A lot of founders treat fundraising like this:

Build a pitch deck.
Make it look great.
Send it to investors.
Hope someone bites.

But the deck is only one piece of the process.

Before you start raising, you also need to figure out:

What story are you actually telling?

What proof and traction will investors expect at your stage?

Which investors should you be talking to in the first place?

What materials do you need beyond the deck?

How are you building and managing an investor pipeline?

What questions are investors going to ask before they ever consider writing a check?

And how do you move all of those conversations forward without letting the process drag on forever?

A good fundraising process is much closer to running a disciplined sales funnel than sending out a bunch of pitch decks.

You need the right targets, the right story, the right proof, the right sequencing, and enough momentum to get from the first investor meeting to an actual term sheet.

On August 26, I'm running a live workshop called “Fundraising Is Much More Than a Pitch Deck.”

We'll break down the full startup fundraising process from the first meeting through the term sheet, including the investor funnel, positioning, materials, traction, and the questions founders need to be prepared to answer.

No cost to join.

Registration: https://luma.com/dao7ieny

For founders who have already raised: what part of fundraising ended up being much harder than you expected before you started?

Short board meetings. Fewer questions. Longer closed-door sessions.

That combination can make any founder start wondering what’s actually being said once management leaves the room.

But guessing usually makes it worse.

If the closed-door portion of your board meetings is starting to become longer than the actual discussion with management, it may be worth addressing directly.

Find the board member you trust most and ask them:

“Do you still trust me to run this company? Yes or no? And if no, what do I have to do to earn your trust back?”

It’s an uncomfortable question, but it’s a lot more useful than sitting around trying to interpret signals.

Founders: would you ask your board this directly?

A founder recently asked me about something I see constantly in early stage startups.

He was approaching $1M in revenue with about 20 customers, all of whom he had personally sold.

Then he tried hiring a Head of Sales.

It didn't work.

So he hired another highly qualified sales leader.

That didn't work either.

His question was basically:

What am I doing wrong?

The first Head of Sales at an early stage startup might be one of the highest mortality roles in the company.

And I don't think the explanation is usually as simple as "bad hire."

There are three failure modes I see repeatedly.

1. The founder never documented how they actually sell

To get those first 20 customers, the founder probably had hundreds or thousands of repetitions.

They learned the sales motion:

Qualification
Discovery
Demo
Pilot
Proposal
Close

But knowing the stages isn't enough.

The founder also learned the words.

The exact language that makes a prospect understand the product.

The way they describe the problem.

The way they explain the impact.

The response that works when someone says:

"This seems too expensive."

"We already use another solution."

"Why should we trust a startup?"

"Our legal team won't approve this."

"We don't have budget."

That knowledge often exists entirely inside the founder's head.

Then they hire a Head of Sales and essentially say:

"Okay, go sell."

The new sales leader isn't inheriting a playbook.

They're being asked to rediscover one.

2. They hired a great sales leader for the wrong stage

"Head of Sales" can describe very different jobs.

One person is great at taking something messy and building the first repeatable sales process.

Another is great at taking an existing playbook and building a team around it.

Another might be great at managing 100 salespeople across territories, managers, forecasting, compensation plans, and quotas.

Those are not necessarily the same person.

A VP of Sales who crushed it at a company doing $50M in ARR may be completely wrong for a startup that still needs to figure out how customer #21 gets sold.

3. Your 20 customers may not actually represent one repeatable market

This is the question I think founders sometimes overlook.

You have 20 customers.

Great.

How many of them look the same?

Same industry?

Same company size?

Same buyer?

Same pain point?

Same reason for purchasing?

Same sales cycle?

If every customer bought for a different reason, your new Head of Sales may not have a sales machine to scale yet.

They have 20 anecdotes.

Founder led sales can hide this because founders are unusually good at improvising.

They can change the pitch in real time.

They can sell vision.

They can answer product questions nobody else can answer.

They can make promises and decisions immediately.

A hired sales leader can't necessarily reproduce that.

So before saying:

"I need to hire a Head of Sales."

I think the better questions are:

Have we documented the actual sales playbook?

Do we know the exact messaging and objection handling that works?

Do we have a clear ICP?

