How to Communicate Direction

The most important job of any leader is to communicate the direction.

When you’re just starting out, communicating direction is easy. You’re in the room with every decision. You’re talking directly to the whole team every day. Everyone knows where you’re headed because you’ve said it ten times that week.

But as your company or team grows, alignment gets harder. New teams form, the existing team scales. Middle managers step into leadership roles. Context gets lost, and the clarity that once felt easy starts to fade.

This is where many teams get misaligned and start rowing in different directions, not because the direction isn’t strong, but because they stop communicating it well (or because some team members disagree, which is a whole other topic). It doesn’t matter how coherent or strong your direction is if you fail to convey it across the whole team.

What is “the Direction”?

Great question. This is not the grand Vision Statement on your website. It is the direction you are all headed right now. This can be the current goal or the vision for the product or any information that is critical for the team to make decisions and do their job.

1. Communicate the Direction Consistently

If you want everyone to move in the same direction, your deputies need to be just as clear on the vision as you are.

When you're consistent, your leaders can reinforce and cascade that message. Without that consistency, the direction starts to splinter, every team creates their own slightly different version, and alignment breaks down.

Tip: Use the same language. Don’t “reframe” the direction for different audiences or teams. You want everyone from leadership to ICs to be using the same words and phrases when they describe where the company is going.

2. Communicate the Direction Constantly

Repetition is critical.
By the time you’re tired of saying the direction out loud, some people on your team are just hearing it for the first time.

You need to repeat the direction daily, weekly, monthly, not because people are forgetful, but because you need to hit an effective frequency for people to remember. On top of that, new employees join, teams shift, perspectives change. Repetition keeps the message top of mind and actionable.

Tip: Tie everyday decisions back to the direction. Show how priorities, resourcing, and even what you say “no” to are guided by the direction. Make sure everyone understands why this is the direction.

3. Communicate the Direction Across Many Channels

Different people absorb information in different ways.
Some need to see it in a deck. Others need to hear it in a meeting. Others need to read it in an email.

That’s why you need to use all hands, written updates, standups, and any other chance you get to reinforce the message. The best leaders don’t just say it once they relentlessly reinforce the direction.

Tip: Don’t worry about being repetitive across formats. Being redundant across channels is a feature, not a bug.

When the Vision Changes

As your company grows, so will your understanding of the market, your customers, and your product. That means the direction will evolve.

If the direction changes, say so clearly and explicitly.

Explain:

• What changed

• Why it changed

• How it impacts current work, teams, and goals

Nothing breaks trust faster than pretending the direction didn’t shift. Your team is smart, they’ll notice. If you don’t name the change, they’ll fill in the blanks with rumors and assumptions.

Tip: Use direction changes as a pause. Take a moment to lift everyone’s heads up out of the weeds and reset. Often direction change can benefit from a stop of momentum to restart again on the new path.

Final Thoughts

If someone on your team is asked where the company is going and why, they should be able to answer without hesitation. They should be able to use this information to inform the tactical decisions in their daily work.

I have found that as a team scales more effort needs to be put into constantly communicating direction. Leadership is responsible for making sure the resources on the team are being applied in the most important areas. The best way to do that is to share the current direction clearly, consistently, constantly, and across every channel.

Minimum Viable Culture

Startups live or die by focus. In the early stages, it’s easy to convince yourself that “culture” is something you’ll figure out later: after the product launches, after the next round closes, after you hire just a few more people.

But culture happens by design or by default. It starts forming the moment your team does.

I have seen early-stage companies ignore culture entirely, only to wake up months later with a team dynamic they do not recognize. I have also seen founders overengineer their culture docs, wasting time on broad generic ideas and marketing language that never impacts day-to-day work.

This post outlines the essential elements of culture every startup should define.

What Is Minimum Viable Culture?

Minimum Viable Culture (MVC) is the smallest set of cultural foundations that every startup should define early and update often. These foundations don’t require offsites or consultants. They require honest discussion and the willingness to write down what actually matters.

MVC is the minimum viable set of documents (or leadership discussions) that help your team act faster, communicate better, and stay aligned as you grow.

They should be short, actionable, and revisited every 6–12 months or whenever a major change reshapes your company. Think of MVC as a lightweight scaffolding for your culture, just enough structure to keep you focused, without slowing you down.

Here are the four components every early-stage startup needs:

1. Mission & Vision

Why does your company exist?

Your mission answers what you can be the best in the world at. Your vision is what you aspire to become in success.These two ideas help your team make decisions on what you will or won’t focus on and tell a compelling story to future employees, partners, and customers.

Read: Why Does Your Company Exist?

2. Core Values

What behaviors are expected or prohibited?

Your values should help employees make daily decisions. They should be specific enough to be lived, not just stated. They define what good looks like and where the line is when something needs to be addressed.

Read: Why Every Company Needs Core Values 

Read: How to Write Your Company’s Core Values 

Read more with these examples from Proletariat:

• Understand Why

• Decide Fast and Iterate

• Take Responsibility

• Exceed Expectations

• Be Respectful 

3. Cultural Communication Guide

How do we work and communicate as a team?

Every team has unspoken norms and this document will make them explicit. Your communication guide should cover how you give feedback, make decisions, run meetings, and use tools like Slack or email. It promotes clarity, reduces drama, and speeds up onboarding.

Read: Culture Communication Guide 

4. Compensation Guide

How do you reward and incentivize the team?

Be explicit about your philosophy on salary, equity, titles, promotions, bonuses, and PTO. Even a one-pager makes a difference in making thoughtful choices on decisions that are difficult to reverse.
Read: How to Write a Compensation Guide for Your Startup 

Final Thoughts

One of the most important roles of any leader is allocating resources. Minimum Viable Culture is meant to establish the highest impact cultural tools with the smallest investment footprint.

Take the time to have these discussions and do the work to record the output. A focused leadership team could cover all of this ground in a single day offsite with the proper preparation and research.

Don’t spend too much time making everything perfect, just be ready to iterate. These documents will evolve, just like your company. That’s the point. But getting them in place early will give you a cultural foundation that scales.

Why Does Your Company Exist?

Every company or team should have a mission they are driving towards and an aspirational vision for who they will become if successful. But too often, vision and mission statements are treated like branding artifacts or website filler; impractal, lofty, and ultimately useless.

At Proletariat, we crafted a mission and vision that were practical, grounded, and designed to be useful every day. They shaped how we hired, how we prioritized, and how we built culture.

In this post, I’ll share the mission and vision we used at Proletariat, why we wrote them the way we did, and how you can write statements that actually help your team make better decisions.

Proletariat’s Mission and Vision

Mission Statement

To create innovative experiences with rich IP at the frontier of entertainment.

Vision Statement

To become a beloved game studio with a diverse team doing our best work for our players.

Mission vs. Vision: What is the difference and why do they matter?

You’ll find dozens of definitions online (including unhelpful ones from Wikipedia), but here’s how I break it down:

• Mission: What can we be the best in the world at?
  This is about what you uniquely do better than anyone else. It clarifies your competitive edge and core focus. It explains what your company and team will do, and more importantly, what you will not do. What dent do you want to make in the universe?

• Vision: Who do we become if we’re successful?
  This is about aspiration. It should inspire your team and guide your culture into building something bigger and better. What do you and the universe look like with that new dent? 

Every decision made within the organization should be in service of progressing the mission to accomplish the vision. 

How We Applied Them

The word choices in these statements were deliberate. For the mission it reinforced the type of work we did:

• "Innovative experiences" led us to be innovative in gameplay, storytelling, art style and more. It prioritized originality and pushing the boundaries of genre conventions. It also meant we would not pursue fast follows or red oceans.

• "Rich IP" encouraged us to think beyond mechanics and product to create meaningful worlds that would resonate with our players.

• “Frontier of entertainment” drove us towards emerging platforms, new ways to build community, and to invent new go to market strategies.

For the vision it shaped our values and inspired us into becoming something better:

• "Beloved studio" reminded us that trust, respect, and radical candor mattered, especially in how we supported our team, our players, and our industry.

