Quick Answers

What should founders look for in a term sheet beyond valuation? Founders ought to prioritize more than just valuation: consider control provisions, anti-dilution protections (investor rights that adjust their ownership percentage if future funding rounds happen at a lower valuation — protecting the investor, but often at the founder’s expense), board composition, and fundraising flexibility. The most expensive capital often appears cheap at first glance.

What are the risks of signing a term sheet before getting a lawyer? Term sheets (non-binding documents that outline the key economic and governance terms of a proposed investment — think of them as the blueprint before the binding contracts are drafted) are not fully binding, but renegotiating agreed terms can be costly in both legal fees and investor goodwill. Getting counsel involved before you agree, not after, is what protects your position and leverage.

What is a SAFE, and how can it unexpectedly dilute founders? A SAFE (Simple Agreement for Future Equity) is an early-stage investment instrument that converts into equity at a later-priced round, and its dilutive impact varies widely. Founders who use template SAFEs without counsel often discover the full dilution effect when it’s too late or extremely costly to restructure.

The founder walked in beaming.

“I agreed to a term sheet. I barely gave up any of my company,” they said, smiling.

While my mouth said “That’s great,” my brain had other thoughts.

I hadn’t seen the term sheet before they signed.

Buckling my metaphorical seatbelt, I kept my smile and asked to take a look at the sheet.

The Fun Part: The valuation was high. It would definitely grab some headlines. The capital was real.

The Less-Enjoyable Part: The terms were heavily slanted toward the investor, with several of them being the type that I would have pushed back on, hard. Worse, they gave the investor enough control that the company would struggle to attract any subsequent investor at all.

This brings us to a recurring theme in early-stage fundraising: sometimes, the most expensive money a founder can take doesn’t look expensive at first.

What Founders Look at First (And What They Miss)

Most founders laser in on one number: valuation.

The headline figure. The one that gets screenshotted and shared. The one that they can brag about to friends.

Valuation matters, but founders who focus only on it miss terms that control who runs the company and holds real power.

These provisions don’t announce themselves as highlighted items on the terms sheet. There are four situations where I see these show up most often.

The Four Scenarios

1. Handshake deals with friends and family.

No documentation means no joint understanding of the deal. A friend who wires you money without paperwork may genuinely believe they have some degree of control, even if you know for a fact you explicitly told them otherwise. Arrangements without documentation can also damage your future fundraising: sophisticated investors will either walk away or demand documentation before they engage, requiring time, money, and runway (the amount of time a company has before it runs out of cash — typically expressed in months).

2. Desperate capital.

When the runway is short, founders accept terms they’d never take otherwise. The money makes them overlook control provisions (clauses that give investors the right to approve — or block — major company decisions, such as raising additional capital, selling the company, or adding board members), aggressive dilution, and constrained future optionality. Cash is necessary. But there’s a real difference between surviving and trading away the foundation of your company for ninety more days of runway.

I see this particularly in markets where capital is tighter (Cincinnati, Columbus, the wider Midwest). If you’re in one of these markets, do not fall victim to this trap.

3. The brand-name investor.

Conversations with the investor you regularly see and the media can feel like validation — and they can be. But investors with recognizable names know their brand carries value, and because business is business, they commonly price it into their terms. Taking money from a high-profile investor on tough terms can still be the right call, as it can serve as a signaling mechanism. The mistake is taking those terms without understanding exactly what you’re trading.

4. Template documents used without counsel.

Since Y Combinator made the SAFE template freely available, I’ve seen founders pull it and accept investment directly. This scenario keeps me up at night. Depending on how a SAFE is structured (particularly the valuation cap mechanics and whether it’s pre- or post-money), founders can give away significant equity without realizing it until much later.

The Checklist

Every situation is different. But before any founder takes capital or agrees to any deal, I walk them through the same core questions:

1. Does this deal contain control provisions? Do you understand what they are?

2. Would any of these terms make it harder to raise a subsequent round?

3. Is there a conversion feature? Do you understand exactly how it works?

4. What does this investor bring beyond capital, and do you want to be dealing with them in eighteen months?

5. If you had six months of runway left, would you still take this money on these terms?

The answers often reveal problems that get missed if the focus is only on valuation.

Back to the Founder

The founder in my office had answers to every item on that checklist. None of them was good for the company.

But the issue wasn’t the terms themselves.

It was the sequence.

They agreed to the term sheet first. Then came the checklist.

Term sheets may not be binding, but renegotiating terms already agreed to is costly in legal fees and goodwill. Once investors know you want the deal, your leverage diminishes.

Run the checklist before you agree. Not after.

The Takeaway

Valuation is the number founders celebrate. As the old saying goes, “the devil is in the deal’s details.”

Before signing or agreeing to a term sheet, slow down, run the checklist, and involve counsel early.

The most expensive money rarely looks expensive on the surface.

Your Next Move

Before your next investor conversation, write down the five checklist questions above. Answer them honestly. Before you’re in the room and have agreed to the terms.

​​If you found this useful, the Dispatch covers cap table mechanics, founder economics, and venture structure with a Midwest flavor every week — subscribe below.

Please note that all my answers are provided for entertainment value only. Nothing in any of my answers constitutes legal advice. Answers may contain facetious, ironic, or sarcastic comments. Always consult a qualified legal professional for advice on your rights and obligations. No communication we engage in or related to this page forms an attorney-client relationship. Please do not act or refrain from acting based on anything you see here or on any other social media or on any private messages we share. You become my client only once we have a signed agreement to that effect. I am licensed to practice law in Ohio.

Startups that skip early documentation risk losing investor trust, ownership harmony, and a steady foundation at the worst possible moment. Some of the most commonly missing documents are the cap table, governance structure, ownership transfer provisions, and new member procedures. Their absence can prevent capital from being raised in the first place.

“There is no way in hell I agreed to a 50/50 split.”

“That’s how I remember us doing it.”

“Well, I remember 60/40 because I’m bringing all of the technical knowledge.”

“Well, I’m not going to continue working for only 40%—I’m doing all of the hard work!”

Paper is cheap. The mistakes that come from skipping it are not.

The idea of moving fast and breaking things has its place in startups. But when it comes to your company’s legal foundation, a slower, more deliberate approach is better. Laying it out on paper will keep you from relying on memory and having conversations just like the one above.

Why Founders Don’t Document

In my practice, I see the above conversation all the time. Founders often rely on trust and handshake agreements to keep moving forward. It feels faster and easier in the moment.

The first reason is time. Founders skip documentation because it feels like a distraction from building.

The second reason is cost. Legal documentation requires a professional’s time, and founders naturally want to allocate every dollar toward growth, not paperwork.

Either way, the work gets deferred. Ultimately, the costs do not.

The Real Costs

Picture the due diligence call—an investor on one end, a founder scrambling on the other.

“Your company is great—can you tell us about your decision-making structure?”

“Oh, we’ll get that document to you.”

“Okay… well, can we take a look at your cap table?”

“Oh, we’ll get that to you, too.”

“Okay… we’re going to hold off until we can see those documents.”

A few days later:

“I think we’ll pass.”

