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From Esq. to Owner (Powered by Atticus)

Author: Lawyer with a Life - Jordan Ostroff

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You started your law firm for more freedom, control, income, and flexibility. But somewhere along the way, the business started running you.

From Esq. to Owner is a practical podcast for solo and small firm attorneys who are great at practicing law but are still figuring out how to lead, manage, hire, delegate, market, and grow.

Hosted by Jordan Ostroff, the Hawaiian-shirt-wearing Lawyer with a Life, this show brings practical solutions with a side of candor, humor, and the occasional pop culture reference. Jordan helps attorneys move from carrying everything themselves to owning and leading the firm they’ve always wanted.

Each episode tackles the real challenges attorneys face after opening their own firm: pricing, staffing, intake, marketing, systems, time management, profitability, leadership, and getting out of the day-to-day chaos.

And because Jordan believes the whole point of building a better firm is having a better life, every episode ends with a little off-the-wall fun…a question, a hot take, a dad joke, a pop culture reference, or something completely unrelated to law.

If you feel buried by the business side of your firm and want solutions for building something better, this show is for you.

Powered by Atticus.

Build Your Firm. Get Your Life Back.
106 Episodes
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What if the fastest way to grow your law firm isn't to build it, but to buy it? Hiring attorneys, expanding into new markets, and adding practice areas can take years. Buying an established law firm could give you a head start, but how do you know whether you're making a smart investment or inheriting someone else's problems? In this episode of From Esq. to Owner, Jordan Ostroff sits down with Victoria Collier, founder of Quid Pro Quo, to talk about what attorneys should know before buying or selling a law firm. Victoria shares what makes a firm attractive to buyers, why revenue doesn't tell the whole story, and how staffing, systems, profitability, and even AI can influence what a practice is worth. Whether you're considering buying another firm to accelerate growth or wondering what your own practice might be worth someday, this conversation offers a perspective on building a law firm that's valuable beyond the work you personally do. ---------------- Inside This Episode: How buying another law firm can accelerate growth and expansion What to look for beyond revenue when evaluating an acquisition How systems, staffing, and AI can influence a law firm's value How to build a firm that's attractive to buyers and less dependent on you Why emotions can lead to costly mistakes when buying a law firm ---------------- Supporting Resources Victoria Collier and Quid Pro Quo: https://quidproquolaw.com/author/victoriacollier/ The Art of Buying and Selling Law Firms Facebook group: https://www.facebook.com/groups/1284225722042602/ Smart Lawyers Position to Transition podcast: https://podcasts.apple.com/us/podcast/smart-lawyers-position-to-transition/id1612863990 Atticus Coaching: https://atticusadvantage.com/coaching/ ---------------- Curious about what it takes to move from practicing law to truly owning your law firm? Contact Atticus to learn how our law firm coaching can help solo and small firm attorneys build stronger systems, lead better teams, delegate with confidence, and make smarter decisions about growth. From Esq. to Owner is a podcast for law firm owners who want practical guidance on law firm leadership, hiring, delegation, operations, marketing, profitability, client service, and sustainable growth, so the business supports your life instead of running it. You can also sign up for the Atticus newsletter to get practical insights on how to grow a law firm, strengthen your role as an owner, improve your systems, and build a more focused, profitable, and sustainable practice. https://atticusadvantage.com/newsletter-signup/ ---------------- Timestamps: 00:00 - How Buying a Law Firm Can Accelerate Growth01:12 - Meet Victoria Collier: From Law Firm Owner to M&A Advisor05:11 - Why Law Firm Owners Buy Other Firms08:54 - Acquiring Experienced Attorneys and Staff09:32 - Growing Revenue Through Law Firm Acquisitions10:25 - Expanding into New Practice Areas11:53 - The Risks of Buying a Law Firm13:18 - What Buyers Should Look for in a Law Firm18:16 - Managing the Transition After an Acquisition22:20 - How Systems and Processes Affect Firm Value24:41 - Private Equity and the Future of Law Firm Acquisitions27:00 - How AI Could Impact Law Firm Valuations32:03 - Preparing Your Law Firm for a Successful Exit37:23 - Major Red Flags When Buying a Law Firm40:22 - The Key to Building a Valuable, Sellable Law Firm