• “Diverse team” shaped everything from how we approached hiring to how we ran our development process to who was included in our meetings.

• "Best work” meant making tradeoffs to ensure the team could be proud of the work they were doing both individually and as a team. That could mean anything from providing important resources to protecting time for polish.

• “Our players" kept the focus on the community because without them we could not be successful.

What made them work

To make these statements stick we considered some key areas:

• They were specific. We chose the words carefully to have a strong perspective that we felt uniquely fit the company we wanted to build. The broader your mission and vision statement, the less valuable they will become in defining your company or team.

• They were actionable. These statements were each meant to answer a single question that would impact the daily work of the team.

• We used them to make real decisions. If your mission and vision don’t help you make hard decisions, they’re not doing their job.

• They connected to our values. Each value reinforced the path to our mission and the behavior needed to achieve the vision.

Final Thoughts

A strong mission and vision aren’t just for pitch decks or website About pages, they’re daily tools to guide decisions, align teams, and inspire action. Done well, they help your company focus on what matters most. A great mission grounds your work in what you can do better than anyone else. A great vision points toward who you want to become.

You don’t need to craft the perfect statement on day one, but you do need to commit to defining and refining it as you grow. Your mission and vision should evolve with the company, but they should never be meaningless. When used well, they become rallying cries for your team and magnets for the people who believe what you believe.

If your team doesn’t know why the company exists or where it’s going, you can and should fix that.

How to Write a Compensation Guide for Your Startup

Every company has a compensation philosophy, even if they haven’t written it down yet.

How you pay people, what you reward, and what you don’t reward sends a powerful message about your company culture. There are no right or wrong answers to these questions, but these decisions shape your culture just as much as a cultural communication guide or core values. 

We never formalized this into a document at Proletariat but we did discuss it regularly at the leadership level. I think having a streamlined document would have made it easier for us to review and revisit this topic as we grew.

In this post, I’ll break down the key areas of compensation philosophy and how each one impacts company culture.

1. Cash Compensation

This decision will impact recruiting and retention of the team directly. It is worth discussing several different topics on the leadership level because nearly everyone that joins the team will need a salary. Consider the following questions:

• Should cash compensation be a major motivator for talent to join our team? Most start up companies shy away from this because every dollar spent on salary is one less dollar of runway, but every company is different, so what makes sense for your company in your market is your call.

• Do we want to compete with top of market cash compensation? Is it required to secure talent in certain roles? Paying top of market for some roles and not others can be messy but is also maybe worth it to get the talent you need.

• If we pay mid-market or below, how will we attract and motivate talent that is currently being paid more? Being clear about what you offer beside cash as part of a compensation plan like this is critical to attracting talent.

• What if someone wants way below market salary in exchange for more equity? More on this in the equity section, but this is an example of how compensation is often quite unique to the individual and you should be prepared to find solutions.

• Should we pay differently based on region (if the team is distributed)? This decision could lead to incentives for people to move to certain areas.

2. Vacation and PTO

How your company approaches time off is important because it impacts the way people work but more importantly it can often impact their family. This goes beyond saying “we have unlimited PTO” because the details here really matter. Consider the following questions:

• What policy is the best for us? The amount of time you give, how it is accrued, and how it can be used are all very important. 

• What holidays do we provide? Choosing certain days can make things easier or harder on people with families or those of certain religions, not to mention if you have a distributed team.

• How are vacations approved? How flexible do we want to be with employees? This speaks to areas like trust and communication. It is worth figuring out under what circumstances vacation would not be approved and how you manage that.

• If people crunch to hit a major deadline do we reward them with comp time? Every team would love to have great work-life balance but it is good to have a plan for when you don’t. If you don’t provide comp time do you provide overtime? Or a bonus? Establishing this before you need it will make it easier to implement.

3. Titles

Titles are an interesting challenge at startups because it is often impossible to make them reflect the roles and responsibilities on a small team. However, changing titles later can be very painful as many people come to identify with their title. Consider the following questions:

• Do we want titles to be seen as a reward or motivator at the company? If titles are used regularly, like saying “this needs a senior engineer on it” it will indicate to teammates that titles matter. That may be unintentional and the title may be shorthand but that is what will occur. Where and how titles are used throughout the organization will motivate the team in different ways.

• Will titles reflect role, seniority, hierarchy, or anything else? There are many ways to handle titles, and how you construct them and then explain to people why they have a certain title will change how they behave.

• How do we communicate titles to external partners? Titles are used as a tool to give context to people both within the organization and outside of it. Some titles are required, like many investors would feel uncomfortable if no one at the company had the title of CEO. How titles are used externally communicates more than just what the individual does on the team, so it is important to consider.

4. Bonuses

It is generally tricky to create a bonus plan because bonuses are often best used as well… bonus. However, knowing when you would want to pay a bonus and more importantly, setting clear expectations with your team, is critical. Consider the following questions:

• Do we want to pay a yearly bonus? If so, how will that be structured? Choosing to do this on merit or tenure or team performance will change the behavior of the team. I generally do not like yearly bonuses because they set up complicated expectations and rarely have the intended effect.

• Will we pay signing bonuses? This goes back to some of the questions about cash comp and attracting talent. How this is handled will be one of the first data points a new employee will have about the culture.

• Are there any other cash bonuses or profit sharing we want to include? There are all sorts of bonuses and incentives that exist across industries. How this factors into overall compensation can be a major motivator for new talent to join or how existing team members behave.

5. Equity

One of the biggest reasons people may choose to join a startup at the early stages is to get equity. Due to the long time horizon on most vesting it is very important to not just wing it. Consider the following questions:

• Who gets equity and how much do they get? If you do only one thing from this post, please have this discussion with your leadership team. Do not start giving out equity without a thoughtful plan because equity is your most valuable resource.

• How often will you provide additional equity? Most equity programs vest over 4 years and are used as a strong incentive to stay at the company. It is important to figure out what to do with people who have fully vested but also how you can incentivize great performers with more equity along the way.

6. Promotions

Promotions touch every area of compensation: cash, equity, title, and more. It can be a deep rabbit hole that opens up questions about career ladders, performance management, all sorts of other critical human resource areas that are likely not a priority for an early unprofitable start up. Consider the following questions:

• How does someone get promoted? The process for this could be simple or incredibly detailed, but it is worth talking about before the need arises so individuals and managers know information like who is needed to approve and documentation they need to do it.

• When someone is promoted what forms of compensation do you provide? As mentioned in the equity and title sections, there are many ways to do this. Are there certain types of compensation that is required to give with a promotion (like a title change) and are there others that are never given (like equity)?

• When do we do promotions? Is it tied to performance reviews? Choosing to promote on a cycle or when needed matters. If employees know they will only be promoted with a certain window it can alter behavior. It is totally fine to have plans for both regular promotions on a schedule and off-cycle promotions when the circumstances call for it.

• Is there a difference between a promotion and raise? Most people expect some increase in salary every year or so to at least match the cost of living. 

Final Thoughts

Creating a compensation guide can seem overwhelming and unnecessary at the early stages, and that may be true. As you face these issues, which you absolutely will, take a little extra time to discuss as a leadership team and document them so you can build a compensation guide over time. As with anything related to culture, revisit it regularly and don’t be afraid to update it, but be intentional about the decisions you are making across the team.

As with anything related to culture, how strictly to adhere to your own rules indicates how strong your culture is around these choices.

Interviewing for High Potential

Hiring for a startup (or any team) is about finding people who can grow.

You don’t just need someone who can do the job today, you need someone who can stretch, adapt, take on new responsibilities, and level up as the business scales.

That’s why I often weigh the potential of a candidate above things like experience or pedigree. These are people who may not check every box right now, but they have the mindset, curiosity, and drive to take on more and learn fast.

Here are five of my favorite questions to help identify high-potential talent.

1. What’s a skill you’ve developed that didn’t come naturally to you?

This question uncovers grit and work ethic.

High-potential candidates tend to seek growth proactively and are gritty (I love grit). I’m looking for people who’ve pushed through discomfort, made progress, and can clearly articulate what they learned.