In conversations like that, investors see a lack of structure, discipline, or savvy. No investor will overlook a certain amount of missing documentation, whether they are a large VC or a local angel. Some founders wait until after they’ve raised capital to document. That’s backward. The absence of that documentation can keep you from getting that very capital.

When it’s time to clean things up, the company usually needs to bring in counsel to create the right documents. Because everyone is working from memory, reaching agreement takes much more time and money than it would have cost to document correctly from the start.

The Things Most Often Left Undocumented

Believe it or not, these aren’t the most complex items. But, they’re still the ones I most commonly see missing:

• The company’s capitalization table—including all handshake deals and promises.

• The decision-making and tie-breaking process—the real mechanics of governance.

• Provisions for transfer of ownership—how and when someone can exit, and what happens to their shares.

• Procedures for admitting new members—who gets a seat at the table, and who decides that

What To Do

The goal is to have some order behind the startup chaos. Once your company reaches a certain point, it makes sense to work with counsel to turn those handshake agreements and memories into actual, concrete documents. That is what counsel is there for.

If you’re not there yet, start with a shared Google Doc. Use simple templates—a meeting notes outline or a lightweight cap table. Pick a format that feels easy to update so documenting doesn’t become a chore.

Then, aim to capture these with each entry consistently:

General Guidelines

• The time a conversation or event happened

• A brief synopsis of the conversation or event

• Any decision made at the end of the conversation

Specific Events to Capture

• Any promises made to anyone (employees, customers, suppliers)

• Any governmental notices

• Any formation or other legal action taken by the company

• Any hires, with a breakdown of their arrangement

When it is time to hire counsel, having this document ready will make the process much smoother. And do not worry - your list does not have to be perfect or exhaustive.

Paper is cheap. The credibility you lose when you can’t produce a basic document is not. Start the doc today.

If this piece was useful, forward it to a founder who needs it, or share it with someone building their first company.

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A friend said something to me recently that I keep thinking about.

“I have three customers. I think it’s time to raise money.”

I understood the excitement; landing real customers is a real milestone. But I asked a few clarifying questions. How many customers, exactly? What’s actually driving the decision to raise right now?

The answers were not concrete and instead seemed to cover up the real reasons.

Veterans of venture capital will tell you that fundraising is a tool to help your business meet its goals. It is not the goal itself. So why does it keep feeling like the main event?

Three patterns keep showing up when I dig into this with founders — and one of them rarely gets named.

Three patterns that push founders to raise too early

• The scoreboard effect

Headlines about round sizes make it easy to treat fundraising as a metric. When peers announce raises, it can feel like you’re falling behind — even when your business is on a completely different trajectory that doesn’t need outside capital yet.

• The momentum illusion

Raising a round feels like forward motion. Sometimes it is. But often, the real motion is solving a product, distribution, or demand problem — and capital doesn’t fix those. It accelerates them, in both directions.

• The competitive reflex

When someone in your market raises, the instinct is to match it. That instinct is understandable. It’s also not a fundraising strategy.

What makes these patterns dangerous isn’t that they’re irrational. It’s that they’re contagious. And the data makes clear where that contagion leads.

Let’s look at what actually happens when founders raise before they’re ready.

What the data actually shows

75% of venture-backed startups fail to return a single dollar to their investors — often because they scaled before solving for real customer demand. (Harvard Business School)

74% of high-growth startup failures in US tech resulted not from a lack of funding, but from spending raised capital on rapid scaling before the company had product-market fit. (World Metrics / Duet Partners)

If raising as early and largely as possible were the ideal strategy, the failure rates would not be this consistent. There is a pattern here, and it has a name.

That name is Blitzscaling — and most founders are misapplying it.

Why Blitzscaling isn’t what most founders think it is

Blitzscaling is the deliberate prioritization of speed over efficiency in markets where coming in second means losing everything. Reid Hoffman’s book of the same title described the logic bluntly: “Grow Fast or Die Slow.”

In true winner-take-all markets (where network effects allow one dominant player to capture nearly all industry value) the strategy is rational. Timing matters more than efficiency.

The problem isn’t the strategy itself. It’s that those markets are rare, almost exclusively in tech, and most founders aren’t in one. Walking into an investor meeting with a Blitzscaling pitch for a business that doesn’t operate in a winner-take-all dynamic won’t accelerate your raise. It will end it.

Which brings us to the conversation that actually started this post.

What peer pressure actually sounds like

A client came to me earlier this year. Here’s roughly how it went:

Client: “Jake, I want to do my Series Seed now.”

Jake: “That’s great. Did you just get a big order you need capital to fill?”

Client: “Well, no.”

Jake: “Do you need to hire to increase production speed?”

Client: “Not really.”

Jake: “We already talked about not raising as fast as possible just to raise. So what’s driving this?”

Client: “I saw headlines about [competitor]’s raise. Our product is better — so we should do it too.”

That’s not strategy. That’s a scoreboard.

So when does it actually make sense?

Three reasons investors actually get behind

1. You have clear customer demand you cannot meet without additional resources, and capital would help you scale into that demand.

2. You have found product-market fit and need to extend your product, or you need capital to build your first version in a capital-intensive category.

3. You are facing a specific bottleneck — a key hire, a production constraint, a market window — that capital can clearly and directly solve.

There are good reasons to raise capital. Peer pressure is not one of them.

Raising money isn’t the finish line. Building something people actually want is.

Once you’ve done that — once you have demand you can’t meet, a fit you’re ready to extend, or a specific constraint capital can solve — the conversation with counsel changes entirely.

Then you can walk into that meeting and say, with real conviction:

“I think it’s time to raise money.”

Most people see disability and assume fragility.
My life has taught me the opposite.

A Personal Note for Cerebral Palsy Awareness Month

March is National Cerebral Palsy Awareness Month.

So, I’m taking a break from my usual venture capital ramblings to talk about how CP has molded my life. I’ll share some thoughts, a few lessons learned, and hopefully some useful advice for anyone living with a disability or supporting someone who is.

What’s my goal? Of course, raising awareness and maybe inspiring someone would be great. But honestly, I just want to make it less awkward to talk about disabilities, share what I’ve learned, and hopefully do my part to shatter a few stereotypes along the way.

Breaking the Stereotypes

Let’s talk about a few stereotypes that just won’t seem to go away about physical disabilities. You’ve probably heard them before.

First up: the Fragility Myth. People see a physical disability and instantly think it means physical weakness.

Second, there’s the idea of the Passive Recipient. The assumption here is that people with disabilities have to sit around and wait for help, instead of having the agency to build a life that works for them.

And third, the Lowered Ceiling. This is the loud-but-unspoken expectation that if you have a disability, just getting by is the best you can hope for, rather than mastery.

The Strenuous Life

If you want to know my life philosophy, I actually carry a reminder of it on my arm:

Wear Out or Rust Out.

That phrase comes from Theodore Roosevelt. His approach to life taught me you don’t have to accept the stereotypes other people try to stick on you.

Most people remember Roosevelt as the Rough Rider or the face on Mount Rushmore.

However, he wasn’t born a mountain of a man. He started out as a frail, asthmatic kid who struggled just to breathe.

His father once told him that he had the mind but not the body, and that without the body, the mind could never reach its full potential. The solution was simple but demanding: he would have to make his body.

