent real estate brokerage firms in the Tampa Bay region, selling properties in St Petersburg and Tampa. The firm has also helped bring more than 40 upscale developments to the region. On this episode Business Observer Managing Editor Mark Gordon and Bob talked about how Bob has adapted to three decades of big changes in big-ticket real estate sales. They also talked about his go-to leadership characteristics and his go-to mentors.  3 Takeaways: (10:45) Leaders need to have empathy (12:50) The truth 100% upfront is always best (17:30) You need to give back to the community Timestamps: (00:00) Introducing Bob Glaser, CEO, Smith & Associates (04:30) How Bob got into real estate (08:00) How Bob adjusts to changes (10:25) What do you look for in leaders? (11:50) How have you evolved as a leader? (13:10) Leadership advice (14:45) Handling “gray areas” (16:20) Mentors (18:15) Overcoming setbacks (19:40) Smith & Associates in 2025 Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Shep has been CEO of the Jewish Federation of Sarasota-Manatee since 2021. He previously worked for Federations in Pittsburgh and Cincinnati; in Ohio he was CEO of the Jewish Federation of Cincinnati for 16 years. Prior to Federations, Shep, an attorney, worked for a Washington, D.C. law firm that worked for nonprofit clients. On this episode Business Observer Managing Editor Mark Gordon and Shep talked about building community consensus even when it seems super-difficult, hiring good people and not micromanaging and leading with a clear vision.  3 Takeaways: (07:45) Create a compelling vision and give people the experience they are looking for (11:45) If you have made up your mind, move forward (15:45) Attach your ego to the whole organization Timestamps: (00:00) Introducing Shep Englander, CEO, Jewish Federation of Sarasota-Manatee (06:10) Growth and turnaround in Cincinnati  (08:10) How do you get people on the same page? (09:20) Who are your mentors? (11:30) The importance of clarity (13:40) Leadership advice (14:55) What do you look for in leaders? (16:45) Overcoming setbacks (18:00) What is coming up in 2025? Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Ian Schmoyer has helped lead the homebuilding company he founded eight years ago, Christopher Alan Homes, to become both one of the largest privately-owned homebuilding firms in Lee County and a top 100 firm nationwide. The company, with a focus on amenable and affordable homes, builds in Charlotte and Lee counties in Southwest Florida and Palm Bay on Florida's East Coast. On this episode Ian and Business Observer Managing Editor Mark Gordon talk about the genesis of Ian’s core hiring rule: never hire jerks. They also talk about his mentors, like his dad, and his views on a hot button issue: housing affordability in Florida.          3 Takeaways: (09:10) Culture is the most needed thing in business today (11:40) Your word is gold (14:40) A lot of successful people kept it simple Timestamps: (00:00) Introducing Ian Schmoyer, Chairman, President & CEO, Christopher Alan Homes (06:25) Why did you get into obtainable housing? (08:00) What defines Christopher Alan Homes' culture? (10:10) What leadership characteristics are important to you? (11:30) Leadership advice (12:20) Ian’s mentors (14:00) Book recommendations (15:05) Overcoming setbacks (16:30) Magic Wand solution to affordable housing (17:45) Christopher Alan Homes in 2025 Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Greg Slater has had a 30-year career in highways and transportation, the last three or so in Tampa as CEO of the Tampa Hillsborough Expressway Authority. Before that he was the Maryland Secretary of Transportation. His current organization, THEA, recently approved a $752 million work plan, which will include projects for safer streets and congestion relief. On this episode Greg and Business Observer Managing Editor Mark Gordon talked about one of his key advice nuggets for young people: say yes to every opportunity and create your own luck. They also talked about his mentors and what he looks for in leaders.  3 Takeaways: (12:30) Always be a student (20:00) Be a force multiplier, someone who makes everyone else better (23:30) The path forward is never a straight line Timestamps: (00:00) Introducing Greg Slater, CEO, Tampa Hillsborough Expressway Authority (05:00) What is the Tampa Hillsborough Expressway Authority? (06:25) About Greg’s career, becoming Secretary of Transportation of Maryland (12:15) A little luck and taking on roles others will not (14:15) Attacking a job with a large leadership role (16:45) Mentors (19:10) What do you look for in leaders? (20:55) Dealing with setbacks (24:10) What is coming up in 2025? Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Kevin Gillen has been a market president for Synovus Bank in Florida since 2020, covering the Tampa Bay and Sarasota-Manatee markets, among other regions. He previously held banking leadership positions for financial institutions in New Jersey and the Washington, D.C. area. On this episode Kevin and Business Observer Managing Editor Mark Gordon talk about the winding path of Kevin’s career and what has driven him to be a better leader at each bank and organization he has worked for. They also talked about what he looks for in hiring and promoting leaders.   