Bonus: ask both “what do you expect to learn in this role?” and “if you have this role what do you expect to teach us?” Their answer tells you how they approach their own growth and contribute to the growth of their team.

2. Tell me about a time you took on something that felt too big for you.

Building something new is full of moments where the scope outpaces the org chart. This question reveals self-awareness, agency, and adaptability.

Look for:

• How they handled the ambiguity

• What they did to get unstuck

• How they reflect on the experience now

The best answers show humility, creative problem-solving, and most importantly: action.

3. Tell me about a piece of critical feedback you received that was hard to hear. What did you do with it?

This tests for coachability, openness to feedback, and the ability to apply it.

High-potential people tend to seek out and integrate feedback. They also know how to handle hard truths and while it can be challenging, they know the value of radical candor. If a candidate struggles with this question or gives a vague answer, it’s a red flag for growth ceiling.

Bonus: ask “did you agree with this feedback?” or “have you ever received critical feedback you disagreed with?” Both of these questions dig deeper into how the candidate takes direction.

4. Tell me about a time you took on a responsibility that no one asked you to do?

This is a way to understand ambition and self-direction. The best hires you can ever make never need to be told what to do. They just constantly make things better around them.

You’re looking for:

• Understanding of broader goals

• Sense of pride in company and team

• Self-driven action

• Alignment with the team

5. Who’s the best manager or mentor you’ve had, and what did they teach you?

This reflects the candidates ability to ask for help, and invest in themselves. Finding and maintaining a strong mentor relationship is real work which reflects investment. Acknowledging the need for help and support shows self-reflection.

The answer I want to hear would cover specific lessons learned, and appreciation for feedback. If the candidate has never had a mentor, ask them why. This can be very revealing about how the individual approaches their growth.

Final Thoughts

Hiring for high potential is about betting on trajectory, not track record. These questions help reveal how a candidate learns, adapts, and pushes themselves beyond what’s expected. 

Look for signs of agency, self-driven growth, resilience under pressure, and intellectual curiosity. That means you’re likely talking to someone who will grow with the company and help the company grow.

High-potential people are unstoppable and if you can foster their growth they will be the best hires you have ever made.

Creating a Culture Where the Best Idea Wins

Every founder wants to build a culture where the best idea wins.

We love to say “great ideas can come from anywhere,” but in practice, most teams struggle to harness those ideas, especially when they challenge internal politics or egos.

To create a culture where the best idea actually can win, no matter where it originates, your team needs four key foundations:

1. Support for risk-taking to generate new ideas

2. A system for productive conflict to challenge those ideas

3. A culture of commitment to execute the ideas

4. A focus on objective results to evaluate the ideas

If you don’t build these foundations, “the best idea wins” is replaced by politics, posturing, and power dynamics that kingmake the ideas that are implemented.

1. Risk-Taking Requires Psychological Safety

Psychological safety is the belief that one will not be punished or humiliated for speaking up with ideas, questions, concerns, or mistakes. There are many good articles written about psychological safety, which I would encourage every leader to read, but the core requirement is a culture of open communication where there is no fear of shame when taking a social or interpersonal risk.

2. Productive Conflict Makes Ideas Better

Productive conflict is the act of challenging new ideas from different perspectives and pressure testing them through methods like steelmanning, Devil's advocacy, principle of charity, Rapoport’s rules, and others.

To have open, productive debates about ideas, your team needs to know that disagreement is not personal. That starts with a culture of respect, where the idea or the work is being judged, not the individual who came up with the idea or the one that did the work.

Respect doesn’t mean avoiding conflict. It means:

• Critiquing the work, not the person

• Assuming positive intent, even in disagreement

• Giving everyone equal opportunity to contribute, regardless of role or seniority

Productive conflict is built on the belief that we’re all here to build something great together. That should be the guiding light for any debate to avoid any semblance of “winning” an argument or scoring points. The goal is to make the idea better.

3. Commitment Moves the Team Forward

I have always been a firm believer in the power of “disagree and commit”. It allows for teams to move forward past the debate stage without anyone feeling like they have lost integrity. It supports psychological safety because team members can be clear that they disagree with the plan but will do everything they can to make it work. 

To commit to a plan even when there is not full agreement shows a level of professionalism and a team-first mindset from each individual. In practice this means every team member must:

• Put maximum effort into the plan even if they disagree with it

• Faithfully follow both the letter of the plan and the intent of the plan

• Do everything possible to set the plan up for success

If a plan that is committed to by the team is executed best to the teams’ ability then the merit of the idea will be judged against the desired results.

4. Objective Results Keep the System Honest

A culture where the best idea wins needs clear metrics for success. Otherwise, outcomes are judged by perception, or politics, not performance.

If a team is focused on having the best idea win it needs to measure the idea against the results. Follow these steps:

• Set clear goals that can be measured

• Transparently deliver the results to the entire team

• Perform retrospectives without blame

• Directly apply the learning

If a bold idea fails (which will happen) but the team learns from it and improves, that’s a win for the system. If an idea succeeds but contradicts prior assumptions, celebrate that new insight.

Results, not seniority, consensus, or comfort, should be the ultimate arbiter of success.

Final Thoughts

The goal isn’t to find one perfect idea. It’s to build a system that consistently improves how your team surfaces, debates, selects, and executes ideas over time. Create space for risk, expect respectful conflict, align the team around execution, and measure what matters. Do it consistently, and you’ll make better decisions, waste less time, and unlock a level of creativity and clarity most teams never reach.

Proletariat Core Values: Week 5 – Be Respectful

This is the final post in my five-part series on the core values from Proletariat Inc., how we wrote them, how we applied them, and how they helped shape our team and culture.

We’ve covered:

• Understand Why – curiosity and transparency

• Decide Fast and Iterate – action and learning

• Take Responsibility – ownership

• Exceed Expectations – ambition and rigor

This week, we finish with a value that anchored all the others: Be Respectful.

The Core Value as Written

Be Respectful
Treat each other, the products, the players, and the company with respect. Empathy, inclusivity, diversity, and trust are critical to creative output. Assume intentions are good and come from a place of caring. Remember that we’re all in this together.

Why It Mattered

Creative work is built on collaboration and trust, and those things fall apart quickly without respect.

Respect doesn’t mean being polite or conflict-free. It means treating people like teammates, assuming positive intent, and holding each other to a high standard without tearing each other down.

In game development, and in startups in general, things move fast, tension is normal, and feedback flows constantly. Conflict is critical to finding the best idea. This value ensured we could have honest and direct conversations, where we aggressively attacked ideas but never attacked people.

What It Encouraged

• Empathy in feedback: Say the hard thing, but say it in a way that helps someone grow.

• Inclusivity in collaboration: Everyone’s ideas are welcome. Diverse perspectives make the work better.

• Care for the product and the players: Respect wasn’t just for teammates. We expected people to care about the work and the audience.

• Appreciation for the company: Individuals and teams felt aligned with the organization and everyone acted like an owner (because they all were).

• Trust on the team: Give people the benefit of the doubt. Assume they care, because they probably do.

How We Applied It

“Be Respectful” wasn’t treated as a soft value. It had practical, everyday implications:

• In art, design, and code reviews: Critique the work, not the person. Focus on impact, not ego. We wanted everyone to show work early but trusted them to take the feedback and apply it. (see my post about feedback structure)

• In meeting discipline: Everyone was given time and space, whether they were junior or senior, and regardless of role.

• In feedback sessions: We encouraged honesty and care. Be direct and critical, but say it from a place of wanting someone to succeed.

• In leadership: We modeled vulnerability, admitted mistakes, and respected the team’s time, focus, and well-being. We took critical feedback head on and showed we would not take it personally.

It also showed up in our community policies, in how we responded to players, and in the choices we made about the kind of studio we wanted to be.

What Made It Work

This value worked because it was woven into everything: hiring, onboarding, communication guidelines, and leadership behavior. This was all in the pursuit of creating an environment where the best idea wins.

“Be Respectful” was not about being nice, it was about building an environment where people felt safe, supported, and that they could do their best work. Often we need critical feedback and challenging coaching to push ourselves to deliver our best work, and that is what we strived for.

