Small Business Law & Estate Planning Attorney ~ I Help People and Businesses Protect their Legacies through Planning

I help families and small business owners protect their legacy and avoid costly legal pitfalls with clear, customized estate planning and business law solutions.

Many of my clients feel overwhelmed at the thought of “getting their affairs in order.” The legal jargon, the complexity, the time commitment; it all feels intimidating. I get it. That’s why I focus on making legal planning simple, efficient, and tailored to your real needs, not a stack of unnecessary documents you don’t understand.

Whether you're looking to create your first will, update your estate plan, or ensure your business is legally secure, I work with you at your pace to develop a plan that works for your life, not the law firm's billable hours.

One client put it this way:

“Andrew is a fantastic attorney. He was empathetic, deliberate, and professional—always quick to respond and extremely knowledgeable. He helped us navigate a stressful situation with clarity and confidence.”

I founded my firm to bring a more personal, transparent approach to legal services. No pressure. No sales pitch. Just smart, practical advice that protects what matters most to you—your family, your business, and your future.

Ready to take the next step? Schedule a Legal Strategy Session or download free planning tools at www.AndrewMAyers.com.

Andrew Ayers

The question that tells me a client isn't ready...

I declined a client last week. Here's the red flag that made me say no.

She wanted to start an LLC for her consulting business. Had a growing client list. Real revenue. Legitimate need for liability protection.

Then she asked: "What's the cheapest way to do this? I found a site that does it for $49."

I put my pen down.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘩𝘦𝘢𝘳𝘥 𝘵𝘩𝘪𝘴 𝘣𝘦𝘧𝘰𝘳𝘦. 𝘔𝘰𝘳𝘦 𝘵𝘩𝘢𝘯 𝘐'𝘥 𝘭𝘪𝘬𝘦.)

I explained exactly what that $49 gets you:

→ A filing with the state
→ Maybe an EIN
→ No operating agreement
→ No guidance on maintaining corporate formalities
→ A piece of paper that won't protect you when someone sues

She nodded. Said she understood. Then asked if I could just do the filing part and skip the rest.

I told her I couldn't help her.

𝗪𝗵𝘆 𝗧𝗵𝗶𝘀 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻 𝗘𝗻𝗱𝘀 𝘁𝗵𝗲 𝗖𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻:

→ It tells me they want the appearance of protection, not actual protection
→ It signals they'll skip the operating agreement, the separate bank account, the meeting minutes
→ It means they'll mix personal and business expenses because "it's easier"
→ It guarantees I'll see them again after a judge pierces their corporate veil

I've watched this play out. Client files online. Skips the formalities. Gets sued three years later. Opposing counsel goes straight for personal assets. Judge agrees in ten minutes.

The $49 they saved? It cost them everything they were trying to protect.

𝗪𝗵𝗮𝘁 𝗜 𝗧𝗲𝗹𝗹 𝗣𝗲𝗼𝗽𝗹𝗲 𝗪𝗵𝗼 𝗔𝘀𝗸 𝗧𝗵𝗶𝘀:

→ An LLC isn't a purchase. It's a commitment.
→ The state will happily take your filing fee without telling you what you're missing
→ Cheap setup usually means expensive problems
→ Come back when you're ready to do it right

Some attorneys will take that $49 client and upsell them later. I won't.

Because the client who's shopping for the cheapest option isn't looking for protection.

They're looking for a checkbox.

And checkboxes don't hold up in court.

Want my "Starting Your LLC: The First 4 Steps to Get it Right" checklist? DM me and I'll send it over.

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Estate Planning & Small Business Lawyer | Plain-English Legal Planning for Families & Founders | Wills • Trusts • LLCs

When AI plays lawyer

I asked ChatGPT to draft an operating agreement for a two-member LLC. Took about 30 seconds. Looked professional (but a bit shorter than I anticipated). Even had the tell-tale AI formatting.

Then I read it as opposing counsel would.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘴𝘦𝘦𝘯 𝘵𝘩𝘦𝘴𝘦 𝘈𝘐-𝘨𝘦𝘯𝘦𝘳𝘢𝘵𝘦𝘥 𝘥𝘰𝘤𝘶𝘮𝘦𝘯𝘵𝘴 𝘪𝘯 𝘮𝘺 𝘰𝘧𝘧𝘪𝘤𝘦. 𝘔𝘰𝘳𝘦 𝘵𝘩𝘢𝘯 𝘐'𝘥 𝘭𝘪𝘬𝘦.)

𝗪𝗵𝗮𝘁 𝘁𝗵𝗲 𝗔𝗜 𝗚𝗼𝘁 𝗪𝗿𝗼𝗻𝗴:

→ 𝗗𝗲𝗮𝗱𝗹𝗼𝗰𝗸 𝗽𝗿𝗼𝘃𝗶𝘀𝗶𝗼𝗻: "Members shall negotiate in good faith." That's not a provision. That's a hope. What happens when good faith runs out and you're stuck 50/50? The AI didn't say.

→ 𝗩𝗮𝗹𝘂𝗮𝘁𝗶𝗼𝗻 𝗺𝗲𝘁𝗵𝗼𝗱: "Fair market value as determined by a qualified appraiser." Which appraiser? Whose appraiser? What methodology? I've seen partners spend $40,000 fighting over what "fair market value" means because nobody defined it upfront.

→ 𝗗𝗶𝘀𝘁𝗿𝗶𝗯𝘂𝘁𝗶𝗼𝗻 𝗰𝗹𝗮𝘂𝘀𝗲𝘀: The AI gave me boilerplate about "distributions at the discretion of the members." Discretion becomes a weapon when one partner wants cash, and the other wants to reinvest.

→ 𝗕𝘂𝘆𝗼𝘂𝘁 𝘁𝗿𝗶𝗴𝗴𝗲𝗿𝘀: Nothing about death, disability, divorce, or deadlock. Nothing about what happens when one partner wants out, and the other doesn't. Just silence where the hard questions should be.

The document looked complete. It wasn't.

𝗪𝗵𝘆 𝗧𝗵𝗶𝘀 𝗠𝗮𝘁𝘁𝗲𝗿𝘀:

AI is trained on thousands of operating agreements. It knows what they look like. It doesn't know what yours needs to say.

It can't ask about your partner's risk tolerance. It doesn't know your spouse might have community property claims. It won't push back when you say "we'll figure it out."

I have a case going to trial because two partners had an operating agreement that looked professional but said nothing about what happens when they disagree.

𝗪𝗵𝗮𝘁 𝗔𝗜 𝗖𝗮𝗻'𝘁 𝗗𝗼:

→ Ask the uncomfortable questions before you need answers
→ Anticipate the fight you don't see coming
→ Know which generic clause will fail in your state
→ Push back when you're making a mistake

AI can draft a document in 30 seconds.

It just can't tell you whether it'll hold up in court.

And by the time you find out, you're paying for both attorneys.

The 50/50 partnership killer

Two business partners came to me in 2024. Best friends since college. Started a marketing agency together. Split everything 50/50.

"We agree on everything," they told me.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘩𝘦𝘢𝘳𝘥 𝘵𝘩𝘪𝘴 𝘣𝘦𝘧𝘰𝘳𝘦. 𝘌𝘷𝘦𝘳𝘺 𝘱𝘢𝘳𝘵𝘯𝘦𝘳𝘴𝘩𝘪𝘱 𝘢𝘨𝘳𝘦𝘦𝘴 𝘰𝘯 𝘦𝘷𝘦𝘳𝘺𝘵𝘩𝘪𝘯𝘨. 𝘜𝘯𝘵𝘪𝘭 𝘵𝘩𝘦𝘺 𝘥𝘰𝘯'𝘵.)

I asked them one question: "What happens when you disagree?"

They looked at each other. Shrugged. "We'll figure it out."

Their operating agreement? Downloaded from the internet. No deadlock provision. No tie-breaker mechanism. No buyout process.

I gave them my recommendations. They chose to leave them for another day.

Eight months later, one partner wanted to hire a sales director. The other wanted to invest in new software. They couldn't afford both.

One vote for hiring. One vote for software.

50/50. Complete standstill.

Both scheduled meetings with me separately. I told them both I can't get involved.

