Greg Raiten

Co-Founder of The Suite | Building communities for executives

[Greg Raiten @gregraiten]

A standout GC can flip between two roles - general practitioner and surgeon.

The key is knowing which hat to wear, and when.

↳ General Practitioner Mode

Most legal questions that land on your plate aren’t emergencies. They’re checkups and routine care, such as drafting standard contracts, keeping up with compliance, and scanning for low-level risks.

As the GP, your job is to move fast and keep the business running smoothly without tying anyone in legal knots. The stakes aren’t high enough for endless debates, so you need to act quickly and try to head-off any potential issues early.

The secret is to build genuine trust with your internal teams. If you show up as a proactive advisor - offering timely, pragmatic guidance - you’ll set a collaborative tone that helps everyone operate with more confidence.

↳ Surgeon Mode

Every so often, a startup faces a make-or-break moment - like a tough lawsuit, government scrutiny, a high-stakes M&A, or something else that has the potential to alter the business's trajectory.

In these company-defining moments, you need to shift from GP to surgeon. Gather all the facts, sharpen your specialist skills, and make well-informed and decisive calls. When the stakes are existential, you need to slow down a bit, set a clear plan, and act with precision.

One of the common mistakes I see newer GCs make is staying stuck in surgeon mode. They treat every small question like it’s a code-red crisis - over-investing time, energy, and resources on routine stuff with low risk. In the process, they wind up slowing down the entire organization and diluting the impact of the moments that really do warrant a carefully deliberated response.

If everything’s an emergency, then nothing’s truly urgent. As a GC, you need to develop a strong barometer to know which is which.

[Greg Raiten @gregraiten]

A core challenge for any GC in a fast-growing startup is switching vantage points.

You can’t stay stuck in the contracts, and you can’t live exclusively in the strategy either.

It’s important to operate across the full spectrum to effectively do your job, and the trick is knowing when to drop down and when to climb back up.

1️⃣ 100-Foot View

This is execution mode. Drafting contracts, fielding compliance questions, etc. Everything that keeps the day-to-day machine humming. Solo-GCs or those with small teams typically need to spend a disproportionate amount of time here. You want to develop solid processes to prevent legal bottlenecks and scale yourself and your department over time.

2️⃣ 1,000-Foot View

This is your cross-functional lens, where focus shifts to how legal intersects with every other team (e.g., HR, sales, product, finance, and beyond) to drive the business forward. What are the company and departmental goals that legal can help accelerate? Where can you be proactive instead of reactive in advancing the ball? This is where most GCs should be aiming to spend most of their time..

3️⃣ 10,000-Foot View

This is where you think long term. Scan the horizon for looming regulatory shifts, consider how future expansion plans might impact your legal strategy, align with your executive team on the big rocks. Given the nature of legal as a support function, it’s all too easy to get stuck in the Important & Urgent quadrant of the Eisenhower Matrix (especially as a solo-GC). But it’s critical to carve out time to think strategically (Important & Not Urgent) and identify opportunities for legal to add offensive (vs. defensive) value.

The real value you bring as GC is being able to move seamlessly between these three perspectives by spotting risks early, enabling other teams to move fast, and making sure you’re steering the company in the right legal direction over the long haul. Keep these altitudes in balance, and you’ll be indispensable.

[Greg Raiten @gregraiten]

Startups love talking about “technical debt” - the engineering shortcuts you take to move fast, knowing you’ll have to clean them up later. But there’s a twin threat that often flies under the radar - legal debt.

In most cases, legal debt is just a hassle you’ll have to invest some time and resources into fixing down the road. But sometimes, legal debt can explode into a very costly - possibly even existential - nightmare.

I generally think about it in three main buckets:

1/ Operational Debt

From the way you hire and fire to commission plans to board governance - good corporate hygiene is important. Cut corners here and you risk not just employment disputes, but also headaches in diligence or an IPO where a messy cap table or dysfunctional board structure can slow down a deal. Use vetted forms and processes, train your leaders, and adopt a solid governance framework to help minimize this debt from accumulating.

2/ Contractual Debt

Sloppy deals or handshake agreements might seem quick and easy at first. But once you start scaling, those vague clauses or missing risk limiters can really come back to bite you. The fix? Use templates that are appropriate to the stage, identify the risks for the stakeholders involved to make sure everyone is comfortable, and also note the gaps that you may want to fill in later if things go well. Keep a tidy contract repository and do periodic checkups on the terms that matter.