Paired with values like Take Responsibility and Exceed Expectations, we hoped to find a balance where the pursuit of excellence would not lead to unsustainable burnout.

Final Thought

“Be Respectful” was never just about avoiding bad behavior. It was about building the kind of team where people feel heard, trusted, and valued, because that’s when they do their best work.

Respect fuels trust. Trust fuels creative conflict. And creative conflict builds great products.

This value was actually not one of the original ones we listed for the team, we previously attempted to spindle the ideas of “Be Respectful” throughout the other four core values. After receiving feedback we decided to call it our as a fifth core value that could stand alone. In retrospect I think it belongs at the foundation of any team trying to do something hard together.

Thanks for following this series. If you’re working on your own company values, check out my guide on how to write them.

Proletariat Core Values: Week 4 – Exceed Expectations

This is week four in my five-part series on the core values from Proletariat Inc., how we wrote them, how we lived them, and how they helped shape a high-performance culture.

So far we’ve covered:

• Understand Why – curiosity and transparency

• Decide Fast and Iterate – action and learning

• Take Responsibility – ownership

This week we’re talking about going beyond just doing the job: Exceed Expectations.

The Core Value as Written

Exceed Expectations
Be innovative, have ambitious goals and work to achieve them on aggressive timelines. Aim high, be scrappy, creative, efficient, and resourceful. Exceed expectations, and push yourself to the best of your ability while taking pride in your work.

Why It Mattered

A startup lives or dies by its ability to outperform expectations, internally and externally.

This value wasn’t about working more hours or grinding unsustainably. It was about showing that you can do more with less, and that every person on the team was capable of creating exceptional outcomes, not just meeting the minimum bar.

High functioning teams are ambitious by their nature. They strive to punch above their weight class. We wanted a culture that encouraged taking ambitious risks.

“Exceed Expectations” helped us signal to ourselves, our players, and our partners that we were serious, not just about building something, but about building something great.

What It Encouraged

• High personal standards – Delivering something “good enough” wasn’t the bar, we demanded excellence.

• Creative problem-solving – We expected teams to work with limited resources and still deliver top-tier results.

• Pride in craftsmanship – From internal docs to production art, people cared about the quality of what they made.

• Ambitious planning – We encouraged people to set bold goals and reach for more than they thought possible.

How We Applied It

“Exceed Expectations” showed up across the company in ways big and small:

• In development: We’d surprise partners with polish and innovation far beyond what was expected from a team our size.

• In communication: When we delivered bad news (which happens), we’d also show the thoughtful work behind the decision and what we were doing about it.

• In support and community: Our team often went out of their way to answer questions, support players, and improve the experience beyond the basics.

We never framed this as starving our team of their needed resources. We framed it as: take pride in your work and reset the bar on what people think is possible.

What Made It Work

“Exceed Expectations” can backfire if it turns into burnout. That’s why we reinforced three key ideas:

• Ambition isn’t exhaustion – We made it clear this value was about smart innovative ambition and being scrappy, not pushing people to overwork.

• Celebrate effort and creativity – We publicly praised creative problem-solving and clever solutions, not just polished results.

• Paired with trust and iteration – This value worked because it sat alongside Take Responsibility and Decide Fast and Iterate. We built safety first, then challenged people to rise to the occasion.

Final Thoughts

“Exceed Expectations” wasn’t just about pushing hard, it was about aiming higher, embracing creativity, and surprising people (including yourself) with what’s possible.

I feel that the most disadvantageous thing you can do to your team and yourself is simply “go through the motions”. The reality is that delivering simply what is expected is underperforming in a competitive market. Setting and exceeding expectations is one of the single most powerful abilities for anyone to accelerate their career and team success.

When every person on a team holds a mindset where they are resourceful, ambitious, and proud of their work, you get something rare: a culture that consistently punches above its weight and does more with less.

Proletariat Core Values: Week 3 – Take Responsibility

This is week three in my five-part series breaking down the core values we used at Proletariat Inc. I wanted to cover not just what they were, but how they were written, why they mattered, and how we used them in our daily work.

So far, we’ve covered Understand Why (curiosity and transparency) and Decide Fast and Iterate (action and learning). This week is about one of the most foundational ideas in any high-performing team: ownership.

The Core Value as Written

Take Responsibility
Own your actions and honor your commitments. Hold yourself to a high standard and be transparent with your team and our players. If and when that’s not possible, take responsibility and ensure your team is aware and able to support you. The way you do anything is the way you do everything.

Why It Mattered

Startups depend on trust, communication and follow-through. When you have a small team and big goals, everyone has to deliver, and if something’s off, it will impact the whole system.

This value was about more than just “doing your job.” It was about building a culture where people took their commitments seriously, owned the outcomes, were honest when things went off track, and knew when to ask for help.

We wanted to create a culture where people were rewarded for taking responsibility, not constantly looking to cover their own ass.

What It Encouraged

• Execution over excuses: If you said you’d do something, you did it, or you let the team know why it changed.

• Transparency over hiding problems: If you were behind, you spoke up early, not after a deadline slipped.

• Do the little things well: Responsibility also means being detail oriented and caring about all the boring things that make for an awesome game, product, team, and company.

How We Applied It

“Take Responsibility” played out across the company in many ways:

• In production and development: If someone couldn’t meet a deadline, the expectation wasn’t silence, it was transparency. We’d adjust as a team

• In player communication: We’d own mistakes publicly. If we shipped a buggy patch or something broke, we’d explain why and how we’d fix it

• In design and product decisions: We would delegate to the individual or team and let them take responsibility for both their work and the outcome of that work

• In leadership: If leadership made the wrong call (and we did), we took ownership, especially in front of the team

This value gave the team permission to speak up early and created a culture of support instead of punishment.

What Made It Work

“Take Responsibility” only works if the team feels safe doing it. We built psychological safety first, so people could be honest about their mistakes. And we modeled responsibility at the leadership level, owning bad decisions, being transparent with the player community and the team, and fixing problems without finger-pointing.

“Take Responsibility” also requires leadership to actually delegate responsibility. We were not perfect at this but we constantly strived to improve our ability to delegate and empower the wider team.

And lastly, it requires that the team supports and trains people on how to take on new responsibilities. At Proletariat we worked to build a culture that invested in this kind of effort to help grow each team member.

Final Thought

The path to advancement in most careers requires taking on more responsibility. However, most companies lack psychological safety, are poor at delegating, and provide no support for the employee stepping into new/more responsibilities.  

You can’t build a great team without accountability, but you also can’t build it with only shame and fear. “Take Responsibility” wasn’t about perfection. It was about honesty, integrity, trust, and owning your part while also being encouraged to ask for help.

(Want help creating your own set of values? Check out my guide on writing core values.)

Proletariat Core Values: Week 2 – Decide Fast and Iterate

Good decisions are hard, but fast decisions are good.

In this 5-part series, I’m walking through the core values we used at Proletariat Inc., what they meant, how we wrote them, and how they shaped our day-to-day work. These weren’t slogans. They were tools for making decisions and building a culture that could scale with trust and speed.

Last week I wrote about Understand Why, our value around curiosity, transparency, and trust. This week is all about velocity, action and learning.

The Core Value as Written

Decide Fast and Iterate
Good decisions are hard, but fast decisions are good. Quickly agree and commit to a well-reasoned direction, even without consensus. The tradeoff is worth it. Act, gather feedback, measure against expectations, and adjust accordingly. It’s okay to be wrong, work to learn from it quickly. Nothing’s sacred and we should always question the status quo.

Why It Mattered

Teams suffer from indecision and inertia far more often than from bad choices. The longer you spend discussing a decision around a white board the more time you waste speculating when you could be testing. 

This value was about embracing action, reducing fear of failure, and creating a culture where we’d rather ship something rough and learn than wait for something to be perfect.

It also reflected a reality about building complex products like games: the sooner you start iterating, the sooner you start solving real problems.

What It Encouraged

• Decisiveness over consensus – Consensus is ideal but not required, it’s better to disagree and commit fully than wait for a compromise

• Action over perfection – Waiting for 100% clarity usually meant we were already behind

• Data over assumptions – Every assumption will be tested eventually, might as well start as early as possible

This wasn’t a license to be reckless. It was a call to take smart, intentional action, and then be humble enough to adapt quickly and go again.