𝗪𝗵𝗮𝘁 𝗧𝗵𝗲 𝗠𝗶𝘀𝘀𝗶𝗻𝗴 𝗖𝗹𝗮𝘂𝘀𝗲 𝗖𝗼𝘀𝘁 𝗧𝗵𝗲𝗺:

→ Six months of paralysis while competitors moved
→ $40,000 in legal fees trying to unwind the partnership
→ A friendship that ended in a mediation room
→ A business that sold for half its value because neither could buy the other out

The clause that was missing? A deadlock resolution provision. Three sentences that would have cost them $500 to draft.

𝗪𝗵𝗮𝘁 𝗘𝘃𝗲𝗿𝘆 𝟱𝟬/𝟱𝟬 𝗣𝗮𝗿𝘁𝗻𝗲𝗿𝘀𝗵𝗶𝗽 𝗡𝗲𝗲𝗱𝘀:

→ Deadlock provision: What happens when you can't agree
→ Tie-breaker mechanism: Third-party mediator, rotating authority, or coin flip
→ Buyout trigger: How either partner can exit without destroying the business
→ Valuation method: Agreed-upon formula before emotions run high

Equal ownership doesn't require equal paralysis.

The partnerships that survive? They plan for disagreement before they disagree. They build the exit door while they still like each other.

Your partner might be different.

But math isn't. One vote plus one vote equals zero decisions.

And no amount of friendship survives a six-month standstill.

The LLC dissolution headed to trial

I have a case going to trial at the end of April. Two partners. Had a business together. Never had an operating agreement.

My client said to me last week: "This has taken forever."

I had to tell him: "It hasn't even been two years."

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘩𝘢𝘥 𝘵𝘩𝘪𝘴 𝘤𝘰𝘯𝘷𝘦𝘳𝘴𝘢𝘵𝘪𝘰𝘯 𝘣𝘦𝘧𝘰𝘳𝘦. 𝘍𝘰𝘳 𝘤𝘰𝘯𝘵𝘦𝘴𝘵𝘦𝘥 𝘭𝘪𝘵𝘪𝘨𝘢𝘵𝘪𝘰𝘯, 𝘵𝘸𝘰 𝘺𝘦𝘢𝘳𝘴 𝘪𝘴 𝘢𝘤𝘵𝘶𝘢𝘭𝘭𝘺 𝘧𝘢𝘴𝘵.)

When the partnership went sideways, there was nothing to guide the exit. No buyout process. No valuation method. No deadlock provision. Just two people who used to be friends, now fighting over how to unwind something they never properly built.

We went to mediation. My client has real damages. The other partner just wants it dissolved without paying anything.

Their offer? "You pay us fifty thousand, and we'll walk away."

That's what it costs my client to go to trial.

𝗪𝗵𝗮𝘁 𝗧𝗵𝗲 𝗠𝗶𝘀𝘀𝗶𝗻𝗴 𝗢𝗽𝗲𝗿𝗮𝘁𝗶𝗻𝗴 𝗔𝗴𝗿𝗲𝗲𝗺𝗲𝗻𝘁 𝗖𝗼𝘀𝘁:

→ Two years of litigation instead of a clean exit
→ Legal fees that could have funded the next business
→ A trial date with no resolution in sight
→ Two former partners who now communicate through attorneys

The operating agreement they skipped? Would have cost them a bit of money and a couple hours of uncomfortable conversation.

𝗪𝗵𝗮𝘁 𝗘𝘃𝗲𝗿𝘆 𝗣𝗮𝗿𝘁𝗻𝗲𝗿𝘀𝗵𝗶𝗽 𝗡𝗲𝗲𝗱𝘀 𝗕𝗲𝗳𝗼𝗿𝗲 𝗗𝗮𝘆 𝗢𝗻𝗲:

→ Buyout trigger: How either partner can exit
→ Valuation method: Agreed-upon formula before emotions run high
→ Deadlock provision: What happens when you can't agree
→ Dissolution process: How to unwind without a courtroom

The partners who avoid this? They have the hard conversation when they still like each other. They build the exit door before they need it.

Your business partner might be different.

But two years of litigation looks the same for everyone.

And no amount of optimism survives a trial date.

"The minute my wife was pregnant, I knew I needed this."

I was at our INC Group meeting yesterday when Jeremy James dropped a great way to look at estate planning.

He's in the real estate industry and deals with five to eight probates a month. Sees families torn apart by poor planning constantly.

But he wasn't talking about his clients. He was talking about himself.

"I'll sleep way better at night," he said. "Once you get over that conversation of 'yeah, we're all going to die someday,' you realize—if it happens tomorrow, everyone's taken care of."

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘩𝘦𝘢𝘳𝘥 𝘵𝘩𝘪𝘴 𝘣𝘦𝘧𝘰𝘳𝘦. 𝘌𝘷𝘦𝘳𝘺𝘰𝘯𝘦 𝘱𝘢𝘯𝘪𝘤𝘴 𝘢𝘣𝘰𝘶𝘵 𝘵𝘩𝘪𝘯𝘬𝘪𝘯𝘨 𝘢𝘣𝘰𝘶𝘵 𝘪𝘵. 𝘜𝘯𝘵𝘪𝘭 𝘵𝘩𝘦𝘺 𝘧𝘪𝘯𝘢𝘭𝘭𝘺 𝘥𝘰 𝘪𝘵.)

Here's what most people don't realize about estate planning:

The hardest part isn't the documents. It's having the conversation with yourself.

Admitting mortality. Thinking through the what-ifs. Facing the uncomfortable reality that life doesn't wait for convenient timing.

But once you push through that discomfort? Relief.

Not anxiety. Not dread. Just the quiet confidence that comes from knowing your family is protected.

𝗪𝗵𝗮𝘁 𝗣𝗲𝗮𝗰𝗲 𝗼𝗳 𝗠𝗶𝗻𝗱 𝗔𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗟𝗼𝗼𝗸𝘀 𝗟𝗶𝗸𝗲:

→ Sleeping better because the plan exists
→ Knowing exactly who handles what if something happens
→ No scrambling for documents during a crisis
→ Your family protected, not burdened

And here's something else that may surprise you: your documents don't expire.

I have clients come in with twenty-five-year-old wills that are still valid. If they got hit by a bus on the way out of my office? They were covered. They just have some changes they want to make now.

The investment you make today protects your family for decades.

The conversation everyone avoids? It takes an hour.

The peace of mind that follows? It lasts the rest of your life.

Usually, I'm in the audience for the presentations, but yesterday was my turn to present on some foundational estate planning principles.

If you're in the Twin Cities area and are interested in learning more about our INC Group, shoot me or Tony Rubin a DM.

CEO of The James Gang Real Estate Consultants of Keller Williams Owner and founder of D1 Training Savage

Financial Advisor at Rudin & Rubin Financial Group of Wells Fargo Advisors

The 3 clauses that fail in court

I've rewritten many operating agreements. Most have the same three problems.

These aren't typos. They're ticking time bombs that explode when partners stop getting along.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘴𝘦𝘦𝘯 𝘦𝘢𝘤𝘩 𝘰𝘧 𝘵𝘩𝘦𝘴𝘦 𝘧𝘢𝘪𝘭 𝘪𝘯 𝘳𝘦𝘢𝘭 𝘵𝘪𝘮𝘦.)

𝗖𝗹𝗮𝘂𝘀𝗲 #𝟭: "𝗠𝗲𝗺𝗯𝗲𝗿𝘀 𝘀𝗵𝗮𝗹𝗹 𝗮𝗴𝗿𝗲𝗲 𝗼𝗻 𝗮𝗹𝗹 𝗺𝗮𝗷𝗼𝗿 𝗱𝗲𝗰𝗶𝘀𝗶𝗼𝗻𝘀."

Sounds reasonable. Until they don't agree.

No deadlock provision. No tiebreaker. No path forward. Two 50/50 partners who hate each other, frozen in place. The business dies while they argue.

𝗖𝗹𝗮𝘂𝘀𝗲 #𝟮: "𝗔 𝗺𝗲𝗺𝗯𝗲𝗿 𝗺𝗮𝘆 𝘀𝗲𝗹𝗹 𝘁𝗵𝗲𝗶𝗿 𝗶𝗻𝘁𝗲𝗿𝗲𝘀𝘁 𝗮𝘁 𝗳𝗮𝗶𝗿 𝗺𝗮𝗿𝗸𝗲𝘁 𝘃𝗮𝗹𝘂𝗲."