Are our customers similar enough that the motion is repeatable?

And are we hiring someone who has actually built at our stage before?

For founders who have made the transition from founder led sales to a real sales team: what finally made your first sales leadership hire work?

A founder I work with came into our weekly call frustrated with how slowly his team was moving.

Half joking, half serious, he basically asked:

“Who do I need to yell at?”

I understood the frustration. When you’re the founder or CEO, you can see the runway, the competition, the deadlines, and the hundred things that could go wrong if the company doesn’t move faster.

But before blaming the team for a lack of urgency, I asked him three questions.

1. Does your leadership team actually know what matters most right now?

If I interviewed each person separately, could they clearly tell me the three most important things they’re responsible for?

Not 10 priorities. Not a vague company goal.

The three things that matter most.

2. Do they know exactly what success looks like?

Are those priorities measurable?

“Improve sales” isn’t enough.

What number are we trying to hit? By when? What does done actually look like?

3. Do they have the resources required to get there?

Once you know the goal and the metric, work backward.

What actions need to happen to produce that result?

Then ask whether the person responsible actually has the people, budget, tools, information, authority, and time required to execute.

Only after those three things are clear does accountability become the real conversation.

Because if the team knows the priorities, understands the metrics, has the resources, and you’re consistently holding people accountable for the actions they committed to…

…and things still aren’t getting done?

Then you may actually have a performance problem.

But I think founders sometimes jump straight to “my team has no urgency” when the underlying issue is really unclear priorities, unclear ownership, poor goal setting, missing resources, or weak management systems.

Founders and managers: when someone on your team seems to lack urgency, how do you figure out whether it’s a people problem or a management problem?

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Why the Truth Thins as Your Company Grows

They’re lying to you.

Not maliciously, not even consciously.

But they’re hiding things, softening them. They nudge reality just enough that the core meaning is lost by the time it reaches you.

Who are these miscreants? Your employees.

That’s the sad pattern as your company grows. Teams expand. Managers multiply. Then come the managers of managers.

And as headcount grows, the average employee’s motivation shifts.

In a small team, what’s good for the company is good for everyone in it. Success is shared, so utilitarian thinking reigns.

But pass 30 employees, then 100, then 1,000, and a canyon opens between the company’s performance and an individual’s benefit.

The result? The scale tips from all-for-the-company toward all-for-me. Employees are more motivated to protect their own positions than to improve the business.

Cynical? Perhaps. But not wrong.

We’ve all met the employee who is more concerned with their bonus, budget authority, or title than with the company’s profitability. Do you think that person delivers the unvarnished truth up the chain of command when bad news strikes?

And it’s not just the selfish; even good people don’t.

Softening reality is rational self-preservation.

What’s a minor embellishment? No one really gets hurt, and I look a little better in front of my boss. It’s not even a 1% shift from the truth.

Until everyone does it.

The Lies Live Below the Dashboard

You have data, dashboards full of metrics. But one layer beneath every metric sits a human ready to explain the why behind the number.

That’s where the lies live. “So far, so good.” “Nothing concerning.”

So what do you do?

You can’t treat every member of your team as a spy with secrets to extract. But you’re not going to fully overcome human nature, either.

Humans evolved to survive, not to deliver perfectly objective status reports. For 300,000 years, survival meant staying in the tribe at all costs. Or, as the case may be, staying in your startup.

You can’t expect people to be perfectly honest, but you can design systems that encourage them to be.

• Gather witnesses. One person’s story is information. Two is data. Three is a pattern.
• Foster psychological safety. I’ve written about this before. People tell the truth when they believe honesty won’t be punished. They hide when they don’t.
• Admit when you’re wrong. A subset of safety, but worth calling out on its own. Leaders who show their fallibility make it easier for others to show theirs.

But there’s one habit that’s more important than all the others: Be a diagnostician.

Becoming a Diagnostician

One CEO told me his head of revenue had delivered bad news.

“We’re going to miss the quarter.”

I asked why.

“We didn’t close as many deals as we expected.”

That’s not a diagnosis; that’s a symptom.

That’s not enough information, I told him. Then I asked if I could pose a few more questions.