How We Applied It

“Decide Fast and Iterate” showed up in our product development, leadership meetings, and team dynamics:

• In game and product design, we prototyped quickly and often. We'd test something internally or with players, kill what didn’t work, and build on what did

• If a candidate had promise, we moved fast to get them hired and provided a strong onboarding plan

• Leaders had clear ownership to make quick calls, rather than waiting for universal agreement

• In production process or company policy decisions we were willing embrace a change quickly, while measuring the impact 

It also gave permission to make mistakes, as long as we learned from them and improved.

What Made It Work

We didn’t just say “move fast and break things.” Making quick decisions was paired with:

• Psychological safety – People and teams weren’t punished for early mistakes if they iterated quickly

• Short feedback loops – Reviews, retros, and playtests were built into our process

• Visible support from leadership – Leadership made imperfect decisions in public, adjusted when needed, and talked openly about what we were learning

Final Thought

“Decide Fast and Iterate” helped us bias to action. Whenever you are building something new it is almost impossible to get it right on the first try. We wanted to spend the smallest amount of time possible to consider a plan for action and then build iteration time into the process.

When paired with “Understand Why,” it created a powerful combo: transparent decisions used to drive rapid iteration towards the best idea.

This allowed us to adopt a culture of being metrics informed not metrics driven. The ability to build quickly, gather qualitative and quantitative feedback, and iterate, is very powerful. However, applying the feedback to properly choose a direction is always a judgement call. 

(And if you missed it, check out my post on how to write core values for tips on building your own)

Proletariat Core Values: Week 1 – Understand Why

Many companies never share their core values publicly and for those that do, it can be hard to understand how these values came about and how they are used in daily work.

Over the next five weeks, I’m sharing the five core values we used at Proletariat Inc., not just what they were, but why we chose them, how we wrote them, and how they actually impacted our work.

This week: Understand Why.

The Core Value as Written

Understand Why
Know why your work is important to your team, your project, and the company. Be passionately curious, act with intention, and don’t be afraid to ask questions. It’s your responsibility to understand the reasons behind a decision, and it is the decision maker’s job to be transparent.

Why It Mattered

Understanding why a decision was made is fundamental to doing great work. Most teams and individuals can explain what to do. Good teams get alignment on how and when to do something. But great teams push to understand why, because that’s where autonomy, creativity, and real ownership live.

When someone knows the why behind a task, they can make smarter decisions, raise flags earlier, and often suggest better ways to reach the goal. If you know why someone else on your team is doing something it makes you a better teammate because you can more easily align with their goals and all row in the same direction.

Making the leap to understanding why decisions are made a certain way or work is done a certain way is the fastest track to growing in your role and career. If you want more responsibility you need to have a broader understanding of the business and the team. That higher level perspective is required for strong leadership.

What It Encouraged

This value was built around two core ideas:

• Transparency is required

• Curiosity is everyone’s responsibility

We didn’t want to just say “be transparent” because that puts the burden solely on leadership. Instead, we wanted to instill a mindset of responsibility in every team member: if you don’t understand something, ask. If a decision doesn’t make sense to you, dig in.

The inverse was also true: if you were making decisions, it was your job to explain them. That created a culture of decision transparency, which is incredibly important especially when the decisions are difficult or controversial. That transparency allows trust to flourish up and down the organization.

How We Applied It

“Understand Why” showed up in all kinds of ways:

• In meetings, people would frequently ask: “why are we doing this instead of that?”

• In 1-on-1s, we encouraged teammates to challenge process and strategy by starting from first principles

• In hiring, we looked for people who were curious and wanted to get a view of the bigger picture

• In our weekly full team meeting leadership would answer any question and invest time to ensure the team was fully informed

• In design and development reviews, we prioritized intent: “What was the outcome you wanted to achieve here, and why?”

• When a difficult decision needed to be made leadership would outline not just what the choice was made but the reasons why that was the right choice given the context

It also helped us avoid making the easy but not best decisions or “because I said so” direction. If a lead couldn't explain why something was being prioritized, it was clear the decision needed to be revisited.

What Made It Work

We wrote this value with purpose:

• Action-oriented language ("know," "be," "act," "ask")

• Balanced accountability between decision-makers and team members

• Broad applicability across roles, levels, and disciplines
  
  

It wasn’t about pretending everyone could or should agree all the time, and that is highlighted more in a future value. it was about creating clarity, trust, and shared context, even when we moved fast. 

Final Thought

The more time I have spent away from running Proletariat the more clear it is to me how important transparency and understanding why is to a high functioning organization. Investing the time to ensure that everyone is fully educated and aware of any aspect of the business they feel is important or relevant to them is always worth it. Encouraging high potential team members to learn more about why decisions were made trains them to become key decisions-makers in the future.

(Want more information on how to create your company’s values? Check out my post on writing core values.)

How to Write Your Company’s Core Values

For core values to work your team needs to read them and say "that's me".

Core values should be clear, detailed, actionable, and something that the whole team feels they were involved in.

Whether you’re starting from zero or revisiting your existing values, it can feel like a branding exercise or a philosophical debate. It shouldn’t be. Core values are an operating tool, not marketing copy. The goal isn’t to sound impressive or boastful, it’s to define what behaviors and beliefs will shape how your team works every day.

Here’s how to find and write good core values while involving the entire team in the process.

1. Look at What’s Already Working

Your values are probably already showing up in how you hire, how you communicate. how you solve problems, and what kind of behavior gets rewarded.

Ask your leaders and team:

• Who are our top performers? What makes them great?

• Who are our best teammates? Why do we love working with them?

• What kinds of decisions do we consistently feel are right?

• What are we unwilling to do, even if it helps us hit our goals?

This helps you extract real examples of behaviors instead of fluff or buzzwords.

2. Choose What to Keep, Amplify, or Change

Startups evolve fast. Some early values will no longer fit or you might need to introduce new ones to support where you’re headed.

Use this moment to decide:

• What values do we want to scale as we grow?

• What do we need to unlearn or move away from?

• What kind of team do we want to become?

• What do prospective hires, partners, or investors expect from us?

Values are directional and aspirational. You’re defining the kind of company you want to be, not just describing where you are today.

3. Write Clear, Simple, Actionable Statements

Your values should pass three tests:

1. Anyone on the team can understand them, use them, and remember them

2. They guide daily decisions

3. You’d be willing to fire someone who consistently breaks them

Write values that sound like how you actually talk. You want these statements to be something you could imagine hearing in a meeting or being typed in a slack message.

I will expand upon each value in future posts but these were the core values of Proletariat before we were acquired by Blizzard Entertainment.

• “Understand Why”

• “Decide Fast and Iterate”

• “Take Responsibility”

• “Exceed Expectations”

• “Be Respectful”

4. Follow Each Statement With a Detailed Paragraph

A core value statement is important because it is easy to remember and use in conversation. However, it is often not enough to fully articulate the specifics on how and when to use the value. A well-written paragraph should provide the additional details that make it easier to embody the value and cover any nuances that simply don’t fit into a single statement.

Here is an example from Proletariat’s core values:

Decide Fast and Iterate

Good decisions are hard, but fast decisions are good. Quickly agree and commit to a well-reasoned direction, even without consensus. The tradeoff is worth it. Act, gather feedback, measure against expectations, and adjust accordingly. It’s okay to be wrong, work to learn from it quickly. Nothing’s sacred and we should always question the status quo.

5. Iterate with the Team

Share a draft with your team. Give everyone a chance to read, digest, and comment on how the values make them feel. 

Ask the following:

• Do you identify with these values?

• Is there a value or behavior missing?

• Are any of these values confusing or ambiguous?

You’re not looking for consensus, but you want buy-in and belief. The entire team should feel enrolled in the process and that their voice is being heard, even if you do not make the changes they want. If your team feels the values are fake or forced upon them, they won’t stick. 

6. Evaluate Regularly

At Proletariat we would review our values once a year but also after any major event like a major launch, funding round, or other strategic shift.

