Private Equity Director: The red flags that make investors walk away

Private Equity Director: The red flags that make investors walk away

Most founders think about private equity when they're ready to exit. The reality is, understanding how investors think about valuation, risk, and growth could transform how you build your business today, even if you never plan to sell. Katrina Engelbert is a Director at Pemba Capital Partners, a private equity firm with $2 billion in funds under management and investments across 36 companies. She sits on the board of five portfolio companies and has spent years evaluating businesses, structuring deals, and working alongside founders through the most critical stages of growth. In this conversation, Katrina shares what actually happens when a business gets evaluated by private equity, why the gap between founder optimism and investor skepticism creates friction, and what the bar looks like for businesses that want to attract serious capital. She also explains how AI is reshaping the landscape, why services businesses are suddenly being valued like software companies, and what founders need to know before they ever take a meeting with an investor. She explains: * Why founders and investors see the same business through completely different lenses * The revenue and profitability thresholds that make a business interesting to private equity * What actually gets priced into a valuation, and what doesn't * The red flags that make investors walk away, even when the numbers look good * How AI is changing deal flow, and why services businesses with automation potential are suddenly commanding software multiples * Why liquidity preferences and earn outs exist, and when they actually make sense * What changes when an investor comes on board, and why accountability lifts performance * The reverse due diligence every founder should do before accepting capital * Why every business owner should map out their strategy as if an exit is coming, even if they never plan to sell If you've ever wondered what private equity actually looks for, or whether your business is on the right trajectory to attract serious capital, this episode will give you the investor perspective most founders never get to hear. Timestamps: CHAPTERS * 00:00:00 Introduction * 00:02:02 The Valuation Gap: Why Founders Feel Offended by PE Offers * 00:04:20 Red Flags That Make PE Walk Away Immediately * 00:06:03 Does Culture Actually Impact Valuation? * 00:09:39 What Gets PE Really Excited About a Business * 00:12:18 The AI Revolution: How It's Changing Private Equity * 00:15:31 Services Businesses Trading Like Software: The AI Opportunity * 00:18:35 Red Flags Revisited: Defensiveness and Unrealistic Forecasts * 00:20:47 Due Diligence Explained: What Founders Need to Know * 00:23:52 When PE Comes In: Revenue and Profitability Thresholds * 00:25:51 The Teenage Years: Why PE Targets This Growth Stage * 00:28:43 How PE Finds Deals and Why Inbound Inquiries Are Often Struggling * 00:30:12 Reverse Due Diligence: What Founders Should Ask PE Funds * 00:33:30 The Advisor Problem: When Your Lawyer Isn't M&A Ready * 00:34:50 Liquidity Preferences Explained: Downside Protection or Trap? * 00:37:56 Earn Outs vs. Management Ratchets: Aligning Incentives * 00:39:30 Life After Investment: How Everything Changes * 00:41:03 Rolling Equity: You Don't Have to Exit 100% We're just getting started! Subscribe for more conversations with founders, operators, and their advisers. Katrina Engelbert: LinkedIn https://au.linkedin.com/in/katrinaengelbert [https://au.linkedin.com/in/katrinaengelbert] Pemba Capital Partners https://www.pemba.com.au [https://www.pemba.com.au] At The Top Youtube: https://www.youtube.com/@atthetopwithben [https://www.youtube.com/@atthetopwithben] Instagram: https://www.instagram.com/atthetopwithben/ [https://www.instagram.com/atthetopwithben/] LinkedIn: https://www.linkedin.com/company/at-the-top-with-ben/ [https://www.linkedin.com/company/at-the-top-with-ben/] Spotify: http://open.spotify.com/show/1GTjCXqdQzQtZ33idMpQgo?si=C5gNvXDZSkWdxBz-mW13AA [http://open.spotify.com/show/1GTjCXqdQzQtZ33idMpQgo?si=C5gNvXDZSkWdxBz-mW13AA] Apple Podcasts: http://podcasts.apple.com/us/podcast/at-the-top/id1893782299 [http://podcasts.apple.com/us/podcast/at-the-top/id1893782299]

Cybersecurity Expert: I've had CEOs crying... 'Do I have to sack 500 employees?'