Have you ever had a client complain about a case you thought you handled exceptionally well? Or received a negative review that bothered you far more than you'd like to admit? When you've invested so much of yourself into your work, it's hard not to take criticism personally. You can have dozens of satisfied clients, yet somehow the one who's unhappy is the one you can't stop thinking about. In this episode of From Esq. to Owner, Jordan Ostroff gets into one of the more frustrating parts of running a law firm: dealing with unhappy clients, managing expectations, and handling criticism when it feels personal. Drawing from his own experiences, Jordan challenges attorneys to think differently about client complaints, what they mean for your business, and how much power you give them over your time and attention. If you've ever let one difficult client ruin an otherwise good day, you'll want to hear Jordan's perspective. ---------------- Inside This Episode: How to recognize client red flags and unrealistic expectations during intake Why listening before reacting can help resolve client complaints When to address a complaint, make an accommodation, or stand firm How to handle negative online reviews without compromising client confidentiality How to use client feedback to improve your firm's systems and client experience ---------------- Supporting Resources Attorney and Practice Advisor Jordan Ostroff: https://atticusadvantage.com/team/jordan-ostroff/ Book: Mindset by Carol Dweck https://a.co/d/09PvO5W6 Book: One Small Step Can Change Your Life: The Kaizen Way to Success by Dr. Robert Maurer: https://a.co/d/0h3dbO8D Atticus Coaching: https://atticusadvantage.com/coaching/ ---------------- Curious about what it takes to move from practicing law to truly owning your law firm? Contact Atticus to learn how our law firm coaching can help solo and small firm attorneys build stronger systems, lead better teams, delegate with confidence, and make smarter decisions about growth. From Esq. to Owner is a podcast for law firm owners who want practical guidance on law firm leadership, hiring, delegation, operations, marketing, profitability, client service, and sustainable growth, so the business supports your life instead of running it. You can also sign up for the Atticus newsletter to get practical insights on how to grow a law firm, strengthen your role as an owner, improve your systems, and build a more focused, profitable, and sustainable practice. https://atticusadvantage.com/newsletter-signup/ ---------------- Timestamps:00:00 A Negative Review Does Not Make You a Failure01:06 How to Handle Difficult Clients Without Taking It Personally01:42 What Domino’s Can Teach Law Firms About Complaints03:29 The Best Way to Prevent Client Complaints04:08 Red Flags Before You Ever Take the Case05:47 20% of Clients Can Create 80% of Your Problems06:46 The Best Kind of Client Complaint07:35 Respond to Complaints, Don’t React to Them10:18 Is the Client’s Complaint Actually Valid?11:04 Turn Valid Complaints Into Better Systems13:51 What to Do When the Complaint Is Unreasonable16:03 What Happens When the Complaint Becomes a Bad Review17:40 Your Review Response Is Really for Everyone Else19:19 Why a Few Bad Reviews Aren’t Necessarily a Bad Thing24:27 A Bad Review Is a Learning Opportunity, Not a Failure
Your law firm is bringing in more revenue than ever. So why doesn't it feel like you're making more money? You're paying your team, covering expenses, investing in growth, and keeping the cases coming in. On paper, the firm looks successful, but when you check your bank account, you're left wondering where all that money went. In this episode of From Esq. to Owner, Jordan Ostroff sits down with Leah Miller, founder of Firmly Profits, to talk about why growing revenue doesn't always mean growing profits and what law firm owners need to understand about their numbers. Leah breaks down the difference between revenue, profit, and cash flow, why your bank balance doesn't tell the whole story, and how understanding your financial reports can help you make smarter decisions about hiring, spending, and growing your firm. You don't need to become an accountant to run a profitable law firm, but you do need to know what