I would send out a survey to the leadership team to have them fill out ahead of the discussion. These are the questions I would ask:

1. Do we embody [this core value] as a leadership team? (Consistently/Sometimes/Almost Never)

2. Do we embody [this core value] across the entire team? (Consistently/Sometimes/Almost Never)

3. Should we keep [this core value]? (Yes/No)

This was a good way to frame the discussion and we would use it to start back at the beginning of this process.

Final Thoughts

Writing your company’s core values isn’t about crafting the perfect words, it’s about building a shared understanding of what matters most. Your first draft won’t be perfect, and that is intended. Crafting shared core values is a process that requires investment and time.

As your company evolves, your values will evolve too. That’s not a problem, it’s a sign that your culture is changing which is required to grow. Revisit your core values regularly. Use them. Talk about them often. Make them part of how you hire, lead, work, communicate and make decisions.

Why Every Company Needs Core Values

Every company has core values, whether they’re written down or not.

It’s easy to think of core values as a “nice to have.” Something you’ll define after you ship the product, close the seed round, or grow beyond ten people. But the truth is, your culture is already forming. And if you don’t take the time to define your values intentionally, they’ll grow wild on their own.

Over the next several weeks I am going to share several posts about core values with examples and practical ways to use them every day.

See my original post on culture for more insights.

What are Core Values?

The definition of core values is a defined system of beliefs that helps people tell the difference between right from wrong. In a company setting they’re the root beliefs and shared behaviors that guide how your team works together and makes decisions.

Good core values are:

• Actionable – they influence daily decisions

• Specific – they’re clear enough that anyone on the team knows how to apply them

• Meaningful – they reflect who you are and who you’re trying to become

Why Companies Need Core Values

Here are six reasons why defining and using core values will help your company grow more effectively, and create a culture that you will be proud of.

1. Guide Decision-Making

Startups move fast. You can’t write a policy for every situation. Core values give your team the clarity to make the right call even without you in the room.

If you value “decide fast and iterate,” that becomes a principle your team can use in moments of uncertainty. Good values turn gray areas into clear decisions.

2. Shape Company Identity

Your values are a major part of your brand and voice, whether you realize it or not. Defining them helps you attract people who believe what you believe, from employees to customers to partners.

We live in a time when people care about what the companies they work for (and buy from) stand for. Core values make that clear.

3. Help You Manage Performance

A shared set of values gives you a consistent way to coach, develop, and hold people accountable.

Use values to:

• Set expectations from day one

• Provide feedback rooted in what the company stands for

• Identify when someone is misaligned, even if they’re otherwise performing well

• Incentivize and reward the right things

4. Preserve Culture as You Scale

As you grow, it becomes critical to maintain the team culture. Every new employee will bring their own biases and history with them. Having an established set of core values that the team believes in and lives every day creates guardrails during growth.

Core values help you:

• Onboard new hires faster

• Avoid culture drift

• Maintain consistency across distributed teams

5. They Build Trust Across the Team

When values are clearly defined and consistently applied, they create predictability and trust.

Your team knows:

• How decisions are made

• What behavior gets rewarded

• How conflict is handled

6. Keep Leaders Accountable

As a leader, you set the tone. Your values hold you to it. Leaders need to lead by example and exemplify the core values of the team as often as possible.

When you're stressed, tired, or tempted to cut corners, values act as a personal compass. They also give your team permission to hold you accountable if you start to stray.

Leaders who live their values build real credibility and lasting cultures.

Final Thoughts

You don’t get to choose whether or not your company has values. You do get to choose what those core values are. If you create unique, authentic values that resonate with the team they will become invaluable to sculpting the culture that you want to create. Embrace the idea that culture matters, is worth investing in, and worth talking about. 

How to Choose the Right Investors

Choosing the right investors can make or break your company.

When you’re fundraising, it’s tempting to take the first signable offer you get. In a tough funding environment, just getting any deal can feel like a miracle.

But choosing the right investor is about much more than just the capital. Investors become long-term partners, and their involvement will shape the future of your company in ways you may not expect. Taking money from the wrong partner at the wrong firm can kill your company.

Here’s how to evaluate investors beyond the dollar amount and find the right fit for your company.

1. Determine Your Ideal Partners

It’s crucial to know what kind of investors you’re looking for before you start seriously negotiating. Not all investors are equal, and not all will add value beyond just cash.

Questions to consider:

• Do you want an investor who has operational experience as an entrepreneur?

• Would it help to have an investor who’s an expert in a specific industry or region?

• Are you looking for someone with a deep network of other investors, potential customers, or prospective employees?

• Would you prefer a partner who actively mentors the founding team, or someone more hands-off?

Also consider the firm’s brand and operating resources. Some firms have entire teams dedicated to helping portfolio companies with hiring, strategy, or product development. The firm’s reputation alone can also be a powerful signal to future investors and potential partners.

2. Evaluate Each Partner Individually

The first thing to realize is that not all money is equal. The most valuable investors bring much more than capital: they bring expertise, connections, strategic support, mentorship, and more.

Questions to consider:

• What value does this investor bring beyond capital?

• Have they invested in similar companies before?

• Do they have a strong network in your industry?

• Are they known for helping with hiring, strategy, or partnerships?

• If they were not investing in the company, would you want to work with them?

Do Your Own Reference Checks

It’s entirely reasonable, and recommended, to ask a VC for references. But don’t stop there. Reach out to founders from their previous investments, especially those that didn’t succeed. Understanding how they handle failed investments can tell you a lot about their character and support style.

3. Evaluate Each Firm as a Whole

An investment partner is part of a larger firm, and the firm’s brand and resources also matter. Sometimes, the operating team or the firm’s network can provide more value than the partner themselves.

Questions to consider:

• Who else at the firm will be involved with your company?

• Does the firm’s brand and reputation align with your company vision and stage?

• How will this firm’s involvement signal your momentum to future investors or partners?

• What additional resources (hiring support, industry connections, marketing help) do they offer?

Be cautious if the firm’s values or focus areas don’t align with your own. Taking money from a high-profile firm might look good on paper, but it can backfire if they expect you to shift strategy to fit their portfolio.

4. Balance the People Around the Table

Your goal is to build a strong, diverse support network around your company. Each investor brings unique strengths and perspectives, but it’s essential to balance those voices to avoid redundancy.

Questions to consider:

• Are you getting a variety of perspectives and not just more of the same?

• Does your investor group have a diverse set of experiences?

• Is there overlap in their networks, or are they connected to different circles that expand your reach?

• Do the various firms and investors complement each other in terms of expertise and connections?

Consider how adding a new investor affects group dynamics. You don’t want a single loud voice drowning out more nuanced, thoughtful input from other investors.

5. Be Mindful of the Long-Term Relationship

Investors are not just writing you a check, they’re becoming long-term partners. You’ll be working with them through good times and bad, so it’s essential to choose people you can trust and communicate with openly.

Questions to consider:

• Are they transparent and direct in communication?

• Do they provide constructive feedback without micromanaging?

• Do they have a history of supporting their founders through challenges?

If an investor shows signs of being controlling or overly critical during the pitch process, that behavior is likely to escalate after they invest. You need to judge for yourself if they are in it for the long haul.

Final Thoughts

Raising money can feel like a sprint, but it’s better to take the time to choose the right partners than to jump at the first offer. The wrong investor relationship can cost you far more than delaying a funding round.

Great investors do more than just write checks, they champion your vision, offer guidance, actively help you grow, and know when to stay out of your way. Be strategic, do your diligence, and choose partners for the long haul over whoever gives you the best offer on paper.

How to Manage a Competitive Fundraising Process

You did everything right, and now you have multiple term sheets. So how do you get the best deal with the right partner without damaging relationships or derailing the process?

Having a competitive fundraising round is a great position to be in, but it still comes with challenges. I’ve seen founders navigate this successfully, but I’ve also seen situations where:

• A founder burns relationships by mishandling negotiations

• A deal falls apart because the process drags on too long

• The founder gets focused on valuation, and chooses the wrong partner

Here’s how to manage the process strategically, efficiently, and professionally to maximize outcomes for your company.