Roosevelt didn’t avoid physical activity (AKA, buy into the fragility myth), accept whatever life gave him (AKA be the passive recepient), or accept that he would never live up to the already legendary Roosevelt name because of how he was born (AKA giving into the lowered celing) He built his health, life, and legacy, with the help of his family and through hard work..

As a kid, Teddy’s family built a small gym in their New York home. He spent years climbing pegboards and hanging from bars, slowly turning himself into the living example of what he later called the strenuous life.

Bringing The Body to The Mind

Breaking the Fragility Myth

Too often, popular culture paints disabled people as fragile, like we’re all just one bump away from breaking. It’s as if we’re all versions of “Mr. Glass,” rolling or walking through the world.

Believe it or not, even some people whose job is to help those with disabilities buy into this idea.

Growing up and even now, many therapists and trainers just wanted me to “get by.” For a while, I assumed that was how things were supposed to be.

Then I read Theodore Rex and learned Roosevelt’s story. That’s when I realized that just like him, I had the chance to work on my body every single day.

So I started looking for therapists and trainers who would push me harder than their other clients. People who wouldn’t give me permission to make excuses.

Eventually, I realized I wasn’t fragile and that hard physical activity wouldn’t break me.

Instead of sitting back and rusting out, I was choosing to wear out.

Instead of sitting back and rusting out, I was choosing to wear out.

If you have a disability (or someone in your life does), I encourage you to find your own life mantra. The world isn’t always easy for people with disabilities, so you need something to guide you through the tough days.

For me, it’s “wear out, not rust out,” but here are a few others worth considering:

• Progress, not perfection.

• Adapt, don’t quit.

• Lead with what you CAN do.

Along with a mantra, a daily routine can also help.

Maybe that’s setting a goal to walk or wheel a certain distance, closing your Apple Watch rings, keeping a gratitude journal, or even just spending 10 minutes each morning thinking about what you want to accomplish.

These small habits add up and help shift your mindset over time, and reinforce that mantra. The important thing is to pick something that actually means something to you and slowly but surely gets you to push your limits.

But physical strength was only the first stereotype I had to break.

Agency

Breaking the Myth of the Passive Recipient

Moving beyond physical strength, let’s consider the myth of passivity and lack of agency.

For me, this stereotype wasn’t as much about what others thought. Regretfully, it was something I struggled with on the inside.

As may be shocking for those who know me, one of the hardest things I’ve had to learn as someone with a disability is having the courage to ask for what I need.

Maybe it was feeling like I should just be grateful for the help I already got, or maybe it was the fear of hearing “no.”

I struggled with this well into my twenties, until I came across some posts from other people with disabilities.

Reading those posts led me to a “duh” realization: everyone’s disability looks different, and nobody else can see your day-to-day challenges. Most people want to help, but it’s up to you to ask for what you need.

Everyone’s disability looks different, and nobody else can see your day-to-day challenges.

This realization made my life immeasurably easier, and while I am not one to regret the past, I do catch myself thinking about how much easier my life would have been had I developed this sense of agency sooner.

I would have chosen to live in an apartment that was actually handicapped-accessible, instead of thinking, “This is the best I can do.”

I would have asked for a different model wheelchair when the one I originally had did not fit my lifestyle.

I would have told my physical therapists they weren’t pushing me as hard as I wanted.

If you know someone with a disability, please do whatever you can to help them build a sense of agency. It doesn’t happen overnight, but even gradual improvement will get them there. Encourage them to speak up about what they need, set boundaries, and make their own choices in everyday situations. Help them set related goals, such as asking for a classroom accommodation or handling a routine task independently. Celebrate every bit of progress, no matter how small; it can have an outsized impact on their future.

You CAN Do That

Breaking the Stereotype of the Lowered Ceiling

Just like the lack of agency, the idea of a lowered ceiling for people with disabilities didn’t really become visible to me later in life.

However, this stereotype was purely external.

Growing up, my adoptive parents were always my biggest cheerleaders. They backed every crazy idea I had—cartoonist, comedian, author, football coach, venture lawyer, Shark Tank investor, you name it.

Sure, my disability made some parts of those careers harder. But my parents never said, “disabled people can’t do that.” Instead, it was always:

“That’s great! Let’s figure out how you can do it.”

As I grew up and moved into adulthood, I assumed that this was how everyone operated around people with disabilities. Encouraging, supporting, and helping them figure out their path.

In my first few entry-level jobs, nothing I saw made me think otherwise.

But once I started practicing as a venture lawyer, that view got shattered.

Initially, when I would tell people where I worked, and they would come back with “as a lawyer?” I was extremely confused. “Well, yeah, as a lawyer. Most people who work at law firms are, in fact, lawyers.”

It wasn’t until I talked with a friend about why this kept happening that it finally clicked:

There is a stereotype that disabled people can’t have jobs like mine.

That insight struck me like an overhand right that I never saw coming. Maybe people assume there’s a mental impairment, too, or maybe it’s just ignorance.

Either way, this is actually the easiest stereotype to disprove.

I highlight my disability and my career as a way to both break this stereotype and to show people like me that it is possible to do what you want to do in life, regardless of others’ expectations.

If you know someone facing these same issues, here’s what I’d suggest: First, follow my parents’ lead and ask, “How can we make this happen?” instead of “That’s not for you.” Second, help them find role models in similar situations. Third, talk openly about the lowered ceiling stereotype so they’re ready to push back against it.

Conclusion

It’s easy to let the world’s stories become our own: that physical challenges mean mental weakness, that people with disabilities are bystanders, or that just getting by is enough.

But none of these are facts. They’re just barriers, and every day, we get a chance to break them down.

A Note to Disabled Readers

To disabled readers: you’re not here to fit someone else’s idea of limitation. You’re here to create, to pursue, and to define success on your own terms.

A Note to Allies and Onlookers

To allies and onlookers: challenge the stories you’ve inherited. Look past fragility, passivity, and fake ceilings. Look for the resourcefulness and ambition that are always there, even if they go unnoticed.

Decide how you want to live each day. Take action, challenge limits, and encourage change in yourself and those around you.

Choose to wear out, not rust out.

Take control, defy limits, and lead by example starting today.

Closing Note

Thanks for reading.

If this essay resonated with you, consider sharing it with someone who might benefit from it—especially during Cerebral Palsy Awareness Month.

Sometimes the most powerful way to break a stereotype is simply to start a conversation.

If you know someone who needs this message, send it to them today.

Law students often ask me what it’s like to work in startup and venture capital law. I can picture what’s running through their minds: visions of working with the next big thing in tech, rocket-ship startups, and investors tossing around checks with more zeros than a phone number.

Of course, that world exists, and it is always fun to work on those deals. But it takes a lot of work to build a skillset that gets you there.

Every time someone asks me how to break into this field, I think back to law school and realize nobody actually tells you how to get from point A to point B. So, let’s fix that. I’ll walk you through what really matters in venture law, what the day-to-day looks like, and how you can actually get your foot in the door.

Venture law is less about courtroom drama and more about building the financial architecture behind high-growth companies. In this post, I’ll show law students a few steps to position themselves to break into the field, and preview what’s ahead: first, the core principles that drive venture practice; then, the realities of working with startups and funds; and finally, some practical advice to help you get started.

