You should have 4 fundraising plans

When I was raising money for LaunchBit, sometimes my conversations with investors would go something like this:

Investor: So how much are you raising?

me: We’re raising $750k.

Investor: Really?  Why so little?  You should be raising $2M+ or even a series A.

Of course, the first thought in my head was, “Wtf?  I’m struggling here to just raise anything!”  But, of course, I couldn’t say that out loud, because then the investor might not want to back me.

Originally posted by gabys42

This kind of conversation happens a lot, though.  So what do you do?  You need to prepare four fundraising plans.  What would you do if you raise:

  • $0?
  • Below your target raise?
  • Your target raise?
  • Above your target raise?

What happens if you can’t raise at all?

First, let’s address the easiest scenario – what if you raise $0?  Do you bootstrap and attempt to raise again when you have made more progress?  Do you have family and friends who can help float you?

This is a situation you should always be prepared for whether you are actively fundraising or not.  Investors will likely even ask you this question as a hypothetical scenario to understand how you think about your business.

Investors want to invest in growth

The trickier situation is to prepare for the remaining three fundraising plans.

Taking a step back, it’s worthwhile to know that regardless of your stage, investors want to invest in growth.  To be clear, growth means increased revenue or increased number of users or customers (or both!).  It does NOT mean growth of your employee base!

Originally posted by rukudzom

With that in mind, you should understand clearly what lower and upper bound raises you’d be wiling to chase.  In other words, your lower and upper bound numbers should ALWAYS be raises where you could put the money to good use to grow the company.  Here’s a quick thought experiment:

For your upper bound number, if someone offered to invest $50M into your company, would you know how to deploy that money efficiently to increase your growth tremendously?

For nearly all seed stage companies, the answer is no.  You could certainly hire more people with $50M, but again, growth is not measured in terms of employees.  It’s measured in revenue results.  Could you turn $50M into $1B in revenue in the next 2 years?  At the seed stage, you don’t have enough information about the levers of your business to know how to do this.

At the seed stage, you might have some sense of 1 or maybe 2 customer acquisition channels that are working (at least for the time being).  You should use your data from these experiments to figure out the maximum amount of money that you’d feel confident throwing into these channels to yield great growth.  Great growth in venture investors’ eyes is often 30% MoM growth or higher depending on your baseline revenue and the space or business you’re in.

Originally posted by gabrielmismash

Similarly, you’ll want to repeat the same exercise for your lower bound number.  If you were to spend 2 months dedicated to fundraising, what is the smallest investment number that would be worthwhile raising such that you could immediately pour that money into growth for your business?

Consider growth, 18 months of runway, buffer, and milestones

Ok, so now you have a lower bound and an upper bound number for your raise.

Now, to pick your target raise (which is in between the lower and upper bounds), you should figure out the number in this range that will:

  • Give you 18 months of runway
  • Multiply that number by 2 for buffer, because things always take twice as long to achieve
  • And also gets you to the next milestone in that timeframe

If your next milestone is a series A round, you should remember that series A milestones tend to be in the $2M-$3M net revenue runrate range these days.  This is a step up from the $1M runrate milestone that people touted a few years back.

Originally posted by find-a-reaction-gif

If your next milestone is a seed-plus round, you should know that a lot of startups chasing after seed-plus rounds (i.e. what the old series A rounds used to be) tend to be doing $500k – $1M net revenue runrate range today.

Note: Marketplace and ecommerce companies, GMV is NOT REVENUE.  

I’m sure the milestone targets will only rise as more people become entrepreneurs and competition for limited investor dollars increases.  So, aim to err on the side of being more conservative around what milestones you need to hit.  Also, if you are in a crowded space (e.g. on-demand food), you will need to go above-and-beyond and surpass these rough milestone guidelines to demonstrate you can rise above the noise.

More on milestones in a subsequent post, but the bottom line is that you should make sure to pick a target raise number that hits these criteria. You do not want to fall short and be dismissed at the next round for not having accomplished enough in a timely manner because you raised too little money.