your numbers are telling you. If your firm is busy, revenue is growing, and you're still asking "Where is all the money going?", this conversation is for you. ---------------- Inside This Episode: Why growing revenue doesn't always mean making more money What your financial statements reveal about your law firm's health How to know when your firm can afford its next hire How to use your numbers to make smarter spending and growth decisions Why paying yourself consistently and building cash reserves matter ---------------- Supporting Resources Leah Miller on Linkedin: https://www.linkedin.com/in/leahlnmfinancial/ Firmly Profits: www.firmlyprofits.com Book: Scaling Up by Verne Harnish: https://a.co/d/07xzNyG0 Atticus Coaching: https://atticusadvantage.com/coaching/ ---------------- Curious about what it takes to move from practicing law to truly owning your law firm? Contact Atticus to learn how our law firm coaching can help solo and small firm attorneys build stronger systems, lead better teams, delegate with confidence, and make smarter decisions about growth. From Esq. to Owner is a podcast for law firm owners who want practical guidance on law firm leadership, hiring, delegation, operations, marketing, profitability, client service, and sustainable growth, so the business supports your life instead of running it. You can also sign up for the Atticus newsletter to get practical insights on how to grow a law firm, strengthen your role as an owner, improve your systems, and build a more focused, profitable, and sustainable practice. https://atticusadvantage.com/newsletter-signup/ ---------------- Timestamps:00:00 The Million-Dollar Cash Flow Problem01:11 Meet Leah Miller: Law Firm Finance 10103:20 Why You Should Outsource Your Bookkeeping04:14 Setting Up Your Accounting Systems and Processes07:25 The Three Financial Reports Every Law Firm Needs09:48 Why Growing Revenue Doesn't Always Mean More Cash11:48 Understanding Your P&L: Revenue, Payroll, and Expenses14:40 Tracking Financial Trends and Planning Ahead16:46 What Profit Really Means for Law Firm Owners21:05 Paying Yourself and Making Profitable Decisions23:14 Calculating Your Law Firm's Break-Even Point24:33 How Hiring Staff Can Actually Increase Profit28:06 Understanding Your Numbers Without Being an Accountant29:51 Building a 3-to-6-Month Financial Safety Net36:13 How to Know Your Financial Strategy Is Working
“There are no great candidates” can feel like the obvious explanation when your law firm keeps struggling to hire or retain good people. But if employees repeatedly leave, new hires never get properly trained, or every search starts after your team is already overwhelmed, the candidate pool may not be the only problem.In this episode of From Esq. to Owner, Aaron Rothert puts Jordan Ostroff in the interview seat and asks him what law firm owners should examine before blaming the hiring market. They discuss how to identify the role your firm actually needs, why hiring too late can undermine a new employee from day one, how to cast a wider net for candidates, and why onboarding and training are just as important as finding the right person.The right hire at the right time can create capacity, support growth, and give a law firm owner more freedom. Listen to learn how to build a hiring process that gives good people a better chance to become great team members.----------------Inside This Episode:How to identify the right hireWhy hiring before your team reaches full capacity mattersWhat separates finding the right person from creating a good employeeA practical way to evaluate the cost of hiringHow to widen your candidate search----------------Supporting ResourcesAaron Rothert, Attorney and Practice Advisor: https://atticusadvantage.com/team/aaron-rothert/DISC Assessment: https://atticusadvantage.com/disc-assessment/Build My Great Team: https://buildmygreatteam.com/Previous Episode: Want to Grow Your Firm? Fix These 5 Things First: https://atticusadvantage.com/podcast/law-firm-growth-strategy/New Hire Onboarding Guide: https://atticusadvantage.com/worksheets/new-hire-onboarding-guide/Atticus Coaching: https://atticusadvantage.com/coaching/----------------Curious about what it takes to move from practicing law to truly owning your law firm? Contact Atticus to learn how our law firm coaching can help solo and small firm attorneys build stronger systems, lead better teams, delegate with confidence, and make smarter decisions about growth. From Esq. to Owner is a podcast for law firm owners who want practical guidance on law firm