Let’s start with the basics: what matters most in this field, what it’s really like working with startups and funds, and, if you’re still with me by the end (God bless you), I’ll share a few tips that I wish someone had told me.

Part I: The Core of Venture Practice — It’s All About Structure

Venture Law Is Capital Architecture

At its core, venture law is all about understanding structures. If you’re hoping to argue about obscure case law, you’re in the wrong place.

If you’re working with startups, your first job is to figure out how the deal is actually put together. Who needs to sign off? (Spoiler: you’ll be tracking them down.) Who gets paid if things go well? How does the cap table change? If you get these basics, you’ll start to see why some points get fought over and others get waved through.

On the fund side, you’re the architect building the vehicles that pool and invest money. You’ll set up limited partnerships, general partners, management companies, side cars, SPVs, and more. Then you draft the agreements that hold all of it together and dictate how the whole machine runs.

Sounds like a lot? It is. But if you keep a few key questions in mind, you’ll be able to follow the deal and understand what’s really happening.

• Who controls downside?

• Who captures upside?

• Who controls consent?

• How are fees allocated across time?

• What happens if performance differs from expectations?

Almost every deal depends on these questions in some form or another. The faster you grasp the impact of these questions and their answers, the faster you will be able to contribute.

Fund Formation Structure — Long-Horizon Incentive Design

Working with startups and funds has a lot in common, but fund formation is its own animal. Don’t say I didn’t warn you.

Startup financings move fast because companies need cash, and time is short. With funds, time matters too, but in a different way. You’re helping clients set up a legal relationship that lasts 10 years or more. Every decision you make (compensation, governance, flexibility, control) sticks around for a decade. There’s no “just use the standard terms” here. You’ll spend a lot of time talking things through with clients and explaining why it matters. Some of the greatest hits are:

• Distribution waterfalls.

• Key person clauses.

• Removal rights.

• Regulatory compliance.

• The term of the fund.

• Management Fees.

Unlike startup work, which usually focuses on one company, fund formation is about building a web of entities and agreements that all have to work together for years. The learning curve is longer, and it takes more time to get your reps in.

The pace and focus are different, but those core questions still matter. Keep them front and center, keep learning, and you’ll be building big funds before you know it.

Part II: The Day-to-Day Reality — It’s Business First, Law Second, But Also The Other Way

Business Fluency Is Required

What’s the biggest thing that sets new lawyers in this space apart? Understanding business and what actually drives client decisions.

Most law schools barely touch business basics, so you’re left to figure it out on your own. And let’s be honest, nobody has time for that in law school or as a new associate. (Here’s a secret - you don’t get more free time later in your career!)

On the startup side, you need to understand key concepts like:

• incorporation, and the basic reasons for the choice of entity;

• What even is equity?

• What is vesting, and why does everyone seem to care about it?

• What does it mean to issue debt?

• What happens when a company raises money?

On the fund side, you need to understand even more esoteric concepts like:

• What is an investment thesis?

• The risk allocation model of venture.

• IRR versus multiple on invested capital,

• The psychology of limited partners (this may be the toughest of them all - worth its own article for sure!)

As you can see, startup and venture attorneys often get asked more than just legal questions. Although we are not technically business advisors, legal and business advice do bleed together. The most effective startup and venture lawyers I’ve seen have been able to blend the two - striking a balance between the business needs and the legal needs.

How do you learn these concepts? If your law school offers you the opportunity to earn credit for some business courses, take advantage of those as soon as possible.

If your school doesn’t offer business classes, you can always give up what little free time you have and teach yourself. Here are a couple of books that won’t make you an expert, but will help you get started:

• Personal MBA by Josh Kaufman

• Venture Deals by Brad Feld

Then, once you get your first legal job (likely not in the field of new ventures), try to get on as many deals as you can. Getting “more laps” will help you recognize what to focus on and allow you to begin to develop the most valuable skill for an attorney: judgment.

Communicating Across Experience Levels

You Operate Across Experience Levels

One of the things I still struggle with is speaking effectively across experience levels. Less experienced clients often want you to hold their hand, slowing down to explain every concept and decision (often times more than once!). They rely on you to translate legal jargon, walk through cap table math, and calm them at every step. And then, guess what, they often do the opposite of what you say anyway!

On the opposite end of the spectrum, more seasoned clients will skip past the basics and dive straight into complex business or structuring (there it is again!) issues that you never even thought of before, and they expect you to have an answer (or at least a credible-sounding plan for finding one) on the spot.

The only way to get good at handling both types? More reps. You’ll get them as you go. Again, get on every deal you can.

You might be thinking, “Okay, that’s great, Jake, but how do I actually get better at working with all these different clients right now?”

Here are a few things you can squeeze into your already shrinking free time (especially if you’re following all my advice):

Practice Clear Communication

One of the best ways to master a concept is to use the Feynman Technique—explain what you’ve just learned in plain English, as if you’re teaching it to a young person with no background in law or business (you have to watch out for that 9-year-old with a JD/MBA). As you do this, you’ll quickly discover the gaps in your own understanding and be forced to break down jargon and simplify information until it’s truly clear. This method not only helps less experienced clients but will also reinforce your knowledge.

Develop Active Listening

Clients do not say exactly what they need. Ever. Part of your job is to understand what they really need (more on this below). Focus on discerning patterns, hearing unsaid hesitations, and intuiting underlying concerns. Practice asking thoughtful follow-up questions, then saying something like “what I am hearing is this” to validate your understanding. These are habits you can develop now when talking with family, hanging out with friends (yes, I know, with what time), or even in classroom discussions (just don’t be a gunner!), and they’ll serve you well when the stakes are a bit higher.

Clients Rarely Know Their Legal Problem

One of the first things you’ll learn in this world: clients almost never come to you with a precise legal question.

If only startup and venture law were as tidy as your casebooks.

Instead, they share their story. The story is long. The story is out of chronological order. The story almost always seems to be missing the most important details that you need.

Your job is to listen carefully and, using the active listening skills discussed above (which I’m sure you’ve already practiced), sift through the reading of War and Peace to identify the real legal issue.

You can do this by asking clarifying questions, gently leading the conversation to fill in gaps (I, admittedly, still have to work on this one), and testing your interpretation by summarizing what you’re hearing.

Think of yourself as a sort of detective, thinking “hmm, what’s really going on here?” Being able to find this out sooner rather than later is another way you become an effective counselor rather than someone who just fills in the blanks.

Finding out the problem after two phone calls versus after you’re weeks into drafting documents is the difference between a very happy, long-term client and one you will probably not hear from again after you finish the transaction.

Part III: How to Break In — Build the Foundation First

Why You Should Start in M&A

Every young attorney I talk to wants to jump straight into venture as their first job.

Don’t do it.

Start in M&A instead.

Mergers and acquisitions teach you transactional fundamentals: consent requirements, representations and warranties, indemnification concepts, diligence processes, and closing logistics.

Understanding these concepts is table-stakes for understanding venture financings and fund formation. You are expected to spend your time learning the venture concepts as you work, not the business law fundamentals.