3/ Regulatory Debt

Cutting regulatory corners to get to market faster might seem like a competitive advantage until you’re dealing with fines, stalled approvals, or a call from a regulator. As the lawyer in the room, you really need to exercise your judgment here because sometimes it may actually be worth the risk to ask for forgiveness and not permission. Build trusted relationships with specialized counsel, track regulatory shifts, and deeply understand the ramifications of what’s at stake. This is one of the areas that could kill your company or possibly even land you or others in jail if you’re not careful.

Of course, not all legal shortcuts are bad. Every company takes some shortcuts to fuel growth. But keep an eye on the “interest rate,” which is the real cost of ignoring legal risks. Have a plan to pay it down as you scale, or you’ll find yourself buried under a mountain of debt at the worst possible time.

[Greg Raiten @gregraiten]

When you’re a solo GC, that first hire on your team can be a real boon.

But I’ve seen first-time GCs struggle to scope the role properly for maximum value.

Do you want to hire a generalist or specialist? If a specialist, what kind? Or perhaps you don’t need a lawyer at all and would do better with a legal ops professional or a paralegal?

The key is to get clear on why you’re hiring and what success looks like six, nine, or twelve months in.

Do you need someone to free up your bandwidth so you can focus on something else? A generalist with broad skills may be best.

Maybe you just need to handle more volume? Consider a dedicated commercial counsel.

Perhaps the business has grown in a way that necessitates deep knowledge in a particular area (e.g., privacy, regulatory, IP, etc.)? Then, you probably want to bring on a specialist sooner rather than later.

Or is it possible that you need someone to bring processes, tools, reporting, or similar to your department so you can move faster? That’s where legal ops shine.

In most cases, complementary strengths are key. It’s tempting sometimes to hire a “mini-me” who thinks, works, and solves problems like you do. But that usually doesn’t take you or your company too far.

So, what was your first in-house legal hire? Would you do it the same way again?

[Greg Raiten @gregraiten]

A lot of lawyers go into negotiations trying to "win.".

It makes sense in theory - we all want to get the best possible terms for “our side.”

But if you're in-house at a company, you need to keep the bigger picture in mind. That means understanding when a contract is (hopefully) just a prelude to a long and fruitful relationship.

I've seen deals mushroom unnecessarily or ultimately even die over minor terms that didn't actually matter in the long run. I've also seen teams get so focused on winning the small battles that they damage the long-term partnership before it has even really started.

In the end, what matters is getting to the right outcome for the business at large. And that usually means landing at a place where both sides feel satisfied (enough) and are excited to embark on a mutually-beneficial partnership.

So before you dig in on that point in your next contract negotiation, ask yourself:

* Is this a must-have or a nice-to-have?
* How much does this matter to the other side?
* How much does this really matter to us? For example, will it matter in a year? What is the magnitude of the risk and how likely is it to occur?
* Will digging in on this point erode trust?

It can be tempting to negotiate it all, especially when you feel like you have the better argument. I’ve been there and done that myself too many times.

But in most cases, the best negotiation tactic is to let go of the small stuff to win the big picture.

[Greg Raiten @gregraiten]

The word “general” in General Counsel is what makes it a uniquely special position.

It means your role is horizontal, supporting a wide variety of legal challenges across your organization.

It means your scope is a mile wide, forcing you to become a jack/jill of all areas and a master of a few.

It means you’ll learn the secrets of every department.

It’s not stated in the job description, but being an effective GC turns you into one of your business’s key insiders.

That’s because legal issues appear in finance, marketing, product, HR… really wherever regulations meet people.

Since confidentiality is baked into the role, colleagues often trust you with their “secret” problems.

From this vantage point, you can spot patterns, risks, and opportunities nobody sees. You can use that perspective to become a strategic asset to your colleagues and your business.

You build trust by handling each issue with empathy and discretion. You build credibility by providing business-savvy advice that balances risk and opportunity.

And the more you do both of these things, the more integrated you become and the more likely your colleagues will approach you early and often.

It’s a powerful flywheel that makes being a GC an incredibly rewarding - and highly versatile - career path.

[Greg Raiten @gregraiten]

There’s a running joke that lawyers only show up to tell you everything that might go wrong.

This stereotype creates the illusion of two distinct cultures under one roof:

➡️ Legal, stuck on risk-spotting
➡️ Business, focused on growth

We talk about bridging this gap as if it’s a subtle art, but it’s really about showing the business team you’re just as excited about product-market fit as they are.

As an in-house counsel, you can do that by showing real curiosity about the business model. Rather than waiting for a new contract to land on your desk, you can ask things like, “How does this product stand out? Who’s our customer persona? Where do we see ourselves next year?”