Form a concrete plan

So, now you need to prepare a concrete plan for all three raise numbers.  You should figure out:

  • Who you would hire?  (if you have specific names of people in mind who want to join you, this is even better)
  • How you would deploy the money for growth?  (the more specifics, the better)
  • What milestones would you hit? And on what timeframe?
  • What would the payback period of your customer acquisition be? (if you know)
Originally posted by veggietalesgifs

Four plans give you optionality

Now that you know what you’ll do in each of these four scenarios, you have a lot more optionality.  Although you will still go out and discuss your target raise, if an investor asks you why you aren’t raising more, you can always say, “Well, actually, I’ve prepared a plan around X, and if we have the interest, we’ll certainly opt to do more with a larger raise.”  By preparing details around how you’d use the larger raise, an investor may actually offer to invest at that larger amount.

Alternatively, let’s say an investor says, “I really don’t see how you’ll hit your target raise, and if you’ll fall short of your raise, I’ll lose my money.  I’m out.”  You’ll have a good response to this as well – you can describe what happens if you raise near $0 and also what you can achieve with your lower bound raise.

Alright, go get ‘em!

How to find email addresses to cold-email (for free)?

I’ve previously written about how to write cold-emails and why to cold-email people like Steve Ballmer.  But, how do you find Steve Ballmer’s contact information?

1) Use Rapportive

Cristina Cordova, who does Business Development at Stripe, writes about using Rapportive to guess a person’s email address.  Having tried this trick a number of times, it’s quite effective.


Ok, so let’s use this method with Steve Ballmer.  After a bit of quick guessing.,, etc, I hit gold.  But, let’s say this method didn’t work.

2) Message via LinkedIn 

Even using the free version of LinkedIn, you can often message people without being a first connection with them.  If you know who you want to email, check out his/her LinkedIn profile.  Find the groups he/she has joined.  Join those groups.  You can very often message people who are in the same group.

Even better is if a mutual contact feels comfortable introducing you over email or via LinkedIn.


Applying this technique to find Steve Ballmer’s email address, it appears he has 0 contacts on LinkedIn, so we have no known friends in common.  And, he does not belong to any groups.  So this method was a bust this time.

3) Search through online alumni networks

If you attended a school that has an online alumni directory, you can easily find contact information of alums.  Didn’t attend Harvard or Yale?  Beg and plead with a friend to help you look through his/her account.


Applying this technique to Steve Ballmer, who attended both Harvard and Stanford, I was able to find an email address and a phone number for him (not shown on screen).

But, let’s say we didn’t.  Moving on…

4) Search on Google

When in doubt, guess on Google.  These days, email addresses of high-level people, can be found on the web.  High-level people will often give presentations and post their slides on the internet.  It’s common to post contact information on the last slide.

But, beyond that, if a company has ever had a problem or an issue (all companies do), high level executives will often post their email address in forums asking unhappy or confused customers to email them.

You can use the same technique that Cristina uses with Rapportive to guess email addresses on Google.  Let’s guess Steve Ballmer’s email address.


You can see that he gave out his email address to the public at a Microsoft event on 2007.

So, 3 of 4 of these methods have successfully given us Steve Ballmer’s email address.  But, what if we still couldn’t figure it out?  You may argue that Steve Ballmer has a much greater web presence than perhaps an executive at a non-tech company.  This leads me to my last point.

If all else fails, guess

If we could not find Steve Ballmer’s address, I would try to look for other employees who work at Microsoft to see if there are patterns in the structure of their email addresses.  A lot of companies use a standard pattern such as or or etc.  I would then take my best guess and send an email to that address.

But, I would NOT email 7 different guesses like this:


This cold-email I received looked so desperate!  If you guess incorrectly and it bounces, you can try again with a different guess.  And, even if your email goes to the wrong person, it can still make its way to the right person.  I once guessed an email address incorrectly, and recipient replied to me and included the right person I wanted to reach on that email.

What methods do you use to find email addresses of people you want to reach?

Who is the best person to ask for an investor intro?

