Welcome back to Life from Within. In this episode, I chat with Lara O'Connor Hodgson, the CEO of ROXWrite. We talk about her journey as a contrarian thinker and how her background in aerospace engineering shaped her unique approach to solving complex problems in startups.

We also discuss how to foster innovation, the importance of doing something different and how she is currently using AI to revolutionize risk assessment in the lending world. If you’ve ever wanted to challenge the status quo in your organization, this episode is for you.

💡 Key Takeaways:

• How to navigate business challenges that feel overwhelming.
• How to create a safe space for teams to experiment and ideate without fear.
• How ROXWrite is leading the lending industry by using AI to look at risk through a completely different lens.
• How to build the muscle for navigating uncertainty in your own career.

Chapters

00:00 | Introduction to Engineering Mindset and Liberal Arts Personality

04:40 | The Strengths and Weaknesses of Compassionate Leadership

06:34 | Hiring for Mindsets vs. Skill Sets

11:55 | Navigating Team Dynamics and Cultural Fit

18:05 | Developing Comfort with Conflict in Leadership

24:09 | The Importance of Intentional Culture

26:09 | The Difference Between the Collective Person and Individuals

31:40 | Introducing ROX Write: A New Venture

38:30 | The Role of a CEO in Team Building

Guest

Lara Hodgson currently serves as the CEO of RoxWrite, an innovative, AI-enabled underwriting platform to enable lenders and businesses to assess the risk of their customers. She is a rocket scientist, a contrarian and a serial entrepreneur with an engineering mind and a liberal arts personality, having founded 3 companies, Insomnia LLC, Nourish and NowAccount, prior to Rox. Before starting her first company, she worked at startups such as Dunk.net, founded with Shaquille O'Neal and at iXL where she learned she thrived in the ambiguity of start-ups. Lara is co-author of the best-selling book, "Level Up: Rise Above the Hidden Forces Holding your Business Back" and has served as an Entrepreneur-in-Residence at Harvard Business School. She serves as a Trustee at Georgia Tech where she studied Aerospace Engineering and was a member of the Varsity Track and Field Team.

LinkedIn: https://www.linkedin.com/in/larahodgson

X: @laraohodgson

Instagram: https://www.instagram.com/level.up.2day/

Level Up Book: https://www.amazon.com/Level-Up-Hidden-Holding-Business/dp/0593539826

Host

Kelly Dwyer is an executive coach and facilitator. Through her podcast Life from Within, she opens up real conversations about personal growth, career crossroads, and the inner work of leadership. She created the show to explore the moments of courage and clarity that spark inner shifts and lead to meaningful outer progress.

In her coaching and facilitation practice, Kelly partners with thoughtful, influential leaders, including founders, C-suite executives, and rising leaders who shoulder significant responsibility and want to lead with grounded clarity and self-trust. She helps them return to what matters most, cut through the noise, and navigate inflection points with aligned conviction.

Kelly is a graduate of the University of Colorado and holds an MBA from Cornell...

Welcome back to Life from Within. How do you transition to the next version of yourself when you achieve everything you thought was impossible, only to find a hollow feeling inside? In this episode, I am joined with Beck Sydow, a self-described "business geek with Buddhist roots." Beck shares their journey from a 20-year corporate career at UPS to leading Sticker Giant as COO through a period of massive growth and an eventual private equity sale.

Beck discusses the heartbreak in leadership, the difference between effort-based burnout and values-based burnout, and why the most precious times in our lives are often the transitions we try to rush through.

• How the practice of meditation translates to how you respond to conflict in your daily life.
• Why networking is a marathon, not a sprint.
• How to have honest, human conversations with employees when they are struggling to meet new expectations.
• How they managed 30%+ growth plans during a global pandemic and the eventual sale of Sticker Giant to Private Equity (PE).
• How to stop rushing through life’s transitions
• How to recognize fear disguises and what is behind them

Chapters

00:00 | Exploring Buddhist Roots and Personal Journey

06:28 | Navigating Corporate Leadership and Growth Challenges

12:40 | The Heartbreak of Leadership and Human Connection

16:29 | Personal Identity and Transitioning

20:41 | Uncovering Hidden Challenges in Business Purchases

22:41 | The Different Levels of Burnout

24:50 | The Pain and Beauty of Transition

28:11 | Understanding Fear with Compromising

29:50 | The Journey of Remaking Yourself

35:45 | Befriending Your Experience

Guest

Founder, Business Advisor & Leadership Coach

Beck Sydow (they/them) works with leaders who are brilliant, overloaded, and tired of losing themselves under pressure. A business geek with Buddhist roots, Beck teaches founders, entrepreneurs, and senior leaders to recognize fear in real time, steady their nervous system, and return to clarity when it matters most.