A year in M&A gives you the foundation to hit the ground running—instead of drowning and wondering if you picked the wrong career.

If you enter venture without that foundation, the pace can mask holes in knowledge. You may learn terminology without knowing what it means. You might learn what goes where without learning why.

Build your foundation first.

You might move slower at first, but you’ll end up with the skills that actually make you stand out.

Closing Thoughts: A Steep Curve, A Worthwhile Ride

Venture law is a wild ride. The learning curve is steep, but the payoff is worth it. You get to work at the intersection of law, business, and everything in between.

If you’re a law student or new associate thinking about this field, focus on building your foundation—clear communication, active listening, and judgment. These skills will pay off for years. Don’t get discouraged if it takes time to break in.

I’m always happy to give guidance or divulge more about the realities of venture practice, so don’t hesitate to reach out if you have questions or want advice. You can email me at jd@denhamdispatch.com or get in touch with me here on Substack.

I. Let’s Lower the Temperature

Let’s be real: nobody rolls out of bed thinking, “Today’s the day I get to hire a lawyer!”

You’re probably more worried about your runway, your next product launch, or whether AI is the only thing VCs care about this week.

Legal? It just feels like expensive, time-sucking overhead.

So let’s make this simple:

You bring in a venture lawyer right before you hit the point of no return: when things get real, and you can’t afford to mess it up.

Here’s how you know you’re there.

II. When It’s Too Early (Yes, That’s a Thing)

I have well-meaning founders come to me all the time, trying to do the right thing by hiring counsel at the very beginning, before they even have a company.

I usually tell them to keep me in the loop, but honestly, it’s probably too early for me to add real value.

Some signs that it may be too early to bring in a venture lawyer are:

• You’re still testing the idea.

• You have no sales.

• You’re still a solo act.

• You haven’t even thought about investors or partners.

At this stage:

• Set up your company the right way (online tools or solid templates work just fine at this stage).

• Keep ownership simple, clear, and written down somewhere you won’t lose it.

• Build.

If you’re a solo founder obsessing over your cap table before you even have customers, you’re probably focusing on the wrong thing. But if equity comes up, jot down what you agree on in a shared document — nothing fancy, just something you can find later when it’s time to get a lawyer involved. Keep it informal, but don’t trust your memory.

(For newer readers: a cap table (or capitalization table) shows who owns how much of the company.)

That table does matter.

But probably not right now.

III. First Real Trigger: When Equity Stops Being Theoretical

You need a venture lawyer the moment you make promises that are hard (read: expensive) to unwind.

That includes:

• Bringing on a co-founder.

• Granting equity.

• Issuing SAFEs.

• Agreeing to board seats.

(For newer readers: A SAFE (Simple Agreement for Future Equity) is a common early-stage investment instrument. Investors give you money now in exchange for equity later, usually when you raise.)

Bringing on a co-founder isn’t just about splitting work. You need to think about setting legal terms and economic terms, and consider how to handle disagreements after the initial buzz fades.

Granting equity, issuing a SAFE, or agreeing to board seats all create permanent legal commitments for your company.

Even small mistakes can be expensive or impossible to unwind later. Getting counsel at this stage will help you protect your interests, memorialize control, and prevent surprises.

If you’re at any of these junctures, you shouldn’t DIY.

IV. The Asymmetry Rule: Experience Is Leverage

If you’ve somehow made it to the point where you’re across from a potential investor who has done 100 venture deals, while this is your first time at bat, it is time to hire counsel.

They might seem friendly, but they know this game inside and out. The negotiation isn’t on a level playing field.

Seasoned investors experience and negotiate things like:

• Option pool expansions (setting aside shares for future employees — often increasing founder dilution if done pre-money).

• Protective provisions (special investor rights that require their approval for major decisions).

• Board composition (who actually controls governance).

All of these can shift power and control in your company in ways you won’t see coming.

If you don’t understand how they do those things, please don’t negotiate alone.

V. The Capital Threshold: Even “Small” Money Is Real Money

When you start bringing on capital, you should bring on counsel. And I don’t mean only when the seasoned investor from above comes knocking.

I’m talking about even when Uncle Bob wants to give you ten grand.

It’s common to take early money from friends and family, but doing so comes with risks.

If things go well, everyone is happy.

But if things get rocky (and let’s be honest, they usually do), unclear terms or handshake deals can turn into arguments, family drama, and legal difficulties.

Bringing in a lawyer early helps you put everything in writing, set expectations, and avoid misunderstandings that can wreck both your company and Thanksgiving dinner.

If you’re chatting with a potential investor and any of these words come up, take a break and get a lawyer:

• Liquidation preferences.

• Anti-dilution protections.

• Board control.

• Information rights.

• Future fundraising flexibility.

Trust isn’t a substitute for clear documentation and a solid, professional foundation.

A little legal understanding now is way cheaper than cleaning up a mess later.

VI. The Underdog Reality: Geography Changes the Risk

If you’re building outside traditional venture hubs (whether that’s Cincinnati or somewhere else), you must understand these terms and partner with counsel before it is too late.

In underdog markets, capital is tight. That means:

• You don’t get endless recapitalizations.

• VCs from other markets may try to get terms heavily in their favor.

• You’re fighting the “small market” stereotype every step of the way.

Bring in counsel at the right moment, then keep grinding.

VII. The Clean Framework: Know the Trigger. Act Deliberately.

When equity becomes real, lawyer up.

When capital comes knocking, lawyer up.

When your investment knowledge is outmatched, lawyer up.

Before those moments: grind and build.

After those moments, get strategic and intentional about your next moves — with the right experts in your corner.

Picking the right lawyer for your startup or fund? It’s a lot like choosing the person you want in the cockpit with you for a cross-country flight.

This isn’t a quick puddle-jumper.

A real journey, where tiny miscalculations compound and weather shifts without warning. Miss a single decimal point in your equity split now, and that 1 percent mistake could mean giving up way more of your company down the road. Suddenly, what looked like a rounding error at takeoff feels massive when you land.

You don’t want a co-pilot who can’t help you when turbulence hits.

You want someone who’s already in the cockpit with you, watching the same dials.
Eying the instruments.
Reading the sky.

And when the situation calls for a quick adjustment, they stay calm.

That’s exactly how working with your startup or venture lawyer should feel.

Familiar.
Technically precise.
Steady.

Because venture capital, corporate governance, and founder economics may utilize similar documents, the mechanics underlying them differ. And those differences become expensive when misunderstood.

What You’ll Be Able To Do After Reading

By the end of this article, you’ll know exactly how to evaluate startup or venture counsel with confidence.

You’ll walk away with:

• The key questions to ask

• The types of answers that reveal real expertise

• The clarity to separate true partners from polished talkers

In short, you’ll be ready to make a decision you can trust—not just hire an old friend.

The Quiet Problem Most Founders Face

Here’s the real challenge:

How are you supposed to hire someone to help you with dilution math, option pools, liquidation preferences, and board politics when you’re still figuring out what those even mean?

The truth is, almost every founder starts off feeling confused by this alphabet soup. If you’re scratching your head, you’re not alone.

If you’re early in your founder journey, all those terms can feel overwhelming.