In my last post, I talked about how to write an email requesting an investor intro, but I didn’t talk about whom you should ask.

tl;dr – in order, the strongest referrals to investors come from:

  1. Portfolio founders who have raised recently from that investor (i.e. not enough bad stuff has happened at their company to make the investor disillusioned w/ the entrepreneur) OR past portfolio founders who have made the investor money
  2. Investors in your company
  3. Personal connections
  4. Other investors / founders / former colleagues of theirs (note: exercise caution here)
Originally posted by theweekmagazine

When I was raising money for LaunchBit and I wanted to reach investor John Doe, I used LinkedIn to see who knew him.  Very often, I was a 2nd degree connection to John Doe through a number of people including:

  • Investor Billy Bob – someone I’d just pitched; jury still out on whether he’d fund LaunchBit
  • Entrepreneur Sarah Smith – someone I’d known for years who is really nice
  • Entrepreneur Erlich Bachmann – a well-known entrepreneur whom I’d met once at a startup party
  • Investor Christine Tsai – an investor in LaunchBit whom I’d known for years and even worked together with at Google
  • Entrepreneur Jane Do – an entrepreneur whom I’d met a couple times before at various startup circles and had just raised money from John Doe

Who is best to ask for a referral?

Obviously, this situation wasn’t super ideal.  In an ideal world, my best friend would be a super successful entrepreneur who would know John Doe and could make an intro, but when you’re asking for potentially hundreds of investor intros – yes hundreds (more on that later), this is not going to be the case a lot of the time.

Originally posted by kaithebluh

The seemingly obvious person here is Christine Tsai because she’s known me for quite a while and also invested in LaunchBit.  I could ask her.  You certainly should leverage existing investors.  So, I’d ask Christine.

Investor Christine

But, Christine is also an investor and pings potential co-investors all the time about deals, so what is the weight of her recommendation?  In fact, to a certain extent, it’s her job to sell her companies to downstream investors…so will LaunchBit stand out to John Doe amidst all her other referrals?

I should probably also get a second intro in parallel in case Christine takes a long time to do this intro AND as a way to stand out once her email hits John’s inbox.  If he sees a couple of people mentioning my company, that would remind him about us.

Investor Billy Bob

I definitely shouldn’t pick Billy Bob.  Even though I’ve talked with him most recently, I don’t know yet what he thinks about LaunchBit.  I don’t know if he’d be an advocate, and I’m not sure if he’d recommend us.  In fact, if he and John Doe were to discuss the deal, they could both end up talking each other out of it, as often happens when investors get together.  Ideally, they should come to their own independent conclusions about my company.

Entrepreneur Sarah

I could ping Sarah, since she’s always been super helpful and nice to me.  But, I should find out first how she knows John.  Did she pitch John and did he say no to her company?  Just because John and Sarah are connected via LinkedIn, I’m not sure what John thinks of Sarah, so a recommendation from her may or may not be a positive signal.

Entrepreneur Erlich

I haven’t talked with Erlich in years and only met him once at a party.  Like Sarah, I don’t know what John thinks of Erlich and vice-versa.  Since Erlich is successful, chances are that John respects him professionally on some level.  However, I’ll need to pitch Erlich and sell Erlich first on LaunchBit before talking with John, and since it’s been years since I’ve spoken with him, that might be tough.  Erlich is probably not my first go-to person after Christine if I have a choice, but he could be a last resort.

Originally posted by glitterdwarf

Entrepreneur Jane

Finally, there’s Jane, who just raised money from John.  Based on that signal alone, I know that John thinks highly of Jane and is still really excited about her business.  Like Erlich, I would need to sell Jane first on LaunchBit so that she could sell John on meeting with me.  Note: you are always selling – even if someone isn’t an investor!  They can often help you sell your company to investors or other great contacts.  Even though Jane isn’t famous, she’s a much better person to get a referral from over Erlich because I already know that John not only respects Jane for her work, he’s so committed that he invested in her work.


In this situation, I would ping Christine and in parallel, also ping Jane to discuss with her briefly about whether she thinks it makes sense for me to connect with John about LaunchBit and whether she can help me with that introduction.

Getting investor intros is a game of hustle that often takes a long time.  Approach the best people who can help sell your company and whom an investor thinks highly of.  Approach multiple people.  And always be selling – even to people who are not investors.

How to ask for an investor intro?

The VC world is very relationship-based.  This is changing, but many VCs prefer to meet with founders who come highly recommended by close connections.  The problem is that well-connected people who can help with introductions are often inundated with requests.