Most business owners think cybersecurity is something they'll deal with later. The reality is, you're already a target, and the threat landscape in 2026 is unlike anything we've seen before. Ahmed Khanji is Founder and CEO of Gridware Cybersecurity, an award winning cybersecurity business. He recently stated that after 17 years in the industry, he's never been more worried. AI powered tools are now finding security vulnerabilities in minutes that used to take teams of PhDs a full year to uncover. Meanwhile, businesses are still operating without basic protections, hoping insurance will save them when things go wrong. In this conversation, Ahmed shares what actually happens when a business gets hacked, why the 10 to 100 employee range is the most vulnerable, and the five essential actions every business owner needs to take right now to avoid becoming another victim on the dark web. He explains: * Why 2026 is the most dangerous year for cybersecurity he's seen in nearly two decades * How businesses actually get hacked, and why it's usually embarrassingly simple * Which businesses are most at risk, and why healthcare tops the list * Why cyber insurance isn't the safety net most business owners think it is * The danger zone for businesses with 10 to 100 employees, and why they're the easiest targets * How AI is being weaponized by threat actors, and what tools like the Mythos model mean for global security * Why building your own software with AI might be exposing your business to catastrophic risk * The uncomfortable truth about your data: it's already out there * Five practical actions you can take in the next few weeks to stop being an easy target If you've been putting off cybersecurity because it feels expensive, complicated, or unlikely to affect you, this episode will change how you think about risk. The question isn't if your business will be targeted. It's when. Timestamps: CHAPTERS * 00:00:00 Introduction * 00:01:42 The AI-Powered Threat: Why 2025 Is Different * 00:05:46 Is This Just Marketing Hype? * 00:08:11 How Businesses Actually Get Hacked * 00:10:52 The Ransomware Nightmare: When CEOs Cry * 00:17:34 The Cat and Mouse Game: Are We Losing? * 00:19:23 The Insurance Trap: Why Coverage Isn't Enough * 00:21:26 Industry Risk Rankings: Who's Most Vulnerable? * 00:29:36 The 10-100 Employee Danger Zone * 00:32:22 The Mythos Model and AI Security Tools * 00:34:09 The Vibe Coding Problem: Building Without Security * 00:37:25 Your Data Is Already Out There * 00:42:16 Five Essential Actions to Protect Your Business * 00:46:48 Closing Thoughts and Resources We're just getting started! Subscribe for more conversations with founders, operators, and their advisers. Ahmed Khanji: LinkedIn https://www.linkedin.com/in/ahmed-khanji/ [https://www.linkedin.com/in/ahmed-khanji/] Gridware Cybersecurity https://gridware.com.au [https://gridware.com.au] At The Top Youtube: https://www.youtube.com/@atthetopwithben [https://www.youtube.com/@atthetopwithben] Instagram: https://www.instagram.com/atthetopwithben/ [https://www.instagram.com/atthetopwithben/] LinkedIn: https://www.linkedin.com/company/at-the-top-with-ben/ [https://www.linkedin.com/company/at-the-top-with-ben/] Spotify: http://open.spotify.com/show/1GTjCXqdQzQtZ33idMpQgo?si=C5gNvXDZSkWdxBz-mW13AA [http://open.spotify.com/show/1GTjCXqdQzQtZ33idMpQgo?si=C5gNvXDZSkWdxBz-mW13AA] Apple Podcasts: http://podcasts.apple.com/us/podcast/at-the-top/id1893782299 [http://podcasts.apple.com/us/podcast/at-the-top/id1893782299]