Dilution simply means your ownership percentage shrinking as new capital comes in.

Option pools? That’s just equity set aside for your team—but how you set them up decides who actually takes the dilution hit.

Liquidation mechanics? That’s just a fancy way of saying who gets paid first if you sell the company.

These aren’t simply buzzwords to memorize.

They actually shape who owns what and who calls the shots.

And somehow, you’re supposed to judge who’s an expert in all this while you’re still learning the ropes.

That’s uncomfortable.

That’s why you need a real, experienced partner—not just a resume full of credentials.

The Founder’s Dashboard

Here’s the make-or-break truth:

The counsel relationship likely isn’t for a single transaction.
You’re picking someone who’s going to be in the cockpit with you for the long haul.

Pick wrong, and you won’t just feel it in annoying emails or slow responses.

You could feel it where it really hurts—your ownership.

Sure, a smooth ride is great.

But being protected in turbulence is even better.

The Red Flag Founders Miss

Although the model questions and answers below will help you, there is one very common red flag I see founders miss all the time.

It’s when a lawyer gives you a smooth, confident “yes” to every question—without specifics or substance.

Move Past Polished “Yes”

I know how it feels when looking for counsel. Those early lawyer conversations? They all start to sound the same.

“Have you done a Series Seed?”
Yes.

“Have you formed a venture fund?”
Yes.

You get clean answers—but no way of vetting their experience.

Don’t just collect yeses—test their judgment.

Ask for real specifics.

What was difficult?
Where did things almost break?
How did they handle a founder heading in an unexpected direction?

Real experience shows up in the details.

How To Vet Your Shortlist

Below, you’ll find model questions to ask potential counsel, along with the types of answers that reveal real expertise.

After reviewing them:

1. Make a shortlist of 2–4 lawyers or firms who could be a fit. Tap into founder networks, accelerators, industry events, or ask fellow founders and investors for referrals. A good referral will save you from a lot of the legwork (or wheelwork for some of us).

2. Schedule quick intro calls with each, using these questions as your guide.

3. Take notes on both their experiences and how clearly they communicate.

4. Compare, reflect, and pick your co-pilot.

The Questions That Reveal Real Experience

1. “What kinds of startups or funds do you work with most often?”

If someone says, “A little bit of everything,” it might sound versatile.

But it’s not what you want.

You want someone who knows your stage inside and out.

“I primarily work with Series Seed and Series A founders.”

That tells you they know where founders at your stage usually trip up.

Because the risks at pre-seed are totally different from the risks in a Series A, and both are a world away from running a fund.

Generalists can fill in the blanks.

Specialists and true co-pilots see around corners.

2. “What does your typical client look like at my stage?”

A good lawyer won’t just jump in with an answer.

They’ll ask you questions about your stage first.

Pre-seed?
Raising your first priced round?
Managing outside investors’ capital?

Your stage changes your risk profile.

And your risks decide what deserves attention.

3. “What usually goes wrong at this stage?”

This is where theory separates from cockpit time.

Listen carefully.

“At this stage, founders underestimate how option pool sizing affects dilution.”

“Here’s how a SAFE could change things.”

A SAFE is an early investment instrument that converts into equity later. If you stack too many SAFEs, your ownership can shrink quickly in your first priced round.

Those kinds of answers show they’ve seen the movie before.

You don’t need someone who only knows how things work when everything’s perfect.

You want someone who can spot the storm before it hits.

The Technical Co-Pilot

A good co-pilot actually wants you to know what all the instruments mean.

Pro rata rights — your ability to invest later to maintain ownership.
Capital calls — when fund managers request committed capital.
Liquidation mechanics — how proceeds are distributed when money comes back.

They don’t hide behind legal jargon.

They translate it into plain English.

Because founders who actually understand this stuff negotiate completely differently.

If your lawyer can’t explain these mechanics in plain English, you don’t want them next to you when things get tough.

In Conclusion: Pick For Turbulence

At the end of the day, your co-pilot sets the tone for your whole journey.

Pick someone who’s disciplined.
Who’s been through it before.
And who doesn’t flinch when things get turbulent.

Because building something that matters almost never happens when the skies are clear.

Your Next Move

Ask yourself:

From the list you made earlier, which single question will test potential counsel the most on your next call?

Then take it a step further.

Pick one lawyer from your shortlist and schedule an introductory call this week.

Taking that first meeting is the surest way to move from learning into action—and start building the next big thing.

AI is making a lot of noise in the workplace, but I have a question that has been eating me up inside: are we actually thinking about how to grow talent while “the robots are coming for our jobs”?

If you’re early in your career, you’re probably wondering (loudly and with good reason): Is AI about to take my entry-level job?

Meanwhile, business leaders are doing what they do best by asking if they can save a pile of money by swapping people for AI. (Spoiler: probably not if you’re thinking about replacing your lawyer.)

AI can do some incredible things, no doubt.

But the real issue isn’t whether AI can check a box or finish a task.

The real challenge for everyone (job seekers, new hires, startups, and big companies) is this:

Are we, together, actually building the next generation of talent, or are we just letting AI eat all the entry-level work?

Here’s what I want to tackle in this Denham Dispatch:

First, for anyone just starting out: how do you actually add value and build a career when it feels like AI is doing everything you were hired to do? The answer: focus on the soft skills and the little things. This is the stuff AI just can’t do. That’s how you become someone with real skills and capabilities, rather than just a task robot.

Second, for established businesses: a word of caution before you swap out your entry-level folks for AI. Sure, you might save a few bucks in the short term, but you’re risking your talent pipeline, AKA your real long-term edge.

For startups, I want to highlight why the AI temptation is even more dangerous. When you’re building a company from scratch, every person needs to grow into multiple roles. Skip that growth, and you’ll find yourself with capabilities gaps at the worst possible time.

For New Employees

You keep hearing that AI is coming for all the classic entry-level tasks: putting together presentations, reviewing contracts, and scheduling meetings. And yes, that’s happening. But it doesn’t mean you’re doomed if you’re new on the job.

If you’re doing these kinds of tasks as a new hire, here’s the secret: at the best companies, your job isn’t just about checking “task complete” box. Each task is actually a designed chance to learn something deeper that will help you level up in your career.

Putting together a finalized presentation is a way for you to understand the big picture of a transaction, deal, or pitch, so you can see why things are structured the way they are.

Reviewing a contract is a way for you to learn what the key terms are in your industry, so you can learn what certain things are heavily negotiated, and why. Then, one day, you will be able to negotiate them.

Scheduling meetings is a way to get your name in front of decision-makers for the companies your employer works with. It’s not about who you know; it’s about who knows you.

See the pattern?

Every one of these tasks has a hidden lesson.

If you concentrate on mastering those skills and grabbing those opportunities, the robot overlords will struggle mightily to take your job.

For Established Businesses

If you’re running a business, you’re probably feeling the squeeze to keep costs down. Either from your board, your management team, or just the reality of the numbers.

That’s where the AI pitch starts to sound pretty good. For less than the cost of an entry-level salary, you can keep expenses down and maybe even boost productivity.

But here’s the thing: we’re still in the early innings of the AI game. Maybe these productivity gains will be world-changing, maybe not. But there’s another angle to think about before you start swapping out your entry-level team for AI.