leadership, hiring, delegation, operations, marketing, profitability, client service, and sustainable growth, so the business supports your life instead of running it.You can also sign up for the Atticus newsletter to get practical insights on how to grow a law firm, strengthen your role as an owner, improve your systems, and build a more focused, profitable, and sustainable practice.https://atticusadvantage.com/newsletter-signup/----------------Timestamps:00:00 – Finding the Right Person for Your Law Firm01:13 – What Hiring Should Actually Accomplish03:00 – The Hidden Cost of Not Hiring04:03 – Identifying the Right Role to Fill05:49 – Using DISC Assessments to Hire Smarter09:08 – Why Law Firms Struggle to Find Great Candidates10:50 – Building a Better Hiring Process12:19 – When Is the Right Time to Hire?14:55 – Creating a 30-60-90 Day Onboarding Plan17:11 – Learning From Hiring Mistakes18:09 – Making New Employees Feel Welcome22:05 – Where to Find Qualified Candidates25:24 – How to Know If You Can Afford to Hire28:11 – Hiring Locally vs. Outsourcing Overseas30:21 – Why the Right Hire Changes Everything
AI can help you get more done. But what are you doing with all that extra capacity? When AI helps you research, create marketing, communicate, and move through your to-do list faster, it's tempting to fill that newly available time with...more work.In this episode of From Esq. to Owner, Jordan Ostroff sits down with Attorney Carolyn Elefant to talk about a bigger opportunity: using AI to help build a law firm that operates more like a business and depends less on the owner doing everything.They discuss where AI can support better systems and delegation, how technology is changing what it takes to start and grow a firm, and why the processes you build can become valuable assets in the business. They also get into an important question every law firm owner using AI eventually has to answer: when should technology handle the work, and when do you still need a human?And because using AI responsibly matters just as much as using it efficiently, Jordan and Carolyn tackle confidentiality, ethics, and some of the risks that come with bringing these tools into your practice.Because the goal isn’t to use AI to cram more work into your day. It’s to use that capacity to build a better law firm.----------------Inside This Episode:Why getting more done with AI doesn’t necessarily mean building a better firmHow AI can support stronger systems and better delegationWhy your processes can become valuable business assetsWhen AI makes sense and when you still need human expertiseWhat law firm owners need to consider about confidentiality, ethics, and responsible AI use----------------Supporting ResourcesCarolyn Elefant LinkedIn: https://www.linkedin.com/in/carolynelefant/MyShingle: https://www.myshingle.com/Book: Four Thousand Weeks by Oliver Burkeman: https://www.oliverburkeman.com/booksThe Summit: https://atticussummit.com/----------------Curious about what it takes to move from practicing law to truly owning your law firm? Contact Atticus to learn how our law firm coaching can help solo and small firm attorneys build stronger systems, lead better teams, delegate with confidence, and make smarter decisions about growth. From Esq. to Owner is a podcast for law firm owners who want practical guidance on law firm leadership, hiring, delegation, operations, marketing, profitability, client service, and sustainable growth, so the business supports your life instead of running it.You can also sign up for the Atticus newsletter to get practical insights on how to grow a law firm, strengthen your role as an owner, improve your systems, and build a more focused, profitable, and sustainable practice.https://atticusadvantage.com/newsletter-signup/----------------Timestamps:00:00 - You Can’t Put the AI Genie Back in the Bottle01:07 - Building an AI-Native Law Firm From Day One01:45 - How Much of Starting a Firm Can AI Actually Do?05:14 - The Advantage of Starting Fresh With AI07:00 - How AI Changes the Way You Think and Work09:08 - Do We Actually Need to Be Less Productive?14:38 - Using AI to Lower Startup Costs17:07 - From Self-Employed Lawyer to Business Owner19:02 - How Your Goals Change When You Own a Business22:09 - Can AI Make You a Better Delegator?26:49 - AI Can Become an Asset of Your Business28:22 - Using AI Responsibly: Ethics and Privacy33:49 - Should Lawyers Tell Clients They Use AI?36:00 - Could NOT Using AI Eventually Be Unethical?39:50 - Carolyn’s Biggest Advice for Lawyers
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