I Worked Inside Canva & Atlassian: Here's what top leaders do differently

Most founders think they need to have it all figured out. The truth is, the best leaders are just making it up as they go… and learning to be okay with that. Rhiannon Haart is a leadership consultant who has worked inside some of Australia's fastest-growing companies, including Canva and Atlassian. She's seen what happens when founders scale too fast, hold on too long, and struggle with the gap between what they project and what they're really feeling. In this conversation, she shares what actually separates high-performing businesses from the rest: the obsession, the transparency, the willingness to let go, and the hard calls that founders delay far too long. She explains: * Why the gap between internal reality and external projection is where imposter syndrome takes root * What Melanie Perkins at Canva obsessed over that most founders overlook * The behaviors that serve founders early on but quietly sabotage them as the business grows * How to know when someone on your leadership team isn't right for the role anymore, and why delaying that conversation damages more than just performance * Why saying yes to every good idea is often what kills momentum, not what creates it * The simple diagnostic framework she uses to uncover what's actually broken in a business * How to decide who should be in the room when you're setting strategy, and what makes a strategic planning day actually useful If you're leading a growing business and starting to feel the weight of decisions you're not sure how to make, this episode is a reminder that you don't need to have all the answers. You just need to get better at the fundamentals. Timestamps: CHAPTERS * 00:00:00 Introduction * 00:01:34 The Gap Between External Projection and Internal Reality * 00:04:18 Dealing with Imposter Syndrome as a Leader * 00:06:29 What Top Leaders Do Differently: Obsession and Transparency * 00:12:15 Balancing Obsession with Sustainable Culture * 00:14:42 When Founder Behaviors Stop Working: The Delegation Problem * 00:16:42 The Hardest Conversation: Moving On Early Employees * 00:21:38 Leadership Identity Shifts: Navigating Business Growth * 00:24:02 The Founder Bottleneck: When You're the Problem * 00:31:26 Building the Foundation: Strategy, Structure, and Strategic Planning We're just getting started! Subscribe for more conversations with founders, operators, and their advisers. Follow Rhiannon Haart: LinkedIn - https://www.linkedin.com/in/rhiannonhaart/ [https://www.linkedin.com/in/rhiannonhaart/] Foundry Consulting - https://www.foundryconsulting.com.au [https://www.foundryconsulting.com.au] At The Top Youtube: https://www.youtube.com/@atthetopwithben [https://www.youtube.com/@atthetopwithben] Instagram: https://www.instagram.com/atthetopwithben/ [https://www.instagram.com/atthetopwithben/] LinkedIn: https://www.linkedin.com/company/at-the-top-with-ben/ [https://www.linkedin.com/company/at-the-top-with-ben/] Spotify: http://open.spotify.com/show/1GTjCXqdQzQtZ33idMpQgo?si=C5gNvXDZSkWdxBz-mW13AA [http://open.spotify.com/show/1GTjCXqdQzQtZ33idMpQgo?si=C5gNvXDZSkWdxBz-mW13AA] Apple Podcasts: http://podcasts.apple.com/us/podcast/at-the-top/id1893782299 [http://podcasts.apple.com/us/podcast/at-the-top/id1893782299] Show Notes Jeff Bezos: 'You Have Enough Ideas to Destroy Amazon' - https://youtu.be/x698t2pKgT0?si=zfWwfLAUId_VoMcm&t=145 [https://youtu.be/x698t2pKgT0?si=8DGS2y5ndzDml84f&t=145] Mike Cannon-Brooks ‘TEDx Imposter Syndrome’ - https://www.youtube.com/watch?v=zNBmHXS3A6I [https://www.youtube.com/watch?v=zNBmHXS3A6I] Cliftons Strengths / Myers Briggs - https://personality.co/strengths-finder-test [https://personality.co/strengths-finder-test?gclid=Cj0KCQjw_b_QBhCSARIsAP6hR4f1uM9Kp5Y596CQE9ur2fQg6bjpIlQPT09JgQY1EqSyGczfTfij6TIaApmFEALw_wcB&utm_source=google&utm_medium=cpc&utm_campaign=23296896425&utm_content=187856925494&utm_term=cliftonstrengths&matchtype=e&device=c&gad_source=1&gad_campaignid=23296896425&gbraid=0AAAABCDT4dzRHStj5t6qxYqcTggHQYxAC&gclid=Cj0KCQjw_b_QBhCSARIsAP6hR4f1uM9Kp5Y596CQE9ur2fQg6bjpIlQPT09JgQY1EqSyGczfTfij6TIaApmFEALw_wcB] Marlee - https://getmarlee.com/ [https://getmarlee.com/]

I Started My Firm at 25… From a Hospital Bed

Most lawyers dream of making partner. Chris Athanassios walked away from a top-tier firm at the age of 25 to start his own… they told him it was career suicide. Chris is Managing Principal at MillerPrince, a multi-partner law firm he co-founded at an age when most lawyers are still grinding toward their first promotion. In this conversation, he shares what it actually takes to build a firm from scratch: the survival mode, the self-doubt, the moments when credibility mattered more than capability, and the lessons he wishes someone had told him before he signed that first lease. He explains: * Why he knew within six weeks of joining a top-tier firm that he wouldn't stay * How starting young with nothing to lose became his biggest advantage * The six to nine months he went without a salary just to keep the lights on * How publishing a book at 24 helped him overcome age bias and build credibility fast * What happened when one of the founding partners left, and how they stayed friends * How AI is changing the role of junior lawyers and what business owners should use it for * The one question anyone thinking about starting a law firm today needs to answer first If you've ever wondered whether it's too late to start your own firm, or whether now is actually the best time, this episode will challenge how you think about risk, timing, and what it really means to build something of your own. Timestamps: CHAPTERS * 00:00:00 Introduction * 00:01:16 Realizing Big Law Wasn't the Path: Six Weeks to Clarity * 00:03:35 The Decision to Start a Firm: From Rejection to Reality * 00:04:27 Nothing to Lose: The Young Entrepreneur's Advantage * 00:06:02 Overcoming Age Bias: Building Credibility at 25 * 00:06:24 Starting with One Client: The Hospital Bed Launch * 00:08:42 Survival Mode: Six to Nine Months Without Salary * 00:15:55 Growing Into Capability: Taking on Work Before You're Ready * 00:18:02 Business Divorce Done Right: When a Founder Leaves * 00:20:02 Strategic Alignment: Leading a Multi-Partner Firm * 00:21:28 AI and the Future of Legal Services: What Can't Technology Do? * 00:26:49 Should You Start a Law Firm Today? The Key Question Nobody Asks We're just getting started! Subscribe for more conversations with founders, operators, and their advisers. Chris Athanassios: LinkedIn - https://www.linkedin.com/in/christopher-athanassios-5023666a/ [https://www.linkedin.com/in/christopher-athanassios-5023666a/] MillerPrince - https://www.millerprince.com.au/ [https://www.millerprince.com.au/] At The Top Youtube: https://www.youtube.com/@atthetopwithben [https://www.youtube.com/@atthetopwithben] Instagram: https://www.instagram.com/atthetopwithben/ [https://www.instagram.com/atthetopwithben/] LinkedIn: https://www.linkedin.com/company/at-the-top-with-ben/ [https://www.linkedin.com/company/at-the-top-with-ben/] Spotify: http://open.spotify.com/show/1GTjCXqdQzQtZ33idMpQgo?si=C5gNvXDZSkWdxBz-mW13AA [http://open.spotify.com/show/1GTjCXqdQzQtZ33idMpQgo?si=C5gNvXDZSkWdxBz-mW13AA] Apple Podcasts: http://podcasts.apple.com/us/podcast/at-the-top/id1893782299 [http://podcasts.apple.com/us/podcast/at-the-top/id1893782299]

