The 8 Types of VC Fund Investors

I’d raised money for startups before. How different could it be? Just add a zero or two to the ask, right?

It turns out that raising money for a venture fund is a heck of a lot different than raising money for your startup… and certainly not any simpler.

You see, angel & VC investors are all pretty similar when it comes right down to it; we want you to make us money. Show us good odds (by startup standards) to make a lot of money and we