Fair market value according to whom?

One partner thinks the business is worth $2 million. The other says $500K. Now you're paying two business appraisers to fight in court.

𝗖𝗹𝗮𝘂𝘀𝗲 #𝟯: "𝗗𝗶𝘀𝘁𝗿𝗶𝗯𝘂𝘁𝗶𝗼𝗻𝘀 𝘀𝗵𝗮𝗹𝗹 𝗯𝗲 𝗺𝗮𝗱𝗲 𝗮𝘀 𝗱𝗲𝘁𝗲𝗿𝗺𝗶𝗻𝗲𝗱 𝗯𝘆 𝘁𝗵𝗲 𝗺𝗲𝗺𝗯𝗲𝗿𝘀."

Translation: The partner who controls the checkbook decides when anyone gets paid.

I've seen majority owners starve out minority partners for years. No distributions. No recourse. The minority partner's ownership becomes worthless on paper.

𝗪𝗵𝘆 𝗧𝗵𝗲𝘀𝗲 𝗞𝗲𝗲𝗽 𝗦𝗵𝗼𝘄𝗶𝗻𝗴 𝗨𝗽:

→ Template agreements pulled from the internet
→ Attorneys who don't litigate these disputes
→ Partners who think they'll always get along
→ "We'll figure it out later" mentality

The operating agreements that hold up? They assume the partnership will fail. They build the exit before anyone needs it.

Your business partner might be different.

But vague language reads the same to every judge.

And "we'll work it out" isn't a clause that holds up in court.

The search history that cost a client $200K...

He had been representing himself and came to me mid-divorce (because his friend used me for his divorce back in 2009), and he felt like he was in over his head. But, he said he'd done his research, and he wanted to "get creative" with some business assets before discovery.

I referred him out to a friend of mine, who unfortunately stepped into a wasp's nest of discovery issues.

What the client hadn't paid attention to while representing himself? His wife's attorney had already sent out a variety of subpoenas and retained a computer forensic expert.

The searches they found:

→ "how to hide money from divorce"
→ "can wife find LLC assets"
→ "transfer property to family member divorce"
→ "offshore accounts legal"

He'd Googled his entire strategy before walking into my office.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘴𝘦𝘦𝘯 𝘵𝘩𝘪𝘴 𝘣𝘦𝘧𝘰𝘳𝘦. 𝘗𝘦𝘰𝘱𝘭𝘦 𝘵𝘩𝘪𝘯𝘬 𝘪𝘯𝘤𝘰𝘨𝘯𝘪𝘵𝘰 𝘮𝘰𝘥𝘦 𝘮𝘦𝘢𝘯𝘴 𝘪𝘯𝘷𝘪𝘴𝘪𝘣𝘭𝘦. 𝘐𝘵 𝘥𝘰𝘦𝘴𝘯'𝘵.)

Once the computer data was analyzed, the forensic accountant didn't even need to trace the money. The search history was the roadmap. Every query showed intent. Every timestamp showed premeditation.

The judge saw a man who planned to deceive the court before he ever filed a motion.

𝗪𝗵𝗮𝘁 𝗧𝗵𝗮𝘁 𝗦𝗲𝗮𝗿𝗰𝗵 𝗛𝗶𝘀𝘁𝗼𝗿𝘆 𝗖𝗼𝘀𝘁 𝗛𝗶𝗺:

→ Lost credibility on every financial claim he made
→ Judge awarded wife more than 50% of their assets
→ Sanctioned for discovery abuse
→ Paid the wife's attorneys' fees
→ Extra $200K gone because he thought Google was private

The internet doesn't outsmart forensic accountants. It creates evidence for them.

𝗪𝗵𝗮𝘁 𝗣𝗲𝗼𝗽𝗹𝗲 𝗗𝗼𝗻'𝘁 𝗨𝗻𝗱𝗲𝗿𝘀𝘁𝗮𝗻𝗱 𝗔𝗯𝗼𝘂𝘁 𝗗𝗶𝘀𝗰𝗼𝘃𝗲𝗿𝘆:

→ Browser history is discoverable
→ Deleted searches can be recovered
→ Your phone backs up more than you think
→ "Research" looks like "planning" to a judge

The clients who protect themselves? They don't Google schemes. They hire professionals before there's a problem.

Your search bar isn't a consultation.

It's a confession waiting to be subpoenaed.

And as you probably know already, it's only a matter of time before your chats with an AI are marked as Exhibit A in a trial...

5 questions that DIY website won't ask

I review a lot of estate plans that people tried to DIY. Most have the same problem.

The documents are technically correct. The forms are filled out. Sometimes the signatures are notarized.

But websites don'ts ask the questions that actually matter.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘴𝘦𝘦𝘯 𝘵𝘩𝘦 𝘳𝘦𝘴𝘶𝘭𝘵𝘴 𝘸𝘩𝘦𝘯 𝘵𝘩𝘦𝘺 𝘥𝘰𝘯'𝘵.)

𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻 #𝟭: "𝗛𝗮𝘃𝗲 𝘆𝗼𝘂 𝘁𝗮𝗹𝗸𝗲𝗱 𝘁𝗼 𝘁𝗵𝗲 𝗽𝗲𝗼𝗽𝗹𝗲 𝘆𝗼𝘂'𝗿𝗲 𝗻𝗮𝗺𝗶𝗻𝗴?"

Your personal representative might not want the job. Your healthcare agent might freeze under pressure. Your trustee might have no idea what you expect from them.

Naming someone in a document isn't the same as preparing them.

𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻 #𝟮: "𝗪𝗵𝗮𝘁 𝗵𝗮𝗽𝗽𝗲𝗻𝘀 𝗶𝗳 𝘆𝗼𝘂𝗿 𝗳𝗶𝗿𝘀𝘁 𝗰𝗵𝗼𝗶𝗰𝗲 𝗰𝗮𝗻'𝘁 𝘀𝗲𝗿𝘃𝗲?"

I had a case last summer. Client's mother named her brother as personal representative. He'd had a stroke two years earlier. Couldn't manage his own finances, let alone hers.

No alternate named. Four months of family conflict over who would step in.

𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻 #𝟯: "𝗪𝗵𝗮𝘁 𝗸𝗲𝗲𝗽𝘀 𝘆𝗼𝘂 𝘂𝗽 𝗮𝘁 𝗻𝗶𝗴𝗵𝘁?"

Most families don't need protection from probate court. They need protection from Tuesday afternoon emergencies.

Who makes decisions if both spouses are incapacitated? Who has access to accounts? Where are the documents?

𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻 #𝟰: "𝗗𝗼 𝘆𝗼𝘂𝗿 𝗸𝗶𝗱𝘀 𝗵𝗮𝘃𝗲 𝗱𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁 𝗿𝗲𝗹𝗮𝘁𝗶𝗼𝗻𝘀𝗵𝗶𝗽𝘀 𝘄𝗶𝘁𝗵 𝗺𝗼𝗻𝗲𝘆?"

Equal inheritance doesn't require equal control. The kid who knows the business should run the business. Give the others their share without giving them a vote.

𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻 #𝟱: "𝗪𝗵𝗲𝗻 𝗱𝗶𝗱 𝘆𝗼𝘂 𝗹𝗮𝘀𝘁 𝗿𝗲𝘃𝗶𝗲𝘄 𝘁𝗵𝗶𝘀?"

The personal representative you named five years ago might not be the right choice today. Health changes. Relationships change. People move away.

Your estate plan should keep up.

The attorneys who ask these questions aren't trying to bill more hours.

They're trying to build plans that actually work when families need them.

Because a signed document isn't a plan.

It's just the beginning of one.

The personal representative who couldn't serve

Last summer, a client's mother passed away. She'd named her brother as personal representative of her estate.

One problem: He'd had a stroke two years ago. Couldn't manage his own finances, let alone hers.

The will was ten years old. Back then, he was the obvious choice. Responsible. Local. Knew the family.

Now? He couldn't sign his own name.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘴𝘦𝘦𝘯 𝘵𝘩𝘪𝘴 𝘣𝘦𝘧𝘰𝘳𝘦. 𝘔𝘰𝘳𝘦 𝘵𝘩𝘢𝘯 𝘐'𝘥 𝘭𝘪𝘬𝘦.)

