Monthly investor reports: How bad news can make you look awesome

As an investor, I’ve noticed that our best-performing companies tend to send investor reports frequently while the ones that are flailing or flatlined never do unless reminded.  As an entrepreneur, I know that it can be tough to convey bad news to your investors because you don’t want them to think less of you or be angry or disappointed.  Every time I had to write bad news to my investors when I was running LaunchBit, I would cringe a little bit before hitting the send button.

Originally posted by saynotosleepsummer

Actually, the opposite is true. I think less of entrepreneurs who never send any information because I think they have no hustle to ask for help when they need it nor are brave enough to own up to the situation.  On the other hand, if an entrepreneur rallies everyone together and says, “Hey look, this situation is not going well, can you all help with ABC?”, I really do want to help, and I think highly of an entrepreneur who can bring people together for a tough conversation.  Every company goes through tough times. There is always bad news, and you are not alone. If your investors have done multiple startup investments, they should know that very well.  One of my investors at LaunchBit once told me that tough situations are actually an opportunity to shine much more than when things are going well.  So, not only should you send investor reports to fulfill your fiduciary duty, it’s also a great opportunity to demonstrate what kind of an entrepreneur you are.

Originally posted by disneypixar

Moreover, it’s a way for your investors to get to know you as a person.  At the seed level, you often don’t have board meetings, and so you’ll want to get to know your investors personally through other means. A monthly investor report is a great avenue.  This makes it easier to ask for help, and investors want to help people they know well.  The worst situation to be in is to go MIA for 10 months and then out-of-the-blue ask your investors for a favor.  Whether it be intros to downstream investors or intros to other companies for business development or intros to job opportunities… sorry, if an investors doesn’t know you well enough, they aren’t going to be able to refer you or put in a good word.

Investor reports can be quick and simple and should only take at max 10 minutes to write.  You should send them at least monthly.  The Hustle writes one of the best investor reports I’ve seen and sends them weekly:


Here are 3 things you should make sure to include:

1. KPIs

Every company will have different KPIs they are tracking, but for most companies, this will revolve around revenue. At a minimum, include:

  • Last month’s revenue
  • OR if you are pure consumer company, DAUs / MAUs
  • Growth

Other potential metrics (depending on the nature of your business) may include:

  • Monthly leads
  • Churn / re-engagements / upsales

Some companies include a graph of their KPIs, which makes it easier to visualize.  If you don’t have one or it’s not useful to your company, don’t sweat it.  Investor reports do not need to be a chore.

2. How long are you in business?

You should also include your burn rate and runway.  Most entrepreneurs don’t realize that investors can potentially help you broker an acquisition or coach you through an acquisition if you can’t raise more money or get to profitability.  But, they cannot help if you have too little time left, which is often the case when most startups start to seek acquirers.

Similar to how you should allocate months for fundraising, you’ll need even more time to kick off relationships with would-be acquirers.  Sending an email out of the blue telling your investors that you have just 8 weeks of runway left and that you are only now seeking an acquisition is not helpful to anyone, and if you do find one, it will not be material.

Originally posted by bored-no-more

3. How can your investors help you?

Put your investors to work.  How can they help your business?  Do you need specific intros?  Do you need them to provide feedback on your deck for your next round?  Do you need help filling a specific role?  Do you need UX feedback?

You should ALWAYS ALWAYS ALWAYS have a call-to-action in your investor reports.  They may not all be able to help, but you should ask.

Investor reports can be used to connect people

As an aside, investor reports are also a way to be a connector.  Investors LOVE to network, and so you have the opportunity to connect all your investors with each other.  The Hustle, for example, will often host and email its investors about exclusive events. Later, whenever I run into a co-investor, we’ll often exchange a line or two about The Hustle, and everyone will feel good about themselves for being an investor.

Originally posted by alxbngala

I should note that their events are not fancy or costly at all.  It’s about the exclusive attendee list, not the actual food or drinks.  People can have a really good time with just $2 wine and simple cheese or pizza.  Exclusive events are also a good way for investors to bring in their friends, who will in turn also feel like they are part of something exclusive (and may even invest in your company).