Law Founder: We disrupted ourselves with AI... and doubled revenue with half the team

AI is changing how legal work gets done. But most law firms are watching from the sidelines. Alex Solo saw it coming and made a choice: disrupt his own business before someone else did. Alex is co-founder and CEO of Sprint Law, an award-winning law firm that launched Taylor AI, the world's first voice-enabled AI lawyer for small businesses. In 2022, while his firm was winning awards and scaling fast, he and his co-founder asked a dangerous question: what if we could disrupt ourselves? The result? A complete strategic pivot that doubled revenue with half the team. In this conversation, Alex shares what that journey looked like from the inside, the fears, the framing, the execution, and the lessons learned from betting on technology while everyone else hesitated. He explains: * Why a successful, award-winning law firm decided to disrupt itself in 2022 * How Sprint Law doubled revenue while shrinking the team from 60 to 31 people * What business owners should stop paying lawyers for in the age of AI * The risk matrix framework for deciding when to use AI versus when to hire a lawyer * How to frame major strategic pivots to your team without creating panic * Whether it's too late for small law firms to adopt AI and compete If you're thinking about how AI might reshape your industry, or wondering whether to disrupt your own business model before someone else does, this episode offers a rare look at what that decision looks like in practice, from someone who's living it. Timestamps: CHAPTERS * 00:00:00 Introduction * 00:01:14 The Decision to Disrupt Ourselves * 00:03:25 The Sprint Philosophy: Constant Innovation * 00:04:54 The AI Awakening: ChatGPT Changes Everything * 00:06:44 Big Law vs. Small Firms: Who Will Survive AI? * 00:10:53 Introducing Taylor AI: The Voice-Enabled Lawyer * 00:16:50 What Business Owners Should Stop Paying Lawyers For * 00:18:41 Shrinking the Team, Doubling Revenue * 00:22:24 Announcing the Pivot: Managing Team Fear and Excitement * 00:26:43 Is It Too Late for Small Law Firms? * 00:36:38 The Secret Sauce: Operations Over Legal Tech * 00:39:11 AI Tips and Closing Thoughts We're just getting started! Subscribe for more conversations with founders, operators, and their advisers. Alex Solo: LinkedIn - https://www.linkedin.com/in/asolo/ [https://www.linkedin.com/in/asolo/] Sprint Law: Web - https://sprintlaw.com.au/ [https://sprintlaw.com.au/] LinkedIn - https://www.linkedin.com/company/sprintlaw/ [https://www.linkedin.com/company/sprintlaw/posts/?feedView=all] Instagram - https://www.instagram.com/sprintlaw/ [https://www.instagram.com/sprintlaw/] At The Top Youtube: https://www.youtube.com/@atthetopwithben [https://www.youtube.com/@atthetopwithben] Instagram: https://www.instagram.com/atthetopwithben/ [https://www.instagram.com/atthetopwithben/] LinkedIn: https://www.linkedin.com/company/at-the-top-with-ben/ [https://www.linkedin.com/company/at-the-top-with-ben/] Spotify: http://open.spotify.com/show/1GTjCXqdQzQtZ33idMpQgo? [http://open.spotify.com/show/1GTjCXqdQzQtZ33idMpQgo?si=C5gNvXDZSkWdxBz-mW13AA] Apple Podcasts: http://podcasts.apple.com/us/podcast/at-the-top/id1893782299 [http://podcasts.apple.com/us/podcast/at-the-top/id1893782299]