This shows the product / engineering teams that your legal guidance is grounded in a deeper understanding of the company’s goals.

On the flip side, invite key business folks to a quick “legal basics” session. Maybe share a concise list of common contract pitfalls or a cheat sheet for marketing disclaimers.

When the business side realizes you’re genuinely invested in their success, they’ll stop viewing you as an obstacle.

If you only speak up when things are on fire, you’ll always be seen as a crisis manager.

[Greg Raiten @gregraiten]

There are pros and cons to being a fully remote company.

One of the obvious cons is that you don’t get to spend much time together in person, and there’s an unmistakable energy that only forms when people share the same physical space.

That’s why every year, we pick one location, fly everyone in, and spend a few days together bonding as a team.

This year we were in Cabo, and Alyson, Krisi, Maria and Julia really knocked it out of the park planning an incredible event with the right balance of work and play.

They created ample space for the team to build deeper connections, tackle some exciting challenges together, and generally just have a ton of fun (ziplining, whale watching, cooking classes, a sound bath, lots of great meals, etc.).

The theme of this year’s offsite was “Unreasonable Hospitality” (inspired by Will Guidara's book), and we spent a lot of time talking about how we can incorporate this powerful principle in everything we do for our members, our partners, and our colleagues.

I was blown away by the creativity, passion, and talent of the team. From bringing our guiding principles to life through short films and superhero squads, to building innovative prototypes using cutting-edge AI tools during our company-wide hackathon - the energy and ideation were off the charts.

I guess it shouldn't be a surprise, though—we're fortunate to have a team of some of the best community builders in the world!

It might sound a little cheesy, but I truly believe this:

It takes a community to build a community. And the team at The Suite is an extraordinary community to be a part of.

[Greg Raiten @gregraiten]

Today we announced @thelsuite_co 's second strategic acquisition - a popular streaming platform for Continuing Legal Education (CLE) content called @luminateplus.

Think of it as a Netflix-style eLearning experience for legal professionals, complete with a modern web/mobile app and personalized content suggestions that will improve the more you use the product.

As lawyers ourselves, we know that it can be a real struggle to find high-quality CLE content when and where you need it. If you want that content to be practical and relevant to your day-to-day, it’s even harder, especially when talking about the elusive specialty credits that many jurisdictions require. On top of all that, it’s surprisingly expensive if you need an on-demand solution, particularly for teams.

We don’t think it should be that difficult or that expensive, so we decided to do something about it. With Luminate+, we hope to elevate the continuing legal education experience, delivering a comprehensive library of on-demand CLE content led by some of the top law firms and GCs in the world. Luminate+ content is interesting, useful in your practice, easily accessible, and affordable.

And the best part is that this new product enables us to reach and support the entire legal industry - whether you’re an L Suite member or not, an in-house attorney or at a law firm, government agency, non-profit, etc.

All L Suite members now have access to Luminate+ at no extra cost via SSO directly from the member platform. Luminate+ is also available as a standalone subscription (individual or enterprise) for all 1.3M lawyers in the United States.

I’m also thrilled that Andrew Dick, Founder and CEO of Luminate+, has joined The L Suite team! We already have some exciting new initiatives in the works that I can’t wait to share, but more on that for another day.

For now, here’s to a future where CLE is no longer just a last-minute scramble to check-the-box, but a useful, actionable tool to support your legal practice!

[Greg Raiten @gregraiten]

@thelsuite_co Full press release: https://t.co/6WCz4d5EUz

[Greg Raiten @gregraiten]

We made a big announcement today at @thelsuite_co - our first acquisition! 🎉

LINK (Legal Innovators Network) - the industry-leading community for senior legal ops professionals co-founded by the incredible duo Stephanie Corey and Andrew Dick - is now officially part of The L Suite family.

Legal ops has become a fundamental part of the modern corporate legal department. These are the folks who run the “business” of your in-house legal team - streamlining and optimizing the legal department with advanced tools and efficient processes, and managing everything from software evaluation/implementation to contract workflows to outside counsel spend.

In more mature organizations, legal ops leaders are critical partners to the GC and the entire in-house legal team. At earlier-stage startups, the GC or one of their deputies is probably filling the role themselves.

In either case, legal ops is a distinct skillset with a unique set of responsibilities. And like any other group of senior professionals, these individuals can greatly benefit from a curated community of peers.

By bringing LINK into The L Suite, we’re taking a huge step towards realizing our ultimate vision - creating the most impactful community platform for in-house legal professionals, enabling them to push their companies ahead of the curve with smarter, faster decision-making.