Be transparent

Be transparent with your investors about your business.  They are already invested, and so you have nothing to hide, even if you have bad news. Sending reports on a monthly basis will make them feel closer to you, and they will be more invested in your personal success.

Why fundraising takes so long (for most entrepreneurs)

Techcrunch makes fundraising look like a breeze.  You just mosey on over to Silicon Valley, and there are dollar bills lining the road!

Originally posted by iheartswagdouble

Unfortunately, this is NOT reality.

While fundraising for my company LaunchBit, I was a wreck.  The actual process of going to meetings to talk about your company was not difficult, but the self-inflicted pressure to convert investors started to take a toll.  Compounding this with a lack of sleep made the process even more difficult.  It started getting harder when I started hearing “no” and still had to go into every meeting just as energetic as the last.

About 10 weeks into my fundraising process for LaunchBit, I had a nervous breakdown.  Literally a nervous breakdown.  My body felt like it was being pricked with pins all over all the time.  Obviously, no one was actually jabbing pins into me, but it was annoying, and I was unable to sleep at night  (not to mention, it simply felt weird).

Originally posted by hannah-sieberling

I went to see several physicians, including some of the best specialists in the country, and no one could figure out what was wrong.  Because this nervous issue started around the time I started fundraising, I decided that it was probably related.  So, I paused fundraising.  And, of course, the problem went away.  Fundraising is an incredibly stressful and lonely process that is like a rite of passage for startup CEOs.

Eventually, we raised over $1M in that round (TC reported $960k here). It sounded like a walk in the park to get name investors into the round, but in reality, it was super hard and took a long time to raise.

These days, I hear a lot of entrepreneurs saying, “Oh, my raise will be hard because 2016 is going to be tough for entrepreneurs.”  Honestly, no matter what the economy is or what space you’re in, fundraising is ALMOST ALWAYS F***ING TOUGH as a first-time entrepreneur.

So why is it so hard, and why does it take so long?

Here are some common issues:

1. Your story is not yet compelling

Maybe your story is OK, but if there’s no wow-factor to get people really excited, then it’s not going to be good enough to get investment dollars.  You’ll need

  • a wow product
  • wow results
  • a wow team
  • a strong and/or unusual differentiator
  • interesting insight

At least one of these has to be above and beyond amazing to make your story awesome.

Originally posted by dell

2. There are discrepancies in your story

I’m not talking about lying — though it goes without saying that you should not lie about your business!  Sometimes you are so close to your business, you do not even realize what looks off.

For example, if you have a marquee list of enterprise companies as your customers but are only generating $10k/month in revenue, you need a good explanation for why this is the case when these customers could be paying you so much more.

It could be as simple as stating that your customers are right now just piloting or beta testing your product, but your whole story needs to be consistent.

3. You cannot yet answer questions well

Before you start fundraising, you should be able to answer all common fundraising questions well.

In addition to this list, you’ll also be asked about your vision, where you see the business going, and how you see the future.  This is often difficult for a lot of first-time entrepreneurs because you are so heads down in the weeds just trying to fight fires.  And who the f*** knows what will happen in 10 years?  You don’t need to be right, but you do need to have a vision for the world as the CEO.

You will also be asked about your next hires and what you’ll do with the money. Of course, you will also be asked a hodgepodge of questions you cannot anticipate a priori.

4. You do not seem confident in your pitch

Fundraising is an odd beast for first-time entrepreneurs.  On one hand, it feels like a sales game because you are trying to sell an investor on your business.  On the other hand, it is a lot like a power struggle.  You must assert yourself and show that you know how to run a company.

Unfortunately, there are a ton of great entrepreneurs who are not naturally high energy or confident-seeming even if they are actually confident, great leaders in quieter ways.  You’ll need to exude high energy and high volume to give an investor confidence that you can run this business.

This may mean experimenting with how you speak, your body language, what you wear, and your mannerisms.

Originally posted by disneypixar

5. Investors have information concerning your business that you’re not privy to

Even if you can solve for the points above, there’s a lot of information that investors know that entrepreneurs don’t.