You might win in the short term, but you’re giving up long-term gains and your competitive edge.

In plain English: you’re wrecking your talent pipeline, and that’s a mistake you’ll feel for years.

Executives in every field always speak about how they prefer to grow talent from within their organizations rather than paying hefty sums to bring in developed professionals from the outside.

This is especially true in my field of law and (in professional services generally). One of the secrets of the legal profession is that law school doesn’t actually teach students how to be a lawyer. Because of this, firms often have to invest several years of teaching into an associate to help them develop skills and a specialization to help their career and the firm take off.

Think of those entry-level tasks that seem ripe for AI replacement. They have value beyond simply “completing the task.” When a junior associate reviews a contract, they’re not just running down a checklist and filling in brackets. They’re also learning to spot issues, understand client priorities, and develop judgment. When they compile research, they’re also building a mental model of how deals are structured. Replace those “also” learnings with AI, and five years later, you’ll have a senior associate who can prompt an AI but can’t make decisions on their own.

The same principle applies across industries. Entry-level employees aren’t just doing tasks—they’re developing into your future leaders. Cut that development short, and you’ll find yourself with a hollowed-out organization: senior people with no one ready to replace them, and junior people who never learned the fundamentals.

For Startups In Particular

For startups, the AI pitch is even more tempting. Money is tight, timelines are crazy, and you’ll likely have to pivot just to survive. Cheap, fast, and always-on AI sounds like the answer to all your problems.

But here’s the catch: all the downsides of replacing people with AI are even bigger for startups.

If you’re a startup, you can’t afford to have people who only do one thing. Your lead coder is also helping with marketing. Your best marketer is jumping in on customer support. Your CEO is doing everything from hiring to bookkeeping to writing a little code.

Opting to use AI rather than having employees get their feet wet with these tasks will ensure the skills never develop. And, unlike in a more established business, startups likely do not have the resources to hire someone with these skills if AI can’t do something.

Talent development isn’t a luxury. It’s your competitive edge.

Whether you’re just starting a business or deep into running one, the real question isn’t “can AI do this task?” It’s “What skills are we actually building in our people?”

So, What To Do

Entry Level

For new entry-level employees, focus on the “why” of the tasks you are doing to develop that all-important context.

Ask questions and lots of them. When you get a task, don’t just do it. Figure out why it matters. Why is this presentation set up like this? Why does this contract term always get so much attention? Why does this client always want morning meetings? The answers are where you build the skills AI can’t touch.

Get in front of decision makers whenever you can. AI can write the email, but it can’t build a business relationship. Volunteer for client meetings, even if you’re just there to take notes. When you schedule a meeting, add a smart internal note showing that you get the bigger picture. People remember who shows up and adds value.

Take on the unclear and soft-skill problems. AI is great at tasks with explicit instructions, but it falls apart when things get fuzzy. If there’s no template, that’s your chance to jump in. If people are butting heads, help resolve the issue. That’s where you prove your value.

Make a point to learn how things really work. Watch how decisions get made, which projects flopped and why, and which clients have their own quirks. Write down what you learn. That’s the kind of knowledge that makes you irreplaceable.

Most important of all: your job isn’t just to check off tasks. It’s to build real skills. Every assignment is a chance to get better at something that will help you for years. AI can do the work, but only you can build your career.

For Established Businesses

Protect your talent pipeline. Sure, AI can handle a lot of entry-level work, but those tasks aren’t only about getting things done. They’re about building your future team. Before you swap out junior roles for AI, ask yourself: who’s going to be ready to lead in five years? Who’s going to know how things really work?

Be intentional about developing your people. If you’re using AI for the routine stuff, make sure your junior employees still get substantive learning experiences. Rotate them through different teams. Let them sit in on client calls. Give them projects outside of their typical team. The goal: make sure they’re still building the skills they’d get from those “AI-able” tasks.

Double down on mentorship. AI can finish a task, but it can’t explain why your company does things a certain way or help a new hire figure out the politics of a deal. Senior folks need to spend more time, not less, helping junior employees understand the why behind the work.

Track whether your people are actually growing, not simply getting tasks done. Are your junior employees learning to think strategically? Are they building relationships? Are they developing judgment? If AI is getting the work done but your people aren’t getting better, you’re winning the short game and losing the long one.

For Startups

From day one, hire people who can learn quickly and wear many hats. In a startup, you can’t afford one-trick ponies. Bring on people who want to grow, and give them the chance to actually do it.

Treat every hire like they could be your next leader. That first customer support person might end up running product. Your first ops hire could be your future COO. Make sure they get the experience they need to grow into those roles. Let them wrestle with the tough stuff instead of just handing it all to AI.

Build a culture where everyone is expected to keep learning. Celebrate when someone picks up a new skill. Give people room to learn by doing, even if AI could do it faster. Your startup’s long-term success depends on having a team that can adapt and grow.

Closing

The AI revolution is real, but it’s not the story we think it is. The question isn’t whether AI can do entry-level work. The question is whether we’re building the capabilities and skills employees need for the future.

For individuals, this means treating every task as a chance for learning. You do this by focusing relentlessly on developing the judgment, relationships, and contextual knowledge that AI cannot duplicate. Your career isn’t built on tasks completed, and it’s built on capabilities developed.

For businesses, remember: entry-level employees aren’t just a line item. They’re your future. Saving money with AI now can leave you with big gaps later that cost way more to fix. The winners won’t be the companies that replaced junior employees the fastest. The winners will be those who figured out how to actually develop talent in the age of AI.

We’re not facing a choice between humans and AI.
We’re facing a choice between building capabilities and optimizing for task completion.

Choose wisely.

When a legendary VC posted that he used AI to close a financing without lawyers, I could hear founders and fund managers everywhere in my head asking the same question:

Do I still need my lawyer, or am I just burning money?

Recently, Venture Capital stalwart and all-around cool guy Brad Feld published an article detailing how he used a Google LLM and precedent documents to complete an early-stage financing, thus bypassing legal counsel and avoiding his firm’s proposed $50,000 fee.

While I could spend this whole article taking a huge pro-AI or anti-AI stance, you’re probably more interested in what Brad actually did here: choosing not to use counsel.

Whether you’re a founder raising capital or a fund manager deploying it, I can imagine you asking:

“Do I not need my lawyer anymore? $50,000 and dealing with you, or $0 and bossing ChatGPT around? Sign me up!”

I don’t think Brad was dismissing lawyers or declaring them obsolete. His post reads more like an observation from someone deeply experienced, who remembers the era before standardized documents (I am very glad I was not practicing back then!).

So, can you ditch your counsel like this venture capital veteran did?

The answer is, “despite what people think, probably not.”

A Critical Distinction

Before we go any further, it’s important to say this plainly:

This approach works for people who already know exactly what “good” looks like—because they’ve seen hundreds of deals from the inside.

For everyone else, the risk isn’t that AI can’t put words together to make a document.

AI is pretty good at following commands.

The risk is that you won’t know when it drafts something dangerous.

What Makes This Situation Different

Let’s focus on what makes Brad’s position unique compared to founders and fund managers asking whether they can replace their counsel with ChatGPT.