• Did we generate the number of new leads we intended to?
• Were there enough ICP leads among them?
• Did we hit our conversion rate from lead to closed deal?
• Did we get the upsells we expected?
• Did we see the average sale price we anticipated?

My CEO got the point.

“We missed revenue” (or “We beat revenue,” for that matter) is not actionable. It’s like telling a doctor, “I don’t feel well.” The diagnosis can only begin with asking better questions.

Those questions serve another purpose: They expose the 1% lies. “We did OK on conversion.” “Upsells were roughly on track.” “Lead volume was just about where we needed it.” Each of these statements sounds harmless. Each is just slightly softer than reality—about 1% softer.

A 1% Difference

The Titanic was only about half a percent off her intended course when she struck the iceberg.

Half a percent. That’s all it takes.

The danger isn’t any individual lie. It’s that each layer believes it’s passing along essentially the same information it received. Along the way, people instinctively smooth rough edges and avoid conflict. But like a game of telephone or making a photocopy of a photocopy, each iteration — each tiny adjustment — degrades the information. 

What starts as, “We’re going to miss the quarter because, despite having enough quality leads, we lost twice as many deals as expected to competitors we’d planned,” becomes, “We’re a little light this quarter.”

The message didn’t become false. It became harmless.

By the time it reaches you, you’re steering the company using a slightly incorrect map. Until one day, it isn’t so slight anymore.

One of the biggest bottlenecks I see as startups move from product market fit to repeatable, scalable sales is the founder.

Not because they are making bad decisions, but because too many decisions still require them to be involved.

A useful exercise is what we call the deletion test.

Look at every decision that crosses your desk this week and ask:

Did this actually need me?

Or did it land here because that is simply how the company has always operated?

If getting the decision wrong is relatively immaterial or easily reversible, delegate it.

Stepping out of a decision does not mean giving up control. The goal is to build a company where the right decisions can still get made when the founder is not in the room.

If everything has to wait for you, you are not just involved. You are creating a dependency that eventually slows the entire company down.

How many decisions in your company could move forward today without the founder?

If fundraising is another challenge on your plate, join Enjoy The Work General Partner Mike Lewis for a no cost fundraising workshop on August 26 at 8:30am PT. We’ll break down how founders can approach the raise with more structure and confidence.

Register here: https://luma.com/dao7ieny

A lot of the AI conversation right now is focused on LLMs, chatbots, copilots, writing emails, generating content, and making knowledge work faster.

But there’s another side of AI that may have an even bigger effect on everyday life: machines that actually take physical tasks off our plates.

Jonathan talks about using Tesla FSD and how much mental energy it has given back to him by removing much of the stress and tedium of driving. His daughter had a similar experience after buying a robotic lawnmower. It sounds like a small thing, but suddenly several hours of her week were available again for her kids, gardening, or anything else she would rather be doing.

That feels like one of the more compelling promises of AI.

Not necessarily helping us cram more productivity into every hour, but making mundane tasks disappear altogether.

Driving. Lawn care. Cleaning. Eventually, who knows how much of the repetitive work around the house.

What physical task would you most want AI to completely take off your plate?

Want more practical advice for building and funding your startup?

Join Enjoy The Work’s Fundraising Workshop on August 26 at 8:30am PT. There’s no cost to attend.

Register here: https://luma.com/dao7ieny

The fundraising narrative was done.

The pitch materials were ready.

The data room was organized.

The financial model was prepared.

We had gone through practically every question an investor might ask and practiced answering them honestly and clearly.

Then came a pretty simple question:

How is investor outreach going?

She had not sent any.

Not because she did not know what to say. Not because the investor list was unfinished. Not because there was another piece of fundraising prep left to do.

She was afraid.

Afraid of reaching out. Afraid of getting rejected. Afraid that the raise would not work. Afraid of disappointing everyone depending on her.

She actually felt embarrassed asking what to do about it because she thought it was a stupid question.

It is not.

A lot of the hardest founder problems are not tactical.

Sometimes you know exactly what you are supposed to do and still cannot get yourself to do it.

In this case, the advice was to start getting reps.

Instead of beginning with the most intimidating investors on the list, start with the people you already know. Investors you have some rapport with. Maybe someone who has invested before. Have the conversations. Get comfortable telling the story. Experience the rejection and realize you survive it.