Investors may:

  • See way too many pitches in your space and/or think the market is crowded (e.g. on-demand food delivery)
  • Have had a bad experience with a company in a similar space or business 7 years ago and don’t want to touch that space again (e.g. travel)
  • Know just how big competitor X is and how much funding they have secretly raised and are concerned that you are too closely related

In your first 20 meetings, your job is to tease out all of these concerns.  You need to figure out what is wrong quickly so that you can fix these issues at subsequent fundraising meetings.

However, it’s important to avoid have pitch-whiplash and change your pitch based on every little comment.  But if three investors mention the same concern, then you should be self-aware enough to change your pitch and investor conversations OR change the types of investors you pitch to.  Test new ways to address concerns in subsequent meetings.

Fundraising takes a long time because you need to meet with a lot of investors in order to refine your pitch, how you pitch, and find investor-business fit.  Unfortunately, there are just no shortcuts.

How do seed VCs pick their investments?

On Friday, I spent a couple of hours at my alma mater talking with student entrepreneurs about their companies.  When I got there, most of them wanted to know how VCs pick their investments and what 500 Startups look for.


I didn’t answer this.

Instead, I said, “Let’s pretend we’re all forming a VC firm right now.  And there’s an entrepreneur coming into the room in 10 minutes.  What questions would you ask him/her to decide if you’re going to invest?”

I wasn’t sure what people would come up with, but here’s the list of questions the group collectively came up with in 10 minutes with my commentary in brackets:


  • Do you have a strong team? [Get more specific – what does that mean?]
  • Does the team have particular domain knowledge or expertise?
  • Have the co-founders worked together before?
  • Can they change directions quickly if needed and make fast, difficult decisions?
  • [What about perseverance, grit, tenacity?]
Originally posted by ixaurore

Customers and traction

  • Do they have product or market fit? [Get more specific – what questions would you ask to figure this out?]
  • Do they have customers? How many?
  • Who exactly is the customer?
  • Are they paying? If so how much?
  • How frequently are customers buying or using? [Or churning]
  • How much does it cost to get a customer?
  • What is a customer worth? [lifetime value]
  • [How much revenue are you making and how has this changed over the last few months? What are your margins?]
  • [How are they getting customers?  What customer acquisition channels have they tried or not tried ?]
  • [Is this growing? How quickly?]
Originally posted by littlehorrorshop


  • What is the market size? [I have disputes about this one but that is a topic for another post]

Problem and solution

  • What specific problem are you solving?
  • [Why are you doing this?  Motivation?]
  • What makes your solution unique or differentiated?
  • Is there any special tech or IP here? [In many cases, probably not worth asking]
  • What is your unfair advantage? [Often there is little-to-none in the beginning but worth asking about this to see how entrepreneurs think about this and see if there is special domain knowledge or special relationships & partnerships]
Originally posted by amidallas


  • What is the cost of equity ownership? [May or may not ask this depending on if our hypothetical VC firm leads rounds or not]
  • [What is a team’s burn rate?]

Obviously, if we had brought in a real entrepreneur to talk with, the list would also include more specific questions about the particular business and/or how the product works.

I was pretty impressed by this laundry list of questions they generated – not bad for 10 minutes!  It looks like I can go retire on a beach somewhere.


How many entrepreneurs are doing their pitch decks all wrong

Even though there are a lot of web resources on how to put together a pitch deck for seed-stage companies, most don’t address how many decks you need and for what purpose. If you are fundraising, you’ll need at least 2 decks:

  1. An email deck
  2. An in-person meeting deck

If you are participating in a Demo Day with an accelerator, you’ll also need a Demo Day deck.

Originally posted by theweekmagazine

Obviously all your decks will be similar, since you are pitching the same company!  All of your decks should:

  • Be compelling – lead with your strongest points first! If it’s team, then lead with team.  If it’s traction, lead with traction.  If it’s a big problem, and you have an unusual solution, go with that.
  • Tell a story – this is not just a series of facts.  The slides must flow together.
  • Be visual  – i.e. verbalize, don’t make an investor read words.
  • Be simple – an investor should understand the slide in 1-2 seconds; don’t make him/her think.
  • Include your contact information so that people can contact you!
Originally posted by the-office-daily

But, there are some major differences…

What is an email deck?

An email deck is what you’ll email to investors if they ask to see a deck first before setting up a meeting with you.