He has more knowledge than almost anyone in venture capital (but maybe not you after regularly reading this newsletter!). He’s done the deals and likely knows more than many attorneys and dealmakers.

Second, he used a Google LLM after feeding it substantial precedent documentation. Brad’s years of experience allowed him to understand precisely what he wanted from the deal and to curate the right examples to feed the LLM.

The Questions You Should Be Asking Yourself

These two factors present a few questions for those thinking they can do as Brad did:

First, do you have Brad’s depth of expertise to judge whether the AI’s output follows market standards and protects your interests?

Second, do you have high-quality precedent documents to train the AI, along with the judgment to select the right ones?

If you’re raising your first priced round or deploying your first fund and don’t know how liquidation preferences, pro rata rights, or protective provisions can blow up in your face (or in your portfolio companies’ faces), you don’t yet have the judgment layer AI can’t supply.

The Price Question Everyone Asks

You may be thinking: If most people can’t rely solely on a $20-a-month ChatGPT subscription, why do I still need expensive legal counsel?

Whether you’re managing a fund or building a startup, there’s a massive price gap! What exactly am I paying for?

The problem with comparing AI to legal counsel isn’t the price gap—it’s the risk gap.

AI mistakes are cheap up front and devastating later (I’ve spent a lot of time cleaning them up).

Legal mistakes tend to rear their heads when you have the least amount of time to deal with them.

What You’re Actually Paying For

Contrary to popular belief, you’re not paying lawyers just to “fill in the blanks.”

You’re paying for your attorney’s insights and judgment. Those are the real values beneath the words they draft.

You’re paying them to:

• Apply their judgment to ensure you don’t optimize for “standard” terms that don’t meet your specific needs.

• Help you determine what’s actually urgent versus what’s posturing or a shakedown.

• Connect you with their network of specialists who can help in other areas of your business.

Where AI Fits — and Where It Doesn’t

AI is no doubt a revolutionary tool, and Brad Feld’s experience is a great use case.

But tools are only as effective as the person using them.

Brad didn’t succeed because of the AI; he succeeded because of the decades of expertise he brought to it.

The real question isn’t whether AI can generate legal documents. It can (pretty badly).

The question is whether you have the judgment to know if those documents advance your interests, protect your future, reflect actual market standards, and don’t just “sound good.”

Final Thought

Attorneys aren’t there to fill in blanks or perform tasks a machine could handle.

We’re there to ask the questions you don’t know to ask, spot the risks you can’t see, and draw on pattern recognition across hundreds of deals.

We’re there to tell you when something that sounds standard is actually a red flag or when you’re being taken for a ride.

In the end, what you need isn’t just someone who knows the magic words.

You need someone who knows which words matter for you.

One of the losingest programs in major college football won the national title. To put the turnaround in perspective, Indiana Football still has the most losses of any program in major college football history and had zero double-digit-win seasons in 135 years of existence!

Unlike most title contenders who take time to build up, the Hoosiers went from nothing to something in just two seasons, after the hiring of a curmudgeon coach from lower-level James Madison University, Curt Cignetti. Not only did Cignetti bring his coaching staff with him (most of whom have been together for decades), but he also brought a ton of players from James Madison.

Experts mocked him and his players with insults ranging from “Why Indiana?” to “Those kids will not be able to compete at the higher levels.”

Now, two short years later, that same team sits atop the college football universe. So much for not being able to compete.

Watching Indiana steamroll Alabama and Oregon, and then dispatching the mighty Hurricanes, I found myself wondering why I was rooting so hard for the Hoosiers—especially since they beat my beloved Buckeyes in the Big Ten championship game.

Then, it hit me.

Why I Was Rooting for Indiana

Not only did this story unfold in the world I knew before Venture Capital—college football—but the Hoosiers’ journey encapsulates one of my life’s driving forces: being a publicly doubted underdog and emphatically proving every single doubter wrong.

The classic startup version of this challenge is the company that, after endless pitching with few investors, suddenly has a fundraising round that everyone wants to join.

For those of you who don’t know, before embracing my venture capital nerd side, I used to coach non-scholarship college football, and I loved it. I enjoyed the camaraderie, the pageantry, the thrill of victory, and the motivating drive of defeat.

I also loved being the underdog.

There’s a special feeling in knowing the other team thinks they will roll over you. Only you know you are going to give them the game of their lives—something I will never forget.

Right now, college football fans across America (Miami fans excluded) get to enjoy the same feeling as the Indiana Hoosiers.

Indiana managed to actually accomplish the overused moniker “From worst to first.”

As if that isn’t enough of an underdog tale, they are led by coach Curt Cignetti, who came from lower level James Madison. My hometown Cincinnati Bearcats allegedly refused to interview him for their head coaching job. They felt he lacked big-program experience (shakes fist at the sky).

The Question I Get Asked

Indiana’s championship run crystallized why the underdog journey resonates with me and shapes my professional path. With this in mind, I can now clearly answer a question I’m often asked:

Of course, working with startups comes with its own set of challenges (to my clients: you can laugh while reading these—there is no need to apologize):

• Many problems are urgent and require immediate attention.

• Clients need enough money to stay in operation while also paying for your services.

• Overly eager clients may agree to something without consulting you first.

• Members of the same company will fight with no formalized way to solve that argument (leaving me to play therapist).

Why I Keep Coming Back

Yet, despite all these challenges, something keeps pulling me back into startup land.

I love supporting the underdog. Backing those who other doubt gets me excited to open my laptop every day. However, I embrace the underdog role even more by representing startups and fund managers in the Midwest, an underdog region in the startup and venture capital scene.

My love of the underdog does not stem from watching too many movies with fairy-tale endings. Instead, my disability has given me the opportunity to play the underestimated underdog throughout my life.

“You’re never going to be able to walk.”

“You should stop working out so much and enjoy the wheelchair.”

“You should just be happy to get a job—perhaps a cashier is a good career for you.”

“Are you sure law school is for people like you? Don’t they have special schools?”

“How are you going to get clients if you’re in a wheelchair?”

These are just some of the common refrains I have heard throughout my days.

When I was younger, such statements got me down. Now, I meet them with an external smile and an internal smirk. It’s another chance to prove someone wrong who underestimated me.

Wear Out or Rust Out

A personal mantra guides me: “Wear Out or Rust Out.”

It reminds me to use skeptics’ doubts as motivation. You either let them lull you into non-action and rust out, or you use their doubt as fuel and keep working so that you only stop from wearing out.

I hope anyone reading this will find their own mantra. Use doubt as a stepping stone, not a stumbling block.

The Final Chapter

This opportunity to help others prove doubters wrong by supporting underestimated founders is exactly what drew me into working with startups and venture capital.

Indiana’s title journey serves as an example of what I shout from the mountaintops:

The doubters don’t get to write the final chapter.

The odds do not determine the outcome.

If you’re building something you’re passionate about, or if you’ve been told your idea won’t work, or you keep hearing that your background isn’t right, welcome to the club. You’re the underdog everyone is betting against!

Let’s Go!

That club is exactly where I want to be. Because the best stories in startup land, just like in college football, aren’t written by the powerhouses. They’re written by the people everyone underestimated who refused to believe them.