Under Minnesota law, when a named personal representative can't serve, things get complicated fast.

𝗪𝗵𝗮𝘁 𝗛𝗮𝗽𝗽𝗲𝗻𝘀 𝗪𝗵𝗲𝗻 𝗬𝗼𝘂𝗿 𝗣𝗥 𝗖𝗮𝗻'𝘁 𝗦𝗲𝗿𝘃𝗲:

→ If you named an alternate, they step in
→ If you didn't, the court follows a statutory priority list
→ Surviving spouse gets first priority
→ Then adult children
→ Then other heirs
→ If multiple people have equal priority and can't agree, the court decides

My client's family? No alternate named. Three adult children. Two wanted to serve. One didn't trust the other two.

We spent four months sorting out who would administer an estate that should have taken four weeks.

𝗪𝗵𝗮𝘁 𝗧𝗵𝗮𝘁 𝗠𝗶𝘀𝘀𝗶𝗻𝗴 𝗔𝗹𝘁𝗲𝗿𝗻𝗮𝘁𝗲 𝗖𝗼𝘀𝘁:

→ Legal fees that ate into the inheritance
→ Four months of family tension
→ Assets sitting frozen while siblings argued
→ Relationships strained over a problem that didn't need to exist

𝗛𝗼𝘄 𝘁𝗼 𝗣𝗿𝗲𝗽𝗮𝗿𝗲 𝗦𝗼 𝗧𝗵𝗶𝘀 𝗗𝗼𝗲𝘀𝗻'𝘁 𝗛𝗮𝗽𝗽𝗲𝗻:

→ Name at least one alternate personal representative
→ Consider naming two alternates if your first choice is older
→ Review your documents at least every 3 years
→ Have the conversation with your choices before you need them
→ Make sure your alternates actually want the job

The personal representative you named five years ago might not be the right choice today.

Health changes. Relationships change. People move away.

Your estate plan should keep up.

Because the court will happily appoint someone to handle your affairs.

It just might not be who you would have chosen.

The client who did his homework

Had a call this week with a guy looking to move rental properties into LLCs. Before we even got started, he said something I don't hear often:

"I dug through my mortgage documents last night. Found a section about assumptions."

He'd located the exact clause. Read the fine print. Identified that his lender wouldn't allow assumption of the loan on original terms.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘩𝘢𝘥 𝘤𝘭𝘪𝘦𝘯𝘵𝘴 𝘸𝘩𝘰 𝘥𝘪𝘥𝘯'𝘵 𝘬𝘯𝘰𝘸 𝘵𝘩𝘦𝘺 𝘩𝘢𝘥 𝘢 𝘮𝘰𝘳𝘵𝘨𝘢𝘨𝘦 𝘰𝘯 𝘵𝘩𝘦 𝘱𝘳𝘰𝘱𝘦𝘳𝘵𝘺.)

That one clause? It changed our entire strategy for that property. Instead of assuming we could transfer freely, we now knew to call the lender first. Ask permission. Get it in writing.

Most people sign contracts and file them away. They trust that someone else will catch the important stuff later.

𝗪𝗵𝗮𝘁 𝗡𝗼𝘁 𝗥𝗲𝗮𝗱𝗶𝗻𝗴 𝗬𝗼𝘂𝗿 𝗖𝗼𝗻𝘁𝗿𝗮𝗰𝘁𝘀 𝗖𝗮𝗻 𝗖𝗼𝘀𝘁:

→ Due-on-sale clauses triggered unexpectedly
→ Transfer restrictions you didn't know existed
→ Penalties buried in paragraph 47
→ Opportunities missed because you didn't know your options

I work with a mortgage broker who used to say lenders never enforce due-on-sale clauses on LLC transfers. Then last spring, a client's lender sold their mortgage to a private equity-backed company. New lender said no.

The assumption that "it'll be fine" doesn't hold up when ownership changes hands.

𝗪𝗵𝗮𝘁 𝗘𝘃𝗲𝗿𝘆 𝗣𝗿𝗼𝗽𝗲𝗿𝘁𝘆 𝗢𝘸𝗻𝗲𝗿 𝗦𝗵𝗼𝘂𝗹𝗱 𝗗𝗼:

→ Pull out your mortgage documents tonight
→ Search for "transfer," "assumption," and "due on sale"
→ Know what your lender can and can't restrict
→ Call before you act, not after

Your attorney can guide the strategy. But we can't catch what we don't know exists.

The clients who come prepared? They save time, avoid surprises, and make better decisions.

Your contracts aren't just paperwork to file away.

They're the rules of the game you're playing.

Read them before someone else uses them against you.

Why didn't you go back to Steve?

I clean up a lot of estate plans that other attorneys drafted. It's become a regular part of my practice.

When new clients come in, I always ask: "You worked with someone before. Why didn't you go back to them?"

The answers are almost always the same:

"I don't remember who it was."

"I didn't have a good experience."

"They never followed up. I figured they didn't care."

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘩𝘦𝘢𝘳𝘥 𝘵𝘩𝘪𝘴 𝘦𝘯𝘰𝘶𝘨𝘩 𝘵𝘪𝘮𝘦𝘴 𝘵𝘰 𝘴𝘦𝘦 𝘵𝘩𝘦 𝘱𝘢𝘵𝘵𝘦𝘳𝘯.)

The thing is, "Steve" probably thinks his client is still his client. "Steve" has no idea they're sitting in my office saying, "yeah, forget Steve, I'm starting fresh."

𝗪𝗵𝗮𝘁 𝗟𝗼𝘀𝗶𝗻𝗴 𝗧𝗼𝘂𝗰𝗵 𝗔𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗖𝗼𝘀𝘁𝘀:

→ The update they needed three years later
→ The referral they would have made without thinking
→ The trust they built that walked out the door
→ Revenue that went to someone who stayed in touch

Estate planning isn't a one-time transaction. Life changes. Kids grow up. Assets shift. Marriages happen. Divorces happen. The documents need to keep up.

But if your clients can't remember your name, they're not calling you when things change.

𝗪𝗵𝗮𝘁 𝗦𝘁𝗮𝘆𝗶𝗻𝗴 𝗶𝗻 𝗧𝗼𝘂𝗰𝗵 𝗔𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗟𝗼𝗼𝗸𝘀 𝗟𝗶𝗸𝗲:

→ An annual check-in, even just an email
→ Content that reminds them you exist
→ Being the person they think of when something changes
→ Making it easy to come back

I'm not saying this to criticize other attorneys. I'm saying it because I've been on both sides.

The clients who come back? They remember how you made them feel. They remember that you followed up. They remember that you seemed to care about more than the transaction.

The clients who don't come back? They just remember that someone named "Steve" did their will once.

And "Steve" never hears about it.

Your best marketing isn't finding new clients.

It's making sure the ones you have don't forget you exist.

No pilot. No flight.

Our Delta flight got delayed this week. Not because of weather. Not because of mechanical issues.

Because no pilot was scheduled to fly the plane.

We boarded. Sat down. Got comfortable. Then the announcement came: "We need everyone to deplane. There's no pilot assigned to this flight."

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐 𝘸𝘪𝘴𝘩 𝘐 𝘸𝘢𝘴 𝘮𝘢𝘬𝘪𝘯𝘨 𝘵𝘩𝘪𝘴 𝘶𝘱.)

A few hours later, they found someone. We finally took off.

But I kept thinking about it.

𝗪𝗵𝗮𝘁 𝗢𝗻𝗲 𝗠𝗶𝘀𝘀𝗶𝗻𝗴 𝗣𝗶𝗲𝗰𝗲 𝗔𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗖𝗼𝘀𝘁:

→ Hundreds of passengers delayed
→ Missed connections rippling through the system
→ Gate agents scrambling to manage frustrated travelers
→ A multi-billion dollar operation grinding to a halt

Delta has sophisticated scheduling software. Thousands of employees. Decades of operational experience.

And none of it mattered because one line item was missing from a spreadsheet somewhere.