Define What You Want

You’re in the driver’s seat, but where do you want to go? Before you engage further, sit down with your co-founders, current investors, and key stakeholders to align on these three scenarios:

Minimum Offer (The Deal You’ll Take if Needed)

• A good deal, but not a great deal

• The terms are fair, and you won’t regret it a year from now

• This becomes your baseline leverage

Ideal Offer (The Deal You’re Targeting)

• A great deal that excites you

• You’ll still feel good about it in a year

• This is the outcome you’ll push towards in negotiations

Walkoff Offer (The Deal That Ends the Process Immediately)

• An amazing (borderline unreasonable) deal with your preferred partner(s) 

• The offer is so compelling that you’d take it on the spot

• Not the absolute max you could negotiate, but a shortcut to an incredible outcome

Not every investor should have an “ideal” or “walkoff” scenario. If a firm can’t even meet your minimum, cut them out quickly.

Secure a BATNA 

Now that you know your minimum offer, go secure it. Work with interested investors to lock in at least one term sheet at or above your minimum.

This becomes your BATNA (Best Alternative to a Negotiated Agreement), a powerful form of leverage. You now have a limited window to negotiate towards your ideal or walkoff offer before momentum fades. Remember that time kills all deals so move quickly.

Thin the Herd 

With your BATNA in hand, start circling back with interested investors and push for better terms. As offers improve:

• Raise your minimum offer: new term sheets should be better than your last BATNA

• Pass on weaker offers quickly: don’t string investors along

• Keep the process moving: don’t let the process drag

Your goal is to get each investor’s best and final offer as quickly as possible while keeping the process professional.

The Walkoff

If you have strong interest, you can test the waters for a walkoff offer. Follow these steps:

1. Approach your top choice for partner first and say: "If you can offer X, we will immediately sign and move forward with you."

2. If they say no, get their best counteroffer, then approach the next firm on your list

3. If they say yes, you’re done

Why limit this to one investor at a time?

The whole point of a walkoff offer is that you’re signaling exclusivity. If you use it on multiple firms at once, you risk damaging trust with all of them. This is the same as taking a pre-emptive offer before even starting a fundraise process.

Investors Are People Too

A competitive process should not feel transactional. Investors don’t want to feel like just another bid, they want to feel like you chose them for reasons beyond just numbers. Some key tips to avoid burning bridges:

• Take a personal approach to each partner and build the relationship

• Don’t just negotiate on valuation, talk about long-term partnership fit

• If you know you won’t accept an offer, be transparent and exit quickly

• If you decide to pass on an investor, thank them and keep the door open

Be Honest

The quickest way to destroy a deal is to lie, bluff, or over-embellish. If an investor catches you misleading them, it can derail your entire process.

• Communicate clearly, frequently, and professionally

• Keep your word, don’t play investors against each other unfairly

• Don’t share confidential details about other offers. It is unethical and it will backfire

Your reputation follows you. A poorly managed process will hurt you beyond this round!

Final Thoughts

A competitive fundraising process is an incredible position to be in. But success isn’t just about getting the highest valuation, it is about getting the right deal with the right partner so you can get back to building. The investor community is small, and your reputation matters. While it might feel like you are negotiating against all these other partners you eventually want to be excited about working together. If you can navigate all this well, you will get great terms and find partners that you will enjoy working with for many years to come.

The Buddy System for Onboarding

Every new employee should have a buddy to help them onboard.

Onboarding is one of the most critical factors in a new employee’s long-term success. While many companies provide a set of documents and manager check-ins, one of the most effective and overlooked onboarding tools is assigning every new hire a buddy: a peer who can help them navigate their first few months.

Read more in this Harvard Business Review study with Microsoft.

How to Make the Buddy System Work

A successful buddy system isn’t just about randomly pairing employees, it requires intentional planning.

1. Make onboarding a shared responsibility - Both the buddy and the new hire should actively engage.

2. Ensure the buddy has time - Assigning this role to an overloaded employee will make it ineffective.

3. Set expectations on both sides - Clarify how the buddy should support the new hire and how the new hire should engage.

The Value for the New Employee

A well-structured buddy program helps new hires adjust quickly, feel supported, and become productive faster.

1. A Judgment-Free Zone for Questions - From “Where’s the bathroom?” to “How do I submit an expense report?”, a buddy provides a safe space for asking questions without the fear of seeming unprepared.

2. Hands-On Learning and Support - Most onboarding guides can’t replace real-time help. A buddy can offer support, helping the new employee learn processes, tools, and team expectations in a direct way.

3. Peer-Level Feedback - Managers should provide feedback, but peers offer an additional layer of guidance. A buddy can give constructive feedback on how the new hire is adapting without the formality of a performance review.

4. Cultural Integration - Beyond official communication guidelines, every team has unwritten rules about how work gets done. 

The Value for the Buddy

Being an onboarding buddy isn’t just about helping the new hire, it’s also a growth opportunity for the current employee.

1. Building Mentorship Skills - Mentoring others is key to career development, whether someone wants to move into leadership or simply become a stronger teammate.

2. The Protégé Effect - Explaining company processes to someone else reinforces the buddy’s own understanding. They may even uncover areas where the team could improve.

3. Gaining a Fresh Perspective - New employees bring new ideas and outside perspectives. Buddies get a unique opportunity to challenge old assumptions and rethink how things are done.

Final Thoughts

Companies spend considerable time and resources hiring the right people. Hiring is barely half the battle, the real challenge is helping new employees integrate, contribute, and succeed quickly. A great metric to focus on is time-to-productivity, along with the satisfaction of both the new employee and the team. A buddy system helps new hires apply their skills within the company’s unique context while ensuring they feel supported and engaged from day one. 

Making the Most of Events

If you're going to spend time and money attending an event, make it count for your team.

Events and conferences cost your team significant time and money. If you're investing in attending, it’s critical that you maximize the value not just for you but for your company and team. That means integrating the event into the strategic conversation, having goals, following up, and using the event as a catalyst for future leadership discussions.

Here’s a practical framework I have used to ensure that every event I attend drives real value for the company.

Set Clear Goals

Before you go, answer this question: "What will make attending this event worth the investment of time and money?"
Choose 2–3 focused goals, such as:

• Pitching a new project or fundraising round

• Gaining key insights and contextual intelligence about industry trends

• Building relationships with important partners

Include your leadership team in this discussion and throughout your planning. 

Prioritize Strategically

Events are chaotic and filled with endless meetings, talks, and social gatherings. Prioritize your time to maximize your productivity.

• Make a ranked list of key meetings and events

• Schedule high-value meetings first; then fill remaining time with lower priority ones

• Leave some flexible time slots for spontaneous opportunities or last-minute changes

It is obviously important to catch up with industry friends and colleagues but weigh that against your overall goals. For a meeting to be effective ensure you have a clear ask, even if that is just to catch up and hear how someone is doing.

Plan Early

Scheduling takes work and throwing together whatever meetings you can get last minute is a sure way to underutilize your time. Reach out to potential partners up to a month in advance. The worst that can happen is they will circle back when the event is closer to confirm a time. 

For those of you heading to GDC next month, you should have started last week!

Capture and Organize Your Meetings

Events are overwhelming. Don’t trust your memory. Take quick notes during meetings (follow-ups, key points, next steps). If you have multiple people on your team in a meeting, assign someone to take notes. The next morning, dedicate time (30-45 mins) to write a detailed summary of each meeting. Doing it the next day ensures it’s still fresh in your mind and you can capture anything from happy hours, dinners, or parties where you certainly did not take any notes.

Always Follow Up

Within a few days after the event send personalized follow-up messages. Even if no explicit action items came from your meeting, sending a nice note keeps the conversation going and ensures you capture their contact info.

Share and Take Action

Schedule a debrief meeting with your team after returning and review your notes and insights from the event. The whole reason you attended is to bring back leads, connections, and information that can help your leadership team make better decisions. 

Final Thoughts

Events can easily become distractions if you’re not intentional. A successful event should clearly influence your team’s strategy, partnerships, or growth in the following weeks. Invest time up front to plan and prioritize, and leave time after the event to debrief and take action.