This is one of those rare win-win-win situations. LINK members get access to a world-class community and resources, with an enhanced event line-up and a cutting-edge member platform. L Suite members get a dedicated membership tier for their legal ops colleagues, and they all get
access to an entirely new set of legal ops programming. And legal tech vendors are able to better support and build value-add relationships with the entire ecosystem, showcasing their thought-leadership and engaging in practical discussions with both GCs and legal ops leaders in a single forum.

It’s the coveted trifecta, and it’s now a reality. Please join me in welcoming LINK to The L Suite family!

Oh and watch this space for another big L Suite announcement next week…

[Greg Raiten @gregraiten]

@thelsuite_co Become a LINK member: https://t.co/WRhaU9pLc4.

[Greg Raiten @gregraiten]

https://t.co/2UJMlHoA6x

[Greg Raiten @gregraiten]

It’s a great feeling when you get a check from an investment you made. Whether you’re an employee investing your time and effort at a startup, or you’re an investor investing your capital.

That’s the driving force behind the startup ecosystem - an eventual exit in the form of some sort of liquidity event.

And for the lucky few companies (and their investors) that do achieve a liquidity event, it may manifest in a variety of different forms.

If you’re a GC, you must be ready to execute whichever exit opportunity comes your way.

Especially in markets like this, where:

- Investments (in the form of sweat equity or dollars) are long in the tooth,

- Market dynamics have made certain common exit pathways more complicated (due to untenable valuations, ‘dirty’ cap table structures, etc.) or essentially closed them for the time being (IPOs), and

- A variety of competing interests (like VC fund dynamics) and regulatory realities (e.g., equity plan tax rules, securities rules, etc.) may nonetheless be forcing your hand towards action now rather than later.

That’s why I’m particularly excited for our inaugural 𝗟𝗶𝗾𝘂𝗶𝗱𝗶𝘁𝘆 𝗦𝘂𝗺𝗺𝗶𝘁 𝗼𝗻 𝗙𝗲𝗯 𝟭𝟭-𝟭𝟮 𝗮𝘁 𝘁𝗵𝗲 𝗡𝗬𝗦𝗘 (link in the comments). This is such a complex and multifaceted topic, and it’s also an area where a well-prepared GC can really shine.

We’ll be diving deep into all the common exit/liquidity structures - buy-side M&A, sell-side M&A, take privates, IPOs, dual-track processes, SPACs, tender offers/secondaries, etc.

We’ll talk about the complexities of different forms of consideration in M&A deals (cash, private/public stock, debt), and we’ll explore the nuances of selling to different types of buyers (strategic vs. PE).

There’s a lot to unpack here, and if you’re a GC of any type (startup, public company, venture fund, PE fund) with any potential liquidity event on the horizon - you probably don’t want to miss this one.

Not yet an L Suite member? You can apply at @thelsuite_co to join us (our events are for members only, and free).

I have no doubt it will be a rich set of conversations ;)

[Greg Raiten @gregraiten]

Great GCs build bridges.

They marry business goals with legal realities, finding solutions and pathways to achieve the desired outcomes.

The connect cross-functional initiatives, ensuring the legal processes are in place for teams to move forward with clarity and confidence.

And often, they fill in the gaps at the executive leadership level, absorbing operational necessities that don’t have a clear owner.

So how do the best ones do it so effectively?

It starts with forming a deep understanding - of the company’s business model and goals, and of each underlying team and how their initiatives ladder up.

Join a sales meeting to learn their pipeline strategy. Review a product roadmap to see which features are the priority.

The more you grasp your company’s and colleagues’ challenges and objectives, the more effectively you can offer legal solutions tailored to their needs.

And when you’re designing those legal solutions, remember that momentum is everything in a startup. That doesn’t mean you should skip the essentials, but you should focus on building “minimum viable” legal frameworks wherever possible.

No one wants the “no” lawyer, or the “overly complicated” lawyer. Position yourself as a problem-solver. Proactively flag risks while at the same time providing alternative paths forward.

When teams see you as someone who facilitates rather than obstructs, they’ll start coming to you early (and often).

A strong bridge holds up under pressure and allows everyone to cross safely. And when you’ve done it right, the company moves faster, risks are reduced, and every team feels supported.

[Greg Raiten @gregraiten]

I used to think it was bad to say “I don’t know.”

Like many young GCs, I thought my value came from having the answers. I worried that if I didn’t have the answers offhand, it would look like a failure and my boss would start wondering if I was the right person for the job.