Repetition does not magically remove every fear, but it makes the thing you are afraid of increasingly familiar.

This is also one of the reasons we started Taboo Topics at Enjoy The Work.

It is a monthly AMA for founders and CEOs to anonymously bring the questions they normally do not feel comfortable asking their board, investors, team, cofounder, or anyone else around the company.

Fundraising. Cofounder problems. Difficult employees. Board issues. Pivots. Burnout. Fear. Whatever is actually keeping you up at night.

There is no cost for founders to join, and there is no judgment attached to the question.

Ask whatever the hell you want.

Registration here.

Founders face hard problems all the time.

Sometimes they are questions. Sometimes they are full blown crises.

The problem is not always knowing what to ask. It is knowing where to turn for an honest answer.

It may not feel safe to bring your hardest question to your board member, your investor, your cofounder, your colleagues, your team, or even your spouse.

So where do you turn?

Introducing Taboo Topics

Taboo Topics is a new monthly AMA from Enjoy The Work where founders and CEOs can anonymously ask the questions they cannot ask anywhere else.

There is no presentation and no predetermined agenda.

You bring the problem. We talk about it honestly.

Maybe you are fighting with your cofounder.

Maybe you have an employee you know you need to fire, but you are unsure how to handle it.

Maybe a board member has become increasingly difficult.

Maybe you are scared about your next fundraise.

Maybe you are considering a pivot but are worried you’re quitting an idea too soon..

Whatever the question, you do not need to share your name, turn on your camera, or speak in front of the group.

You can submit your question and receive some help.

There Is Very Little We Have Not Seen

The Enjoy The Work team has spent decades building, operating, and advising companies.

We have worked with more than 270+ startups and supported founders through difficult board meetings, cofounder conflicts, executive departures, fundraising challenges, painful pivots, and the many other problems that come with running a company.

No question is too basic, complicated, or uncomfortable.

You do not need to arrive with the perfect question.

You only need to ask the one you have been sitting on.

Taboo Topics: August 11th, 8:30am PST

If there is a question you have been avoiding because you are not sure who is safe to ask, this is the room for it. Join anonymously, submit your question through chat, and hear how we would think through it.

There is no cost to attend**.** Save your seat here.

Let’s be honest: being a founder can be incredibly lonely.

The people around you may care about you, support you, and want your company to succeed. But that does not always make them safe people to talk to.

You may not want to tell your investor that you think their advice is wrong.

You may not want to tell your board that another board member is creating problems.

You may not want to tell your team that you are considering a pivot.

You may not want to tell your cofounder that you are not sure the relationship is working anymore.

And sometimes, you just need to ask a question without worrying about how it will change the way people see you.

That is why we created Taboo Topics.

Taboo Topics is a monthly virtual AMA from Enjoy The Work where founders and CEOs can ask the questions they cannot ask anywhere else.

The session is led by Jonathan Lowenhar, founder of Enjoy The Work, who has spent nearly 30 years operating companies and advising startup leaders through fundraising, management challenges, board issues, cofounder conflict, pivots, hiring, firing, and nearly every version of startup chaos.

There is no agenda.

You can join anonymously.

You can submit questions through the chat.

You can ask about the cofounder you are fighting with, the employee you may need to fire, the board member who has become a problem, the fundraise that is not going well, the pivot you are afraid to make, or the decision you keep putting off.

There is no such thing as a question that is too basic, too uncomfortable, or too messy.

There is no cost for founders to attend.

The first Taboo Topics AMA is coming up soon.

Register here:

https://luma.com/kbxpq4n2

We are also hosting a separate fundraising workshop for founders who want more tactical help preparing for a raise.

On August 26 at 8:30am Pacific Time, Mike Lewis, General Partner at Enjoy The Work, will lead a practical workshop on what fundraising actually requires beyond building a pitch deck.

Because fundraising is not one meeting, one introduction, or one great story.

It is a process.

You need to understand how to build an investor funnel, identify the right targets, prepare for the questions investors will ask, manage follow ups, handle objections, and maintain momentum throughout the raise.