The 90-Day Onboarding Plan: Setting New Employees Up for Success

Onboarding is one of the most overlooked yet critical processes for ensuring a new employee’s success. 

At Proletariat, as we scaled rapidly, we knew that hiring fast also meant evaluating and adjusting quickly. That’s why we implemented structured 90-day onboarding plans, delivered on day one (or even before) alongside our Cultural Communication Guide. This ensured every new hire had a clear roadmap for success.

Check out this template for a 30-60-90 day onboarding plan.

The Goal of a 90-Day Onboarding Plan

By the end of the onboarding period, one of three things should be clear:

1. The employee is successful in their role and fully ramped up

2. The role has been adjusted to better fit their skills or the team’s needs

3. The employee moves on if the fit isn’t right

An onboarding plan removes ambiguity, making these outcomes clear and preventing drift where an underperforming hire lingers without direction or resolution.

Key Objectives of a 90-Day Onboarding Plan

1. Craft Personalized Goals That Align with the Team Strategy

Every role is unique, and job descriptions often don’t capture the full nuance of what success looks like. A great onboarding plan ensures:

• The new hire’s goals fit within the team’s broader strategy

• The plan adapts to the individual’s strengths while addressing growth areas

• The employee understands how they create value early on

2. Prioritize Tasks to Build Early Wins

New employees often feel like they’re “drinking from a firehose” in their first few months. Instead of overwhelming them, sequence tasks in a way that builds momentum:

• Start with achievable wins: Give them clear, valuable contributions early on

• Gradually increase complexity: Move from simple tasks to strategic ones

• Provide structured learning: Direct them to the right resources and people

The goal is to avoid burnout and build confidence through early impact.

3. Set Clear Expectations for Progress

Success should never be vague. By clearly defining what progress should look like at key milestones, both the manager and the new hire can track growth and course-correct early if needed. Here is a general outline for the various onboarding phases:

• First 30 days: Learning - focus on absorbing information and initial tasks

• Days 31–60: Integration - deeper collaboration and ownership of responsibilities

• Days 61–90: Autonomy - fully contributing and delivering measurable results

How to Use an Onboarding Plan Effectively

1. Build the Plan Together

The onboarding plan should be a collaborative effort between:

• The new hire (so they understand expectations and contribute to goal-setting)

• The hiring manager (to ensure alignment with team objectives)

• Other stakeholders (who will work closely with the new hire)

2. Treat It as a Living Document

A static onboarding plan is too formulaic to be useful. The plan should evolve based on feedback and real-world performance. Follow these steps:

• Regularly review and adjust the plan

• Use check-in meetings at 30, 60, and 90 days to assess progress

• Be flexible! If the plan needs adjusting, don’t force a rigid structure

3. Involve the Broader Team

Successful onboarding is not just about ramping up a new hire—it’s about integrating them into the team and broader company culture. Provide cross-team introductions and broadcast early wins and progress to give the new employee positive visibility.

Final Thoughts

The specific structure of an onboarding plan matters less than having one at all. Without a plan, new hires drift, progress is unclear, and retention suffers. The best onboarding experiences give new employees clarity on their role and expectations, provide a roadmap to early wins, and ultimately lead to success within 90 days.

What Do Investors Need to Believe?

A strong pitch isn’t about eliminating all risk, it’s about getting investors to irrationally believe your contrarian idea.

Every early-stage investment is, at its core, irrational. Investors know most startups fail. If funding were purely a rational decision, no one would invest at all. So trying to de-risk every part of your pitch to make it seem perfectly rational is a losing game. The real challenge is choosing the right irrational belief and making investors buy into it.

Define Your Irrational Belief

The best startups succeed not because they eliminate risk, but because they bet on something contrarian that turns out to be right.

Ask yourself:

• Are you building an unorthodox product? (a new category that no one believes in yet?)

• Are you targeting a counterintuitive audience? (a niche that traditional wisdom says won’t work?)

• Are you building the company differently? (breaking conventional startup rules in your approach to hiring, go-to-market, or funding?)

• Are you cultivating a non-traditional team? (a team that lacks direct industry experience but brings something else?)

If you can’t identify at least one contrarian angle, you may not be differentiated enough to stand out in a crowded, mature market.

Own the Doubts and Overcome Them

Most founders try to avoid or downplay the skepticism around their boldest claim. That’s a mistake.

If investors are going to doubt something anyway, address it head-on. Show them you already know the challenge and have a plan.

• Instead of hoping no one questions your lack of industry experience, explain why it’s an advantage.

• Instead of ignoring concerns about a new market, prove why the timing is right.

• Instead of brushing off skepticism about a radical approach, demonstrate how it is the only path forward.

De-risk Everything Else

Being contrarian on every axis is a recipe for failure. Even the boldest investors need to see a foundation of credibility beneath the big bet. Many of my earlier post on pitching focus specifically on building credibility, but here are a few ideas to consider:

• If your market bet is risky, your team should be experienced.

• If your business model is unconventional, your go-to-market strategy should be solid.

• If your product is groundbreaking, your execution should be airtight.

• If your budget is very low/high, your development plan should be unassailable.

Make it clear that while you’re taking one big bet, you’re removing risk everywhere else. By acknowledging the risky part you are able to credibly say “we know this is risky, which is why we have reinforced these other areas.” The contrast makes it easier for investors to say yes.

Final Thoughts

Don’t shy away from simply wrapping up a pitch by confidently saying “in order to invest, you need to believe X.” It is the contrast of the contrarian idea backed up by all the other de-risked strengths that stack the deck in your favor.

When Pitching, Be Like Gandalf

Pitching investors can feel like an epic journey—full of challenges, uncertainty, and the need to inspire belief in something bigger than yourself. So why not take a page from one of the greatest mentors of all time?

As we enter a heavy season of pitching, here are some lessons I’ve learned—through both experience and a little wisdom from The Lord of the Rings.

1. Be Confident in Your Plan

"A wizard is never late. Nor is he early. He arrives precisely when he means to."

Investors don’t always know the right answer, but they do want to believe that you do. Confidence isn’t about arrogance, it’s about conviction. When Gandalf reassures Frodo that wizards are never late, he’s not just making an excuse. He’s projecting certainty, even in the face of doubt.

When pitching, you must approach every question with that same level of confidence. Investors are skeptics by nature, and they can sense hesitation. If your plan feels weak, under-researched, or uncertain, they will pick it apart. But remember: you are likely more of an expert in your target market than they are. Own that expertise.

2. Give an Air of Inevitability

"Things are in motion that cannot be undone."

Investors want to invest in unstoppable founders. They know that backing a startup means committing for years. They need to believe that, whether they invest or not, this company is going to succeed—and they’d be foolish to miss out.

A great pitch doesn’t just highlight potential; it makes investors feel like they are witnessing momentum. They should walk away thinking:
"This is happening. The only question is whether I get on board now or regret it later."

Be unstoppable.

3. Listen and Be Coachable

"Faramir, tell me everything."

While investors may not be experts in your exact business, they see everything. They spot patterns across multiple industries, companies, and market cycles. Many of them got into investing because they love working with founders and want to help.

But here’s the key: being coachable does not mean being a pushover.

Great founders listen actively and ask smart questions. They extract value from investors’ insights but don’t blindly follow every piece of advice. The best investors want you to challenge ideas, push back when needed, and show your own reasoning.

4. Investors Invest in Lines, Not Dots

"I am Gandalf the White."

Your pitch is not a single, isolated moment—it’s part of an evolving narrative. Investors rarely write checks after just one meeting. Instead, they track founders over weeks, months, or even years, looking for signs of progress.

Just as Gandalf transforms over time, your company’s story should evolve with each investor touchpoint.

Final Thoughts

A pitch isn’t just a transaction; it’s the beginning of a long-term relationship. Investors invest in people and stories, not just slides and metrics.

Too many founders get distracted by making the “perfect” deck when what truly matters is building belief in yourself, your vision, and your team.

So next time you pitch, channel your inner Gandalf.