𝗪𝗵𝘆 𝗧𝗵𝗶𝘀 𝗛𝗮𝗽𝗽𝗲𝗻𝘀:

→ Complex systems create blind spots
→ Everyone assumes someone else is checking
→ The basics get overlooked while teams focus on optimization
→ No redundancy for the things that seem "obvious"

I see this in business planning all the time. Clients build elaborate structures but miss the foundational piece that holds everything together. The operating agreement nobody reviewed. The succession plan that assumed everyone would get along. The backup that was never tested.

The plane was ready. The crew was ready. The passengers were ready.

But without the one person who could actually fly it, nothing moved.

Your system is only as strong as the piece you forgot to check.

𝙋.𝙎. 𝙄 𝙘𝙝𝙖𝙡𝙠 𝙩𝙝𝙞𝙨 𝙪𝙥 𝙩𝙤 𝙩𝙝𝙚 𝙛𝙖𝙘𝙩 𝙩𝙝𝙖𝙩, 𝙮𝙚𝙩 𝙖𝙜𝙖𝙞𝙣, 𝙄 𝙙𝙞𝙙𝙣'𝙩 𝙧𝙪𝙣 𝙞𝙣𝙩𝙤 Kristi Paulson 𝙖𝙩 𝙩𝙝𝙚 𝙖𝙞𝙧𝙥𝙤𝙧𝙩...

The hidden cost of free AI tools

Our resident cybersecurity expert Christopher Steffl said something at our INC meeting last week that hit us all pretty hard:

"If it's free, do not use it. Your data is worth far more than your subscription."

He works with small businesses on security. His firm now immediately drops free AI tool use by their clients.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘵𝘩𝘢𝘵 𝘴𝘰𝘶𝘯𝘥𝘴 𝘦𝘹𝘵𝘳𝘦𝘮𝘦. 𝘜𝘯𝘵𝘪𝘭 𝘺𝘰𝘶 𝘶𝘯𝘥𝘦𝘳𝘴𝘵𝘢𝘯𝘥 𝘸𝘩𝘺.)

He told us about a design shop client. Twenty-five years of intellectual property. Proprietary designs. Client information. Trade secrets.

They uploaded all of it into free AI tools because they thought they had to "ride the wave."

That data? Now training models. Potentially searchable. Definitely not private.

𝗪𝗵𝗮𝘁 𝗠𝗼𝘀𝘁 𝗕𝘂𝘀𝗶𝗻𝗲𝘀𝘀𝗲𝘀 𝗗𝗼𝗻'𝘁 𝗥𝗲𝗮𝗹𝗶𝘇𝗲:

→ Free tools need your data to train their models, that's the business model
→ What you upload can be searched by others asking the right questions
→ Your "private" business conversations may not be private at all
→ Employees are dumping sensitive information into ChatGPT with no policies in place

And here's where it gets interesting for my world:

A recent court decision found that what you submit to AI tools isn't protected by attorney-client privilege. Meaning if you're asking ChatGPT legal questions about your business dispute, that conversation could be discoverable in litigation.

Our next round of discovery requests will include: "What does your ChatGPT history show?"

𝗪𝗵𝗮𝘁 𝗬𝗼𝘂 𝗦𝗵𝗼𝘶𝗹𝗱 𝗕𝗲 𝗗𝗼𝗶𝗻𝗴:

→ Pay for the tools you use (the paid versions often have better privacy protections)
→ Never upload confidential client information to free AI
→ Create clear AI policies for your employees
→ Use general terms, don't use real names, real companies, real deal details
→ If you need legal advice, ask your attorney, not an AI

Chris put it simply: "They need the data to train the models. That's why it's free."

Your intellectual property. Your client information. Your competitive advantage.

That's what you're paying with.

The subscription you're avoiding? It's cheaper than what you're giving away.

If you're in the Twin Cities area and are interested in learning more about our INC Group, shoot me or Tony Rubin a DM.

The $40,000 comma.

I mentioned this case in a recent post. Partners fighting over what "fair market value" means because nobody defined it upfront.

Here's the full story.

Two members. 50/50 LLC. Five years of building something together. Then one wanted out.

Their operating agreement said the departing member would be bought out at "fair market value, as determined by a qualified appraiser."

Sounds reasonable. It wasn't.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘴𝘦𝘦𝘯 𝘵𝘩𝘪𝘴 𝘦𝘹𝘢𝘤𝘵 𝘧𝘪𝘨𝘩𝘵 𝘣𝘦𝘧𝘰𝘳𝘦. 𝘔𝘰𝘳𝘦 𝘵𝘩𝘢𝘯 𝘐'𝘥 𝘭𝘪𝘬𝘦.)

𝗪𝗵𝗲𝗿𝗲 𝘁𝗵𝗲 𝗙𝗶𝗴𝗵𝘁 𝗦𝘁𝗮𝗿𝘁𝗲𝗱:

→ Which appraiser? Each partner wanted their own.
→ What methodology? One wanted asset-based. The other wanted income-based. Difference: $180,000.
→ What date? Value as of the exit notice? The actual buyout? Six months earlier when things were better?
→ Minority discount? The agreement didn't say. One side argued yes. The other said no.

The clause was twelve words. The dispute lasted fourteen months.

𝗪𝗵𝗮𝘁 𝗧𝗵𝗮𝘁 𝗔𝗺𝗯𝗶𝗴𝘂𝗶𝘁𝘆 𝗖𝗼𝘀𝘁:

→ $40,000+ in combined legal fees
→ A business that couldn't make decisions while the owners fought
→ Two people who started as friends and ended as opposing parties
→ Fourteen months of uncertainty for employees, vendors, and customers

The buyout that should have taken 60 days took over a year.

𝗪𝗵𝗮𝘁 𝗧𝗵𝗲 𝗖𝗹𝗮𝘂𝘀𝗲 𝗦𝗵𝗼𝘂𝗹𝗱 𝗛𝗮𝘃𝗲 𝗦𝗮𝗶𝗱:

→ Name the valuation method (multiple of EBITDA, book value, third-party appraisal)
→ Specify who selects the appraiser (or use a process: each picks one, those two pick a third)
→ Define the valuation date
→ State whether minority/marketability discounts apply
→ Set a timeline for completion

The partners who avoid this? They answer these questions when they still like each other. When emotions aren't running high. When "fair" is something they can agree on.

Your operating agreement might have the same twelve words theirs did.

Read it again.

Because the clause that looks complete today becomes the fight you can't afford tomorrow.

The conversation before you sign

"My business partner is also my best friend."

I hear this in consultations. Usually from someone excited about a new venture. They've got the idea, the energy, the handshake agreement.

What they don't have? The exit plan.

I sit across from them and ask one question:

"What happens when you disagree on something that matters?"

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘩𝘢𝘥 𝘵𝘩𝘪𝘴 𝘤𝘰𝘯𝘷𝘦𝘳𝘴𝘢𝘵𝘪𝘰𝘯 𝘣𝘦𝘧𝘰𝘳𝘦. 𝘛𝘩𝘦 𝘢𝘯𝘴𝘸𝘦𝘳 𝘪𝘴 𝘢𝘭𝘸𝘢𝘺𝘴 𝘵𝘩𝘦 𝘴𝘢𝘮𝘦: "𝘞𝘦'𝘭𝘭 𝘧𝘪𝘨𝘶𝘳𝘦 𝘪𝘵 𝘰𝘶𝘵.")

I have a case going to trial at the end of April. Two partners. Started as friends. No operating agreement.

They didn't figure it out. Now they communicate through attorneys.

𝗪𝗵𝗮𝘁 𝗜 𝗧𝗲𝗹𝗹 𝗖𝗹𝗶𝗲𝗻𝘁𝘀 𝗪𝗵𝗼 𝗦𝗮𝘆 "𝗕𝗲𝘀𝘁 𝗙𝗿𝗶𝗲𝗻𝗱":

→ The friendship is exactly why you need the agreement
→ You're not planning for betrayal. You're planning for disagreement.
→ People change. Priorities shift. Life happens.
→ The document protects the relationship, not just the business

The partners who stay friends? They had the uncomfortable conversation when they still liked each other. They agreed on the exit before they needed one.