This workshop is designed for founders who are preparing to raise, currently raising, or trying to understand why their existing process is not working.

There is also no cost to attend.

Register for the fundraising workshop here:

https://luma.com/dao7ieny

Founders do not need more vague advice.

They need a safe place to ask the real questions and practical tools they can use once they leave the room.

A useful way to think about decisions is to sort them into three categories: hats, haircuts, and tattoos.

Hat decisions are easy to reverse. Try something, see if it works, and change it if it does not.

Haircut decisions take longer to unwind. A wrong choice might cost you a few weeks or months, but it is still recoverable.

Tattoo decisions are the rare ones with lasting consequences. These are the one or two decisions each year that deserve deeper analysis, more data, and more time.

The problem is that many startup leaders treat every decision like a tattoo.

In reality, about 90% of decisions are worth ten minutes. Make the call, learn from the outcome, and keep moving.

For most decisions, the cost of waiting is higher than the cost of being wrong.

Have a difficult decision you cannot talk about publicly? Bring it to Taboo Topics, our monthly virtual AMA for startup founders, CEOs, and operators. Registration details are in the comments.

It may power your product. It may make your solution possible. But your customer does not care which model you use, how many agents you deploy, or how sophisticated your automation is.

They care about what changes for them.

Too many founders answer “What does your company do?” by leading with AI. The problem is that thousands of other startups are telling the exact same story. You become difficult to understand and even harder to remember.

A stronger story answers three questions:

Who is the person you are helping?

What painful problem are they experiencing?

How does their life or work improve because your company exists?

Your customer is the hero. Your technology is simply what enables the change.

Lead with the transformation, not the tool.

Few decisions weigh on a founder more than letting go of a long-time employee.

It becomes even harder when that person was there in the early days, performed well for years, and helped build the company.

But past performance cannot excuse ongoing underperformance.

When expectations have been clearly communicated, support has been provided, agreements have been documented, and the gap still does not close, the founder is no longer making the decision alone.

The employee is also making a choice.

They are choosing not to meet the expectations of the role, despite understanding what needs to change and what will happen if it does not.

This does not make the conversation easy. It does, however, help founders let go of the belief that they are solely responsible for the outcome.

You cannot do the work for someone else. You cannot force them to change. You can only provide clarity, support, accountability, and a fair opportunity to improve.

After that, their choices determine what happens next.

Founders often wish their teams would move faster, take more ownership, and get things done without needing to be pushed.

But hustle does not appear out of nowhere. It usually comes from having a clear game to play.

Think about a basketball court.

At the first level, people are casually shooting hoops. Nobody is keeping score, so nobody is particularly invested in the outcome.

At the second level, someone starts keeping score for them. The energy changes. People try harder because performance is now visible.

At the third level, the players are keeping score themselves. They understand the game, care about the result, and hold one another accountable. That is when you see real intensity and ownership.

Many companies never reach that third level for two reasons.

First, the team does not have clear metrics. People need to understand what success looks like at every stage of the business.

Second, the CEO is still responsible for collecting and reporting the numbers. The people who own the work should also own the reporting.

When your team understands the score and takes responsibility for tracking it, you no longer have to manufacture urgency for them.

Join our workshop tomorrow Startup Storytelling at no cost 8:45am PT!

One of the biggest mistakes growing companies make is assuming alignment already exists.

A leadership team may agree on the company’s goals at a surface level, but that does not necessarily mean everyone is aligned on where the company is going, why that direction matters, or how the team plans to get there.

At least once every 12 months, and ideally every six months, leadership teams should step back and answer:

What are we trying to achieve?

Why are we pursuing this direction?

What could prevent us from getting there?

Which challenge matters most right now?

What solution are we willing to test?

Once a path is chosen, the next step is execution. Set a clear timeframe, define forward looking indicators, and monitor whether the approach is producing the expected results.

Then decide whether to continue, adjust, or pivot.

The goal is not to create a perfect strategy. It is to make sure the leadership team is solving the same problem and learning from the same experiment.

At Enjoy The Work, we host no cost workshops for startup founders and CEOs covering topics including leadership, storytelling, fundraising, sales, and company building.

Explore our upcoming workshops here: https://luma.com/i4y37bnk