With four decades of experience as a CEO/COO, therapist, and mindfulness teacher, Beck moves easily between business strategy and the inner workings of a leader’s nervous system. This dual fluency is what clients call “magic”—the moment when reactivity quiets, insight returns, and leadership feels spacious again.

Beck’s work offers a way of leading where results and humanity can finally coexist. They are the Founder of HumanKind Business Leaders and the creator of the People-Hearted & Business-Minded™ framework.

Beck’s LinkedIn: https://www.linkedin.com/in/becksydow/

Human KindBusiness Leaders: https://www.humankindbusinessleaders.com/

Brene Brown’s New Book: https://brenebrown.com/book/strong-ground/

Host

Kelly Dwyer is an executive coach and facilitator. Through her podcast Life from Within, she opens up real conversations about personal growth, career crossroads, and the inner work of leadership. She created the show to explore the moments of courage and clarity that spark inner shifts and lead to meaningful outer progress.

In her coaching and facilitation...

How do you move from a $19,000-a-year entry-level recruiter to the CEO of a private equity-backed IT staffing firm? In this episode, Matthew Ripaldi, CEO of Talent Groups, shares his 26-year journey through the technical staffing industry.

Matthew shares his motivation behind recruiting, the isolating pressure of the CEO chair, and the high-speed execution required in the world of Private Equity (PE). We discuss his startup experience, the challenge of integrating five companies into one brand, and the humbling experience of receiving a 12-page 360 review. Matthew’s insights on trust, delegation, and being open to learning can benefit you whether you are an aspiring leader or a seasoned executive.

• Matthew recalls the moment he found his why—helping a candidate land a life-changing job that allowed him to buy his first home. This core passion for putting people to work has fueled his 26-year career.
• After promising his mother he would try a startup, Matthew realized he thrived in high-energy environments. He discusses the importance of self-awareness in knowing where you do your best work.
• Operating a PE-backed company involves a unique speed of execution, especially when working in a leveraged environment with debt obligations and clear exit targets.
• As a CEO, Matthew views himself as reporting to his employees rather than the other way around.
• Matthew opens up about his 360 review. He explains why leaders must create a culture where teams feel safe telling them what they need to hear, not what they want to hear.

Chapters

00:00 Introduction to Talent Groups and Career Journey

07:35 Transitioning to CEO Role and Responsibilities

12:29 Decision-Making as a CEO

18:16 Challenges in a Changing Industry

21:35 Integration and Operating in a Leveraged Environment

22:28 Navigating the Challenges of First-Time CEO

25:56 The Importance of Delegation and Trust

30:23 Building Trust Through Feedback and Reflection

33:23 Focusing on Execution and Delivering Results

37:05 The Role of Project Management in Execution

38:11 Finding Passion in Your Career

Guest

Matthew James Ripaldi is an accomplished staffing industry veteran with over 20 years of experience. During his first 18 years in the industry Matthew worked for The Adecco Group, a Global Fortune 500 Company and the world’s second largest staffing firm. Starting off as a Technical Recruiter and quickly finding his passion for the business. This passion combined with a strong work ethic and consistent high-performance helped him excel to seven (7) consecutive promotional opportunities, holding executive leadership roles across eight (8) different industry leading brands; TAD Technical, Adecco Technical, Ajilon ICT, Ajilon Consulting, VendorPass, Modis IT, Modis Engineering and Modis Managed Solutions. Matthew’s vast early experience led to extensive knowledge across contract staffing, direct hire, managed services, project based solutions, onsite MSP programs, payrolling, training and development, and global client solutions.

Matthew then joined Collabera as Executive Vice President in September of 2017 reporting directly to the Founder, Chairman and CEO of this fast growing and industry leading IT Staffing and Consulting Firm. While with Collabera he was part of the Executive Management Team, supported their managed services business unit and launched Collabera’s stand-alone Direct Hire Practice. This role provided him with extensive experience in direct hire,...