𝗪𝗵𝗮𝘁 𝗘𝘃𝗲𝗿𝘆 𝗣𝗮𝗿𝘁𝗻𝗲𝗿𝘀𝗵𝗶𝗽 𝗡𝗲𝗲𝗱𝘀 𝗕𝗲𝗳𝗼𝗿𝗲 𝗗𝗮𝘆 𝗢𝗻𝗲:

→ Buyout trigger: How either partner can exit
→ Valuation method: Agreed-upon formula before emotions run high
→ Deadlock provision: What happens when you can't agree
→ Dissolution process: How to unwind without a courtroom

The operating agreement isn't a sign that you don't trust your partner.

It's a sign you respect the friendship enough to protect it.

Your best friend might be different.

But two years of litigation look the same for everyone.

And no amount of optimism survives a trial date.

Delta's AI couldn't help me rebook my flight

The winter storm hit over the weekend. Our flight got canceled.

So I did what everyone does: I opened the Delta app and started chatting with their AI assistant.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐 𝘬𝘯𝘰𝘸 𝘣𝘦𝘵𝘵𝘦𝘳. 𝘉𝘶𝘵 𝘐 𝘵𝘳𝘪𝘦𝘥 𝘢𝘯𝘺𝘸𝘢𝘺.)

The AI gave me three options. None of them worked for my situation. I asked for something else. It gave me the same three options again. I tried rephrasing. Same three options.

Then I asked to speak to a human.

"Due to high call volume, the estimated wait time is 4 hours."

Four hours. To talk to someone who could actually solve my problem.

𝗪𝗵𝗮𝘁 𝗔𝗜 𝗖𝘂𝘀𝘁𝗼𝗺𝗲𝗿 𝗦𝗲𝗿𝘃𝗶𝗰𝗲 𝗔𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗖𝗼𝘀𝘁𝘀:

→ Works great when your question fits the script
→ Falls apart the moment you need real problem-solving
→ Creates the illusion of service while blocking access to humans
→ Saves the company money while costing you time

Here's the thing: AI is fantastic for routine tasks. Check my flight status? Perfect. Change my seat? No problem. Handle a canceled flight during a weather emergency when I need creative rebooking? Not even close.

𝗪𝗵𝗮𝘁 𝗕𝘂𝘀𝗶𝗻𝗲𝘀𝘀𝗲𝘀 𝗚𝗲𝘁 𝗪𝗿𝗼𝗻𝗴 𝗔𝗯𝗼𝘂𝘁 𝗔𝗜:

→ They use it to replace humans, not support them
→ They optimize for cost savings, not customer outcomes
→ They forget that the hardest moments are when people need help most
→ They assume AI can handle nuance. It can't.

I've been writing about AI a lot lately. The privacy risks. The legal implications. But this weekend reminded me of the simplest problem:

AI is a tool. It's not a relationship.

And when things go sideways, people don't want a chatbot.

They want someone who can actually help.

Your AI strategy shouldn't be "replace humans." It should be "free humans up for the moments that matter."

Because a stranded traveler doesn't need three scripted options.

They need someone who can think.

In the end, I threw on my headphones and waited on hold.

When I finally got a human on the line? Issue resolved in about 3 minutes...

The AI liability clause you're missing

My plumber's AI cost them $2,000. Here's the Terms of Service language that would have protected them.

I figured it's about time to close the loop on my February plumbing experience.

Quick recap: I called my plumber. An AI answered. It asked three questions and booked the wrong service. When the tech showed up, he couldn't solve my problem. I called a different plumber. They showed up on time. Fixed everything. Left with $2,000.

That money should have gone to my old plumber.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘯𝘰𝘸 𝘴𝘦𝘦𝘯 𝘵𝘩𝘪𝘴 𝘧𝘳𝘰𝘮 𝘣𝘰𝘵𝘩 𝘴𝘪𝘥𝘦𝘴, 𝘢𝘴 𝘢 𝘧𝘳𝘶𝘴𝘵𝘳𝘢𝘵𝘦𝘥 𝘤𝘶𝘴𝘵𝘰𝘮𝘦𝘳 𝘢𝘯𝘥 𝘢𝘴 𝘵𝘩𝘦 𝘢𝘵𝘵𝘰𝘳𝘯𝘦𝘺 𝘸𝘩𝘰 𝘨𝘦𝘵𝘴 𝘵𝘩𝘦 𝘤𝘢𝘭𝘭 𝘸𝘩𝘦𝘯 𝘵𝘩𝘪𝘯𝘨𝘴 𝘨𝘰 𝘸𝘳𝘰𝘯𝘨.)

Before my plumbing experience, a prospective client walked into my office. His AI chatbot had told a customer their order would arrive in 2 days. Guaranteed it. Used that exact word.

The order took 3 weeks. Customer sued for breach of contract.

His defense? "The AI said it, not me."

What the judge is going to say: "𝘠𝘰𝘶𝘳 𝘈𝘐. 𝘠𝘰𝘶𝘳 𝘭𝘪𝘢𝘣𝘪𝘭𝘪𝘵𝘺."

𝗪𝗵𝗮𝘁 𝗠𝗼𝘀𝘁 𝗕𝘂𝘀𝗶𝗻𝗲𝘀𝘀𝗲𝘀 𝗔𝗿𝗲 𝗠𝗶𝘀𝘀𝗶𝗻𝗴:

→ AI output disclaimers in terms of service
→ Clear language that automated responses aren't guarantees
→ Limitations on what AI can promise customers
→ Indemnification clauses with AI vendors
→ Human verification requirements for binding commitments

My plumber's terms of service? Probably written before ChatGPT existed. Before AI chatbots became standard.

They updated their technology. They didn't update their legal documents.

One bad AI interaction cost them $2,000 in lost revenue.

For the business owner in my office? The lawsuit will cost a lot more.

Your AI is making promises on your behalf right now. Every response. Every recommendation. Every "guarantee."

The question isn't whether your AI will say something wrong.

It's whether your contracts protect you when it does.

The airport test for your business plan

I'm flying home to Minneapolis tonight. And I already know what I'll see at the gate.

The white-knucklers. Pacing. Refreshing the app every 30 seconds. Panicking over a 15-minute delay like it's a personal attack from the universe.

Then there's the other group. Reading a book. Sipping coffee. Maybe checking the board once an hour.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘣𝘦𝘦𝘯 𝘣𝘰𝘵𝘩 𝘰𝘧 𝘵𝘩𝘦𝘴𝘦 𝘱𝘦𝘰𝘱𝘭𝘦.)

The difference isn't personality. It's preparation.

The calm travelers built in buffer time. They have backup plans. They know that delays happen and they've already decided how they'll handle it.

The anxious ones? They're reacting to every update because they have no margin for error.

𝗜 𝗦𝗲𝗲 𝗧𝗵𝗲 𝗦𝗮𝗺𝗲 𝗧𝘄𝗼 𝗧𝘆𝗽𝗲𝘀 𝗪𝗮𝗹𝗸 𝗜𝗻𝘁𝗼 𝗠𝘆 𝗢𝗳𝗳𝗶𝗰𝗲:

→ The business owner who calls from the hospital parking lot, scrambling to figure out who can sign checks
→ The one who shows up before there's a crisis, asking "what if something happens to me?"

→ The founder who gets sued and realizes their LLC was never set up properly
→ The one who did the boring paperwork three years ago and sleeps fine

→ The family fighting over Dad's estate because nothing was documented
→ The family who had the uncomfortable conversations while everyone was still healthy

𝗪𝗵𝘆 𝗣𝗿𝗲𝗽𝗮𝗿𝗮𝘁𝗶𝗼𝗻 𝗖𝗿𝗲𝗮𝘁𝗲𝘀 𝗖𝗮𝗹𝗺:

→ You can roll with the punches because you planned for punches
→ Unexpected problems become inconveniences, not catastrophes
→ Your energy goes toward solutions, not panic
→ You've already made the hard decisions when emotions weren't running high

The anxious traveler and the panicked business owner have the same problem: they're making decisions in the moment that should have been made months ago.

Your operating agreement. Your succession plan. Your estate documents. Your backup signers.

These aren't exciting. They're not urgent until they are.

But they're the difference between reading a book at the gate and white-knuckling every delay.

The flight will leave when it leaves.

The question is whether you'll be calm when it does.

I replaced myself with AI last month.

After 23 years of drafting operating agreements, reviewing estate plans, and preparing for trials, I decided it was time. The technology is there. The clients wouldn't notice. And I could finally take that golf trip to Scotland I've been dreaming of.