So, even if you ask your well-networked friend who is a total supporter of you and your company for an intro, it could still take him/her a couple of weeks to get to your intro request.

Originally posted by theweekmagazine

Unfortunately, as a founder, you really don’t have time to wait a couple of weeks just to get an intro.  And sometimes, you need to get an intro from one well-connected friend to another well-connected friend who can do a strong intro for you.  And that could take weeks!

So what do you do?

You need to make it super easy – as easy as possible – for people to do intros for you.  Here’s how.

1. First briefly ask your friend or acquaintance if they wouldn’t mind pinging Investor John Doe with your request

Tell your friend that you’re raising a round, and you’re interested in talking with Investor John Doe to gauge his interest in your business.  Ask your friend if he/she wouldn’t mind pinging John Doe with your request to meet up briefly.  Tell your friend/ or acquaintance that if that’s cool, you’ll send a separate email with the request.

Originally posted by mynamestartswithaletter

2. Write an email that makes it super easy to forward to John Doe

THIS IS SUPER CRITICAL.  If your referrer needs to think, write, or spend any more than 5 seconds on your intro, then it will not get done for weeks.

Write the email from you.  DO NOT TRY TO WRITE THE EMAIL FROM THE PERSPECTIVE OF YOUR REFERRER.  It will not be in his/her voice, and he/she will end up spending a ton of time editing it.

Here’s an example of a very good email requesting an investor-intro from one our batch founders (with details of the business changed for confidentiality reasons):

Hi Elizabeth,

Thank you in advance for sending this to Martha at BigCrazy VC. We’re raising our seed round and I’d like to get her thoughts on HippoCo. Here’s a quick background:

The $180 billion hippo education market is antiquated and ripe for disruption:

1. Highly fragmented – over 80% of hippo education is distributed through mom and pop stores and only 20% is branded, elite hippo education

2. Structurally inefficient – archaic supply chains require significant working capital for inventory and long lead times to launch new classes / educational content for hippos

3. Un-segmented – Product offerings are split mainly into expensive, elite hippo education or cheap made-up content for hippos with nothing in-between

HippoCo has addressed these issues and created a direct-to-consumer educational brand that offers affordable, useful educational content for the millennial hippo.  We co-design and market new educational products in collaboration with top teachers at traditional hippo schools.

The results are validating our model and popularity with hippos:

  • Annualized revenue: $900K USD, growing +70% QoQ
  • Margins: 50% – 60%
  • Strong unit economics: CAC: $25, 25% repeat purchase rate in the past 6 months

Founders are third generation hippo teachers and technologists from the Bay Area.

My Best,


Originally posted by tinsoftware

When I forward an email, I simply add my note to the top to give my thoughts and perspective on the founder and/or company.  The email above covers everything that needs to be said, including context (why the founder wants to talk with Martha) as well as key information about the business (KPIs and a description).

These are the biggest mistakes entrepreneurs make when asking for intros, which delays them:

  • Not providing any context (why the hell do you want to meet?)
  • Sending a blurb that doesn’t say anything (vacuous)
  • Neglecting to include a couple of KPIs
  • Asking for 9 intros but only sending one email that can be forwarded (you should create a SEPARATE email for each intro you want)

If you do any of these bullets, it means your referrer has to THINK about what additional information to add OR do a lot of copying and pasting.

These may seem like silly deal breakers, but if each task takes 5 minutes, and your referrer is inundated with even just 10 requests like this a day, it will end up taking him/her an hour to fulfill this.  This means that your intro requests will end up being neglected for a couple of weeks.

3. Follow up. 

If you don’t hear back from your friend/acquaintance within 5 days, follow up.  It may be that he/she forgot to reach out to the investor you want to approach. Or, it may be that the investor never got back to your referrer.

People’s inboxes get buried quickly, so don’t feel bad about following up!

Originally posted by theyellowtracksuit

4. Optional: Let your referrer know how things went

Lastly, assuming you get connected, let your referrer know how things went.  It goes without saying that you might like to thank your referrer at some point during this process.

If you end up sealing a deal with the investor, make sure to mention that to your referrer.

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.