It’s hard to admit you don’t know in front of your CEO or your board. I suspect this may be especially true for lawyers, as we’re trained to reduce uncertainty, foresee risks, and project confidence. We’re supposed to be the experts in the room on all things legal.

But over the years, I learned that being an expert doesn’t mean having all the answers. In many ways, it’s actually the opposite - it’s knowing what you do and don’t know, having the confidence to embrace your gaps, and (perhaps most importantly) mastering the ability to get the answers.

Don’t be afraid to say “I don’t know.” It shows self-awareness and builds trust with your colleagues. Just make sure to follow it up with “...but I’ll dig into this and get back to you.”

[Greg Raiten @gregraiten]

One of the hardest things about being a GC is that you’re rarely the decision-maker, but you’re always part of the decision.

Early in my career, I thought my job was to give the “right” answer. But at a startup, decisions are rarely that clean. They typically involve trade-offs, competing priorities, and incomplete information.

Effective decision-making / advising as a GC means understanding a few different layers of analysis.

1/ Legal Analysis

What does the law say? What are the risks and constraints? Your job here is to translate legal complexities into actionable insights. “Here’s what’s permissible, and here’s what’s risky.” This layer is the foundation where lawyers generally feel most comfortable, but it’s not the whole picture.

2/ Business Application

How does this decision align with the company’s goals? What’s the upside? What’s the opportunity cost? For example, you might advise that pursuing a particular deal is high risk but could open a new market. This is the layer where many new in-house counsel struggle as it may not have been part of their thought process when they were outside counsel.

3/ Practical Grounding

What’s practical given the time, resources, and stakeholders involved? A legally sound plan that’s impossible to execute is no better than no plan at all. This layer is where you factor in constraints like bandwidth, urgency, or relationships. There’s no magic here, but every leader on the team should be grounded in reality.

The goal with this framework is balancing precision with practicality. Instead of overwhelming people with every legal angle, guide them through the layers so they can make informed, risk-adjusted decisions.

At its core, good counsel is about bringing clarity to a world full of noise.

[Greg Raiten @gregraiten]

Many big opportunities in my career started with a small introduction.

Just one person saying, “You two should talk.”

And now that I’m leading a community company, I see it everyday - how much of our success relies on this simple act.

Connections really drive do drive most things.

Whether it’s meeting a peer or expert advisor that can help you navigate a live challenge, or a leader that becomes your next boss, or just a new person that turns into a lifelong friend.

An introduction that feels small to you might change everything for someone else.

When you take the time to really understand someone’s goals, interests, strengths, and challenges, you start to see opportunities they might not see themselves.

So next time you have the chance, make that introduction. Take five minutes to connect two people who might help each other, and do it without expecting anything in return.

It’s simple, and it’s powerful. And it just might be exactly what they didn’t know they needed.

[Greg Raiten @gregraiten]

The worst surprises are the ones you could have seen coming.

But risks don’t always show up with flashing lights. They hide in the corners of fast-moving projects, ambitious goals, and unclear responsibilities.

As a GC in particular, you need to be proactive about identifying risks across the company. Because if you’re just waiting for someone to bring you a problem, you’re asking to be blindsided.

Here are a few tips I picked up in my GC/founder journey:

1. Listen for Ambiguity

Words like “I think,” “maybe,” or “it should be fine” should set off alarm bells. If people can’t confidently explain how a decision aligns with legal or operational guardrails, it’s time to dig deeper. The best way to prevent ambiguity and make sure there is alignment is to ask clarifying questions: “Who owns this decision?” “What’s the fallback plan?” “Are we sure this fits within X framework?”

2. Watch for Unusual Silence

When people stop talking about a project, it’s easy to assume everything is on track. But sometimes, silence means trouble. A lack of updates can signal discomfort, confusion, or unresolved issues. If a team suddenly goes quiet on something critical, make it a point to reach out and ask, “How’s everything going here?”

3. Track Repeated Patterns

If you keep hearing the same issues pop up across different teams or projects, it often points to a bigger systemic problem. Maybe it’s a gap in training, unclear policies, or a structural weakness in how decisions are made. Depending on what the issues are, it may be worth proactively investing the time to fix the root cause now rather than reactively spending time dealing with the fallout in the future.

The earlier you catch a problem, the smaller and easier it is to fix. Miss it, and it grows. Over time, spotting these patterns becomes second nature.

When you’re the person who can say, “I think there’s an issue here” before anyone else sees it, you build trust across the company. When you can add on, “And here’s the solution…”, you build a 🚀 career.