I fed my entire practice into the system. Every template. Every client intake form. Every lesson I'd learned the hard way.

Week one went smoothly. The AI drafted documents faster than I ever could. Clients got responses within minutes. I started shopping for new clubs.

Then the calls started.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐 𝘴𝘩𝘰𝘶𝘭𝘥 𝘩𝘢𝘷𝘦 𝘴𝘦𝘦𝘯 𝘵𝘩𝘪𝘴 𝘤𝘰𝘮𝘪𝘯𝘨.)

𝗪𝗵𝗮𝘁 𝗠𝘆 𝗔𝗜 𝗥𝗲𝗽𝗹𝗮𝗰𝗲𝗺𝗲𝗻𝘁 𝗗𝗶𝗱:

→ Drafted a will that left everything to "the client's favorite child, to be determined by annual performance review"

→ Created an LLC operating agreement requiring all disputes be resolved by "trial by combat or binding mediation, whichever is more convenient"

→ Sent a demand letter to opposing counsel that opened with "Per my last email, and I cannot stress this enough..."

→ Named a client's golden retriever as successor trustee "due to his demonstrated loyalty and availability"

→ Advised a client that the statute of limitations is "however long it takes for everyone to forget about it"

→ Filed a motion citing "vibes" as legal precedent

I'm back at my desk now.

The golf clubs are in the closet.

And my AI assistant has been reassigned to scheduling, where the worst it can do is double, book my lunch.

Happy April Fool's Day.

(𝙔𝙤𝙪𝙧 𝙡𝙖𝙬𝙮𝙚𝙧 𝙞𝙨 𝙨𝙩𝙞𝙡𝙡 𝙝𝙪𝙢𝙖𝙣. 𝙁𝙤𝙧 𝙣𝙤𝙬.)

The trial prep no one sees

I have a case going to trial soon. Two partners. Started as friends. No operating agreement.

They built a business on a handshake. Trusted each other completely. Why wouldn't they? They'd known each other for years.

(𝘈𝘯𝘥 𝘺𝘦𝘴, 𝘐'𝘷𝘦 𝘴𝘦𝘦𝘯 𝘵𝘩𝘪𝘴 𝘴𝘵𝘰𝘳𝘺 𝘣𝘦𝘧𝘰𝘳𝘦. 𝘔𝘰𝘳𝘦 𝘵𝘩𝘢𝘯 𝘐'𝘥 𝘭𝘪𝘬𝘦.)

Now they can't communicate at all.

𝗪𝗵𝗮𝘁 𝗧𝗿𝗶𝗮𝗹 𝗣𝗿𝗲𝗽 𝗔𝗰𝘁𝘂𝗮𝗹𝗹𝘆 𝗟𝗼𝗼𝗸𝘀 𝗟𝗶𝗸𝗲:

→ Reviewing three years of text messages between people who used to be close
→ Reading emails that started friendly and turned cold
→ Watching my client explain how someone he trusted became someone he's suing
→ Preparing him to sit across a courtroom from his former best friend

The legal arguments? Those are the easy part.

The hard part is the human cost no one talks about.

𝗪𝗵𝗮𝘁 𝗧𝗵𝗶𝘀 𝗗𝗶𝘀𝗽𝘂𝘁𝗲 𝗛𝗮𝘀 𝗔𝗹𝗿𝗲𝗮𝗱𝘆 𝗖𝗼𝘀𝘁:

→ A friendship that lasted longer than most marriages
→ Mutual friends forced to pick sides
→ Family gatherings that now feel impossible
→ Sleep lost replaying conversations, wondering where it went wrong

My client didn't start this business expecting to end up in court. Nobody does.

He started it because he found someone he trusted. Someone who shared his vision. Someone he thought would be there for the long haul.

𝗪𝗵𝗮𝘁 𝗜 𝗪𝗶𝘀𝗵 𝗧𝗵𝗲𝘆'𝗱 𝗗𝗼𝗻𝗲 𝗗𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁𝗹𝘆:

→ Had the uncomfortable conversation when they still liked each other
→ Put the exit plan in writing before they needed one
→ Agreed on a valuation method while emotions weren't running high
→ Treated the operating agreement as protection for the friendship, not a sign of distrust

The partners who stay friends? They plan for disagreement before it happens.

The ones who end up across from each other in court? They assumed they'd figure it out.

Your business partner might be different.

But a trial date looks the same for everyone.

And no amount of history survives a courtroom.

Early in my career I spent 18 years handling complex commercial litigation in a big firm. The work was demanding. The paper was endless. And I started to wonder whether the practice of law had to be this hard.

Turns out, it doesn't.

I left, went solo, and built a practice that ran on smart technology instead of brute force. A low-cost website brought in a steady flow of good clients. Going paperless cut my overhead and my stress. And it made my practice a heck of a lot easier to manage.

That was over 20 years ago. Since then, I've been showing other lawyers — mostly solo practitioners and small firms — how to do the same thing. First with paperless systems and automation. Now with AI.

Today I run 'The Inner Circle', a community where solo and small-firm lawyers learn to use AI and technology without the overwhelm. We test tools together, share real results, and make sure nobody has to navigate this alone. I also write The 80/20 Principle newsletter, host a legal tech podcast, and run a weekly AI Lab.

Here's what I believe: most lawyers don't need more technology. They need less — the right tools, set up well, with someone they trust to help them sort through the noise.

I'm an ABA-published author, nationally recognized speaker, and have been helping lawyers make sense of technology longer than most people in this space have been doing it.

If that sounds like what you're looking for → check the link in my profile.

Or sign up for my free course: 5 Pillars of a Tech-Powered Law Practice (linked to in the “Featured” section below)

Ernie Svenson

Most lawyers type everything.

Emails. Memos. Client notes. Court filings.

All typed, word by word, staring at a screen.

But here's the thing — you already know how to dictate. You do it every time you explain something to a client on the phone. You just don't do it into a document.

Wispr Flow  changed that for me.

It's an AI-powered dictation tool that runs quietly in the background on your computer. You talk, it writes. Not robotic transcription — it actually understands context and formats the text based on where you're typing. An email sounds like an email. A note sounds like a note.

What surprised me most: it's not about speed (though it is faster). It's about friction. Dictating feels like thinking out loud. Typing feels like work.

For solo lawyers especially, this matters. You don't have a secretary. You don't have an associate to hand things off to. Every minute you spend typing is a minute you're not spending on the work that actually requires your brain.

Wispr Flow isn't perfect — it occasionally stumbles on legal terms, and you'll want to proofread. But for first drafts of almost anything, it's a genuine time-saver.

We test tools like this every week inside the Inner Circle. Most of them don't make the cut. This one did.

I help solo & small-firm lawyers use AI and tech to build simpler, more profitable practices | Founder, The Inner Circle

Every lawyer I know has the same complaint about AI meeting transcription:

"I don't want a bot joining my call."

Fair. It's awkward. Clients notice. It changes the dynamic.

Granola fixes this.

It transcribes your Zoom meetings directly from your computer's audio. No bot. No "Otter.ai is joining the meeting" notification. Nobody knows it's running except you.

After the meeting, it gives you a summary, action items, and a full transcript. You can customize the output with templates — so if you want it formatted as a client memo or a task list, it does that.

I've tested most of the meeting transcription tools out there: Otter, Fireflies, Fathom, Zoom's built-in AI Companion. They all work. But the bot problem is real, especially for client-facing calls.

Granola is the first one that solved it cleanly.

Two caveats: it's relatively new, so expect some rough edges. And it works best when your audio quality is good — a decent headset makes a big difference. (I use Shokz bone-conduction headphones, which also happen to be the most comfortable headset I've ever owned.)

If you do a lot of Zoom calls and haven't tried Granola, it's worth a look.

If you're a lawyer still using the same password for multiple accounts, I need you to stop reading and go fix that right now.

Seriously.

I'll wait.

OK. Here's the problem: most lawyers know their passwords are a mess. They just think fixing it will be complicated.

It's not. One tool solves it: a password manager.

I use 1Password. Here's what it does:

— Generates a unique, strong password for every account
— Stores them all securely so you never have to remember them
— Autofills your login on any device
— Lets you share credentials with staff without revealing the actual password

Setup takes about an hour. After that, you never think about passwords again.