3 Takeaways: (10:00) Passion and a people-first mindset are crucial for leadership (12:15) Great leaders cannot bring their ego into decisions (14:50) Sometimes it is better to sleep on a decision Timestamps: (00:00) Introducing Kevin Gillen, Market President, Synovus Bank (03:00) How Kevin got into banking (05:20) Getting to Synovus Bank and about Synovus Bank (09:45) Learning about leadership from his clients (12:05) What do you look for in leaders? (13:25) Working with an open door policy (14:35) Great leadership advice (15:40) Overcoming setbacks as a banker (18:20) Mentors over Kevin’s career (22:00) Synovus Bank in 2025 Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Jerel McCants is a leading architect in the Tampa Bay market, having built his own firm from scratch with a focus on how people use spaces. He founded the company in 2010, and it focuses on commercial and residential builds, with work on the both coasts of Florida. On this episode Jerel and Business Observer Managing Editor Mark Gordon talk about his philosophy of designing spaces that bring people together and how and why he launched his own company. And listen for the pop culture icons Jerel would love to have dinner with.  3 Takeaways: (08:45) You can find mentors in unexpected places (12:00) Be curious, there is always something you can take from a conversation (15:10) Great leaders take responsibility Timestamps: (00:00) Introducing Jerel McCants, founder, Jerel McCants Architecture Tampa (03:45) What kind of work does Jerel McCants Architecture Tampa do? (05:10) How did Jerel get into Architecture? (06:10) Jerel’s role in Tampa Union Station (08:00) Jerel’s mentors (12:00) Being a curious leader (15:00) Leadership characteristics (17:20) Best leadership advice (18:50) Favorite project Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Brittany Lamont was named president and CEO of the Lakewood Ranch Business Alliance in 2021. Prior to that Lamont, a vocal advocate for the local business and civic communities, was a vice president at the Sarasota Chamber of Commerce. On this episode Brittany and Business Observer Managing Editor Mark Gordon talk about her career in chambers of commerce and what motivates her. They also talked about what she looks for in leaders, her mentors and how she shapes the work culture at the LWRBA.  3 Takeaways: (07:15) Be a servant leader, support your staff (08:40) When you have a small team, you need to know what makes everyone click (13:00) It is important to have a tribe that support each other Timestamps: (00:00) Introducing Brittany Lamont, President & CEO, Lakewood Ranch Business Alliance (02:50) What is the Lakewood Ranch Business Alliance? (04:00) Brittany’s career (05:30) Leadership lessons and being able to learn from so many leaders (07:05) Characteristics of good leaders (08:10) What does servant leadership mean to you? (11:40) Mentors and lessons you have learned (16:00) Taking your ego out and listening to feedback (17:45) LWRBA in 2025 Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Michael Corley worked in health care and human resources for some 10 years before starting his own leadership consulting business, The Corley Co., in 2009. The Corley Co. works with nonprofit and some for-profit leaders, in addition to nonprofit boards on topics like creating engaged board members; bringing clarity to roles and responsibilities; and developing strategic focus areas. On this episode Michael and Business Observer Managing Editor Mark Gordon talked about how he got into podcasting, the valuable lessons he learned from his father and other mentors and what he learned from getting laid off from a high-level corporate job.  3 Takeaways: (08:30) Leadership is not that different in a for-profit versus nonprofit (12:15) Great leaders have humility, make decisions, and communicate clearly (15:10) Never burn a bridge Timestamps: (00:00) Introducing Michael Corley, President of The Corley Company (03:10) What is The Corley Company? (05:20) Developing your ability to become a thought-partner (06:20) About I501(c)You - The Podcast for Nonprofit Board Members (08:15) What have you learned about leaders from your interviews on I501(c)You? (10:20) Michael’s Career (11:55) What are some good leadership characteristics? (14:00) How do you handle setbacks? (15:00) Mentors (16:35) How do you overcome setbacks? (19:40) The Corley Company in 2025 Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Erika Donalds was a COO and CFO for financial services firms before shifting gears to education, first as a mom and later as an elected Collier County School Board Member. She’s since led and supported several innovative educational models, including one of the world’s first virtual reality schools, Optima Academy Online. On this episode Erika and Business Observer Managing Editor Mark Gordon talked about the why behind her career change and why she has remained a leader in education transformation. They also talked about her mentors and the characteristics of top-flight leaders.  3 Takeaways: (09:55) Have high expectations for your employees and team (14:30) Decide what success is going to look like alongside your employees (17:30) Look at the big picture when thinking about setbacks Timestamps: (00:00) Introducing Erika Donalds, founder and chairman, Optima; education entrepreneur (05:00) What is Optima Ed? (06:45) Center for Education Opportunity (08:00) Starting in Finance and leading to education (09:30) What Erika learned about being a good leader working in finance (12:00) How do you lead? (14:05) What do you look for in leaders? (16:10) How do you overcome setbacks? (18:45) What is next for your organizations? Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Kaitlyn Perez launched her own business, KPC Strategies, in January 2024. Prior to that she was senior director of communications and marketing with the National Policing Institute and community affairs director for the Sarasota County Sheriff’s Office for nearly seven years. On this episode Kaitlyn and Business Observer Managing Editor Mark Gordon talk about her career change, in going from top law enforcement spokesperson to running her own crisis management firm that helps leaders navigate high-stakes issues. They also talked about what she learned working directly with elected sheriffs and the dos and don'ts of crisis management.   3 Takeaways: (13:00) Define don't defend (17:30) Speak to yourself like you would your 4-year old self (19:30) Failures are learning lessons Timestamps:  (00:00) Introducing Kaitlyn Perez, founder and CEO, KPC Strategies (03:40) What is KPC Strategies? (05:20) Working for the Sarasota County Sheriff’s Office (07:05) Getting into this line of work (08:15) Mentors (09:45) Crisis Communication Must Do’s (11:55) What should you NOT do in a crisis? (13:00) Define don't defend (14:45) What have you learned about leadership? (17:30) Speak to yourself like you would your 4-year old self (18:40) Overcoming setbacks (21:15) KPC Strategies in 2025 Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Chris Cunningham, owner of a True-Value hardware store in Tampa and a commercial real estate investor, started his career in lending and financial services. But he soon learned he wanted to do his own thing, and has spent the past 15 years building and buying complementary businesses. On this episode Chris and Business Observer Managing Editor Mark Gordon talk about his mentors and how he learned about work ethic and how to treat people. And listen for his secrets on how to outdo the competition.  3 Takeaways: (10:20) Don’t put yourself in a bucket (13:15) AQ is the most important thing for business owners and leaders (adversity quotient) (17:15) The bigger the problem you can solve, the more you will get paid Timestamps: (00:00) Introducing Chris Cunningham, owner, True Value America Store & Dry 24 Water Restoration (03:55) Chris’ Career (05:30) Chris’ inspiration to become an entrepreneur (06:35) Tell us about True Value America and Dry 24 Water Restoration (10:00) Keys to being a successful entrepreneur (12:00) Retail deserts and getting involved in the community (12:55) What do you look for in good leaders? (14:00) How do you respond to setbacks? (17:45) What did you learn from your grandparents? (20:00) What is coming up in 2025? (21:55) Advice for young entrepreneurs Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Helene Lotman has been in the nonprofit human services space for 40 years, and is currently CEO of JFCS of the Suncoast, which works with people in need in a variety of demographics in a non-dominational setting. Helene has worked in Kansas City, Palm Beach and other spots, in addition to an earlier stint in Sarasota. On this episode Helene and Business Observer Managing Editor Mark Gordon talk about how she holds the staff accountable and has built a culture of accountability at the nonprofit organization. And listen for Helene’s steps she took to get the organization on better financial footing.  3 Takeaways: (05:20) Listen before you act (06:40) The culture makes the organization (12:30) Good leadership is unique Timestamps: (00:00) Introducing Helene Lotman, President and CEO, JFCS of the Suncoast (02:40) What is JFCS? (04:00) Helene Lotman’s career (05:20) Step taken to turn around the organization (07:00) Steps to change the culture (09:30) Hugs and High Fives with Helene (10:55) How do you set up your work day while having an open door policy? (12:30) Leadership characteristics (14:40) Be bold (15:30) Hiring A-list employees (17:20) Overcoming setbacks (19:30) JFCS in 2025 Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.

Justin Papadakis has spent his career in real estate development and soccer, with his most recent position being a bit of both: deputy CEO and chief real estate officer of the United Soccer League, based in Tampa. On this episode Justin and Business Observer Managing Editor Mark Gordon talk about what he learned about leadership from playing soccer — he was a goalie — and the steps the USL is taking to build its brand.    3 Takeaways: (09:20) Be aware of the external issues (11:00) Great leadership is the ability to innovate and execute on an idea (15:00) Limit your unforced errors Timestamps: (00:00) Introducing Justin Papadakis, Deputy CEO & Chief Real Estate Officer, United Soccer League (05:00) Justin before joining USL (07:30) Favorite part of working at USL (08:45) Challenging aspects of working at USL (10:20) Characteristics of good leadership? (12:35) Mentors (13:50) Overcoming setbacks (17:30) USL in 2025 and beyond Join us every week as we interview business leaders to learn what makes them great, what they look for in growing leaders, and much more. Visit businessobserverfl.com for more.