There should be enough information here to be compelling enough to take a meeting with you. BUT, not too much such that they can decide NOT to take a meeting with you.  Keep in mind that many investors could (will!) forward this to other people, so don’t put anything too confidential in here.

Examples of what to put in (not in this order per se):

  • Problem you’re solving
  • Your solution
  • Traction – key performance indicators (could be MRR, growth, users – whatever makes the most sense for your business)
  • Market
  • Team

The purpose of the email deck is to get a meeting – that’s it.  So, you should include facts about your business that will be compelling to get you that meeting and nothing more.

The flip-side is that you shouldn’t include too much – specifically, anything that can be nitpicked.  These are some things I wouldn’t include in an email deck include:

  • How many people you are hiring
  • Financial projections or forecasts

These are hypothetical. The number of people you hire could change, and if an investor thinks you should hire 5 sales people instead of 4, you shouldn’t let that be what stops you from getting a meeting.  Similarly, if you are projecting too high or too low of a revenue number for next year, an investor may think that you are unrealistic or not ambitious enough, and you are not even there to defend your argument when he/she reads your deck.

Realistically, an investor will spend only 10 seconds looking at your deck, so it has to be understandable and concise.  It’s ok, if he / she only understands the gist.  The meeting will allow for detailed discussion.

Lastly, an email deck serves to provide context.  Sometimes an investor you’ve already met with may ask for an email deck so that he/she can send the opportunity to other partners / investors at his / her firm so that they can get context before meeting with you.

What is an in-person meeting deck?

An in-person meeting deck has the meat.  Lots of great people have written about what slides you should have for this deck.  You can find great resources herehere, and here (among many other places).  I don’t need to dive into this in detail.

In short, an in-person meeting deck should have ~10 high level slides with appendix slides that dive into the weeds.  In addition to the other slides from your email deck, include your business model and 1-2 key unit economics (LTV, CAC, churn, etc.).

Originally posted by nasty-parlour-trick

Even for this deck, you’ll want to still keep the slides at a high level.  If an investor asks to dive into the weeds on certain areas, then you can guide him/her to the appendix slides you’ve prepared and fully cover a topic before continuing on.  Some investors prefer to dive into product questions and others really want to dive into customer acquisition channels and unit metrics.  You’ll want to have lots of appendix slides to cater to different audiences, but most of the time, you won’t dive into all of them.

If you’re meeting with an angel investor, this first meeting may be all that you need to secure funding.  But, if you are meeting with a VC, the purpose of this deck is to get the next meeting.  (Be sure you ask questions to understand how an investor decides to invest and what his/her process is.)  At a firm that moves quickly, that next meeting could be an all-partner meeting, which is typically the last meeting needed to make a decision (for seed-stage).

Go get ‘em!

What questions should you ask seed investors?

I’ve ragged on investors quite a bit in my recent posts here and here.

But fundraising meetings are a two-way street.  Entrepreneurs also need to do a much better job pitching.  Specifically, I’ve noticed that many first-time entrepreneurs do not ask any questions.  This is a serious mistake.  Entrepreneurs should learn everything they can about an investor.  Taking investor dollars shouldn’t be done lightly.

Originally posted by urbanrealism

You don’t want to take money from bad apples because down the road when things get tough, investors can:

  • Call their convertible note
  • Potentially replace you (depending on the equity and board situation)
  • Threaten litigation (even if they have no case)
  • And most importantly, be a big pain in the ass and call you all the time

You are looking for a relationship – not just money.

Originally posted by aliens-bro

Before taking an investor meeting (or even reaching out), you should definitely do your homework and research investors.  Make sure to reach out to investors who are actually a good fit for your business (stage, sector, amount, what they look for, etc).  Most websites will spell this all out – especially newer microfunds who are trying to differentiate themselves in the market by going after a specific niche.

In addition, here’s a list of questions you should ask investors when you meet them:

  • How big is your fund? (for VCs)
  • Where are you in your fund?  (for VCs)
  • When will you need to fundraise again? (for VCs)
  • Do you lead rounds? (for VCs)
  • What is your typical check size?
  • Do you reserve capital for follow-on?

This gives you a sense of how much money you can raise from a given firm or individual.  This is really key because there are a lot of investors out there who have no money but are still taking meetings.  It’s OK to take a meeting with an investor who has no money to invest, but you should know that they won’t be able to come into your round until they have raised money so your meeting might not lead to anything.