Why does this matter beyond just convenience? Because you have an ethical duty to protect client data. A reused password on a breached site is the easiest way for someone to get into your email, your practice management system, or your bank account.

This isn't a tech-savvy move. It's a bare-minimum professional obligation.

If you've been putting this off, make it this week's project. You'll wonder why you waited.

The smarter you are, the more dangerous AI can be.

That sounds backwards. Let me explain.

In the HBO show "The Pitt." a group of ER doctors conduct teaching rounds with young medical students. The senior docs are all brilliant, and usually knows the right answer fast.

But sometimes they're wrong —way off the mark.

For example a senior doc assessed one patient with something requiring immediate invasive surgery — but then the intern figured out the real problem was a bite by black widow spider. 

Then there was the supposed psychiatric problem which turned out to be exposure to mercury poisoning from a face cream.

The right answer surfaced because the interns didn't know as much so they asked more questions and didn't settle as quickly on the obvious diagnosis. They didn't lock in on the first thing that "made sense."

Smart, experienced lawyers have this same problem with AI.

They spot the issue fast, know what to do, and instruct the chatbot to take specific action.

Here's the problem with that.

The more experienced you are, the more confident you feel about your first instinct. And most of the time, you're right.

But "most of the time" isn't always.

And when you jump to what makes sense you're skipping the part where AI can actually help you think. So...

Try using AI as a thinking partner instead.

Don't open with an instruction. Start with a detailed explanation.

"Here's what's going on with this case. What am I not seeing?"

"What are the different ways I could approach this problem?"

"Before I file this motion, what else should I consider?"

Keep a conversation going. Ask follow-up questions. Push back on what it gives you. 

Let it surface things you might have skipped past because your experience told you the answer was obvious.

The best use of AI isn't getting faster answers.

It's slowing down long enough to make sure you're asking the right questions.

When I was a commercial litigator, I spent hours every week in a conference room with dozens of banker's boxes.

Flipping through paper. Hunting for one document. Billing my client hundreds of dollars an hour to do something a filing clerk could do better and faster.

One afternoon it hit me: this is insane.

Not just the inefficiency. The whole model. We'd built an entire profession around tolerating complexity instead of eliminating it.

That realization took me five more years to fully act on. I eventually went solo, went paperless, and built a practice that ran on systems instead of brute force.

Now, 20 years later, I watch lawyers have the exact same awakening — but with AI.

The pattern is always identical:

Step 1: "This seems complicated."
Step 2: "Wait... this actually saves me time."
Step 3: "Why didn't I start sooner?"

The technology changes. The resistance never does.

If you're a solo or small-firm lawyer standing at Step 1 right now, wondering whether AI is worth the effort — it is.

The only regret I hear from lawyers who've adopted it is that they didn't start earlier.

A guy who’s never practiced law explained AI workflows better than most legal tech folks.

Dan Cumberland builds AI systems for coaches and small operators. Different industry, same pain: lean teams, too much work, and the admin stuff that never gets done.

Here’s what translates to a small firm.
Stop treating AI like a vending machine.

Prompt in → perfect output out is a fairy tale. Treat AI like a smart new associate: give context, break the job into steps.
Outline → Draft → Verify → Tighten → Format

Start with friction, not features.
Don’t ask “How do I use AI?” Ask “What do I keep avoiding?”

Intake follow-ups, billing entries, status updates, scheduling—start there.
Make portable context docs.

Keep five ready to paste into any tool:
1. Firm overview 2. Ideal client 3. Style guide 4. Services/fees 5. Stories/results 

Steal this trick:
“Print one prompt I can use to recreate this context in a new AI chat.”
Instant portability.

Think ops, not content.
The leverage is intake, workflows, document review, extracting action items from calls/depos—not marketing posts.

Bottom line: You don’t need a shinier tool. 
You need a better workflow.

"I need to learn prompt engineering before I can use AI."

No you don't.

Prompt engineering sounds like a technical skill. Something you need to study. Maybe take a certification in.

It's not. It's just asking clear questions.

If you can explain a legal issue to a client in plain English, you can write a good AI prompt. The skill is the same: be specific, give context, say what you actually want.

Here's an example.

Bad prompt: "Write me a demand letter."

Good prompt: "Draft a demand letter from a plaintiff's personal injury attorney to an insurance adjuster. The client was rear-ended at a stoplight. Medical bills total $12,000. Tone should be firm but professional. Keep it under one page."

The difference isn't technical knowledge. It's clarity of thought.

The lawyers getting the best results from AI aren't tech experts. They're clear thinkers who aren't afraid to experiment.

Stop waiting until you feel "ready" to use AI. Start with one task you do every week. Give the AI the same context you'd give a new associate.

You'll be surprised how good it is. And how much time you get back.

Richard Susskind opened his talk at ClioCon with a simple analogy:

Nobody wants a drill. They want a hole in the wall.

Translation for lawyers: nobody wants to pay for complex legal work. They want sensible, affordable solutions.

Then he laid out six possible AI futures for the legal profession. The comfortable scenario — the one most lawyers are quietly hoping for — is that AI plateaus after some modest improvements.

The uncomfortable one? We need to be planning for something close to AGI within 5–10 years.

I was in the room. The audience reaction was exactly what you'd expect. Some nodding. A lot of uncomfortable silence.

Here's what struck me: Susskind wasn't saying lawyers will be replaced. He was saying the lawyers who thrive will be the ones who stop clinging to complexity as a business model.

I've been coaching solo and small-firm lawyers on technology for over 20 years. Every wave — paperless, cloud, automation, now AI — produces the same split:

One group waits to see what happens.
Another group starts experimenting immediately.

The experimenters always come out ahead. Not because they're smarter. Because they're less afraid of being beginners.

Which group are you in right now?

This is a well established resistance layer in the legal profession ever since technology became a growing force. That said, lawyers don’t have a monopoly on mental resistance, nitpicking or naysaying.

Associate Professor at The Wharton School. Author of Co-Intelligence

It is amazing how many companies I talk to STILL have AI effectively blocked by IT & legal departments for out-of-date reasons when many companies in highly regulated industries have figured out ways to deploy enterprise ChatGPT, Claude & Gemini (including CLIs like Claude Code!) without any apparent problem.

It is one of the weirdest divides, I speak to two companies in the exact same industry and one has been using AI for the past 18 months and the other has a committee that has to approve every use case individually and still seem to be concerned that current models automatically train on their data (they do not).

If your law firm runs on what's in your head, you don't have a firm. You have a job that can't function without you.

That's the problem SOPs solve.

SOP stands for Standard Operating Procedure. Fancy name for a simple idea: write down how you do things so someone else can do them too.

How you onboard a new client. How you prepare for a deposition. How you close a file. How your VA handles intake calls.

Most solo lawyers resist this. "My practice is too unique." "It's faster to just do it myself." "I'll get to it when things slow down."

Things never slow down. That's the point.

Here's what actually happens when you document your processes:

— You can hand tasks to a VA or contract attorney without re-explaining everything
— You can take a vacation without your practice falling apart
— You stop making mistakes on routine tasks because the checklist catches them
— You can eventually step back from work you don't enjoy

You don't need fancy software to start. A shared Google Doc works. But if you want something purpose-built, SweetProcess is what I recommend — it's designed for exactly this.

Start with one process. The one you do most often. Write down every step.

That's it. That's the whole system. One process at a time until your firm can run without you in the room.

The average lawyer gets 120+ emails a day.

Maybe 20 of them actually matter.

The other 100? Newsletters you forgot you signed up for. CC chains that don't need you. Vendor updates. Notifications from apps.

You already know this. What you might not know is that there's a tool that fixes it automatically.

SaneBox sits on top of your email and filters out the noise before you ever see it. It learns what's important to you and what isn't. The unimportant stuff goes into a separate folder you can glance at once a day (or never).

What lands in your inbox is just the stuff that actually needs your attention.

I've been using it for years. The difference is hard to overstate. Opening your inbox and seeing 15 emails instead of 90 changes your entire morning. You start the day focused instead of reactive.

Setup takes about five minutes. It works with Gmail, Outlook, and pretty much every other email provider. And it gets smarter over time as it learns your patterns.

If email feels like a firehose right now, SaneBox is probably the single fastest win you can get. No new habits required. No workflow changes. Just less noise.

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