Originally posted by odditymall

Understanding how much is allocated for follow-on investments also gives you a sense of how much money is left in a fund.  If a fund is $10M and two-thirds is reserved for follow-on, then in practice, there’s $3M for first checks.  If the firm has already deployed $2M, you know that your chances of getting a first-check is slim…

In general, it’s slightly easier to raise from funds that have just raised a fund.  They have a lot of money that needs to be deployed, and so they are more eager to invest.  In contrast, when there are fewer dollars left to deploy, those last dollars will be extremely competitive.

You should find out an investors’ cadence:

  • How many seed deals have you done in the last 6 months?
  • How many seed deals do you anticipate doing in the next 6 months?
  • How long does your process typically take?

And how decisions are made:

  • What is involved in your process?
  • Who is the decision maker?  (for VCs, although sometimes angels need to consult their families or friends)

By the end of the meeting, you should understand

  • Everything about an investor’s decision making process
  • Whether you have a champion to take this to the decision makers (whether it be partners at a firm or their family)
  • What the concerns are with your business in their eyes
  • What the CONCRETE next steps are

If you do not have answers to ALL of these questions, keep asking questions…

Attention investors: can you just be upfront with your thoughts? K thx bye.

The first time I ever tried to fundraise, I was completely clueless.  My team had built a highly technical product that allowed consumers to co-browse with each other, but we had no customers or users.

Originally posted by chloaw

A lot of investors turned me down, but I didn’t even realize it because they were not clear in their rejections.  Investors would tell me:

“Oh this is a very interesting product.  Let’s keep in touch.”

“The technology is quite interesting….thank you for showing it to us.”

As a naive founder, initially I did not push to get to a call-to-action or to learn what the next steps should be.  I had no idea how close I was to successfully raising investor dollars (read: not at all).

As I met with more investors, eventually, in my frustration of not getting anywhere, I realized that I needed to push harder to find out what investors really thought and whether they were going to invest in my company soon.

Still, investors were quite nebulous in their thoughts on my company.  I remember this one phone call very clearly:

“So, are you going to invest?” (I was not sure how to ask this in a great way, so the first time I asked it, I was pretty blunt because I just needed to know the answer.)

“Well, it’s an interesting product.  Let’s chat again in a couple of months.”

“I’m not sure I understand; is that a yes or a no?”

“It’s a no for now.”

Originally posted by yaasbabe

That conversation was just the first step in my becoming a savvier fundraiser, but it took many, many more missteps and poorly-run fundraising meetings for me to eventually understand how this game is played.

Most investors are simply not upfront with their true thoughts because they are afraid to reject entrepreneurs.  They think entrepreneurs will not come back to them later when they have made more progress or have found a better business.  I find that this is particularly common behavior amongst investors who have never been founders.  So this is the type of vacuous email you typically receive as an entrepreneur:



This is a big mistake in my opinion.  Although, founders should also be less clueless on how to run investor meetings and should ask good questions (something I hope to change with this blog), if investors were more upfront with their true thoughts and opinions, founders would find that feedback valuable.

Great founders can take feedback well and can learn and adapt quickly.  The investors I have the greatest respect for are the ones who were candid with me about my company – whether they invested or not – without my having to pry their thoughts out of them.

Originally posted by gurl

I realize it is a tall order to ask investors to be explicit with their feedback.  It’s not a fun job to send tons of rejection emails everyday.  When I first started investing, I was unsure what to write in a rejection email, and so I asked Dave McClure for advice.  He told me to frame my emails positively – what it would take for me to invest?

This has been one of the best pieces of advice I’ve received in joining Venture Capital.  So, I now write entrepreneurs emails like this:


Although, it’s still not fun to be the bearer of bad news, it causes entrepreneurs to come back to me later when they’ve fixed some of my concerns.  This helps me see how quickly teams can learn and adapt, which is one of the best indicators of a team.

Plus, we end up having productive conversations about their progress which actually *helps* me build a relationship with entrepreneurs.

Entrepreneurs: what has been the most helpful “rejection” you’ve received?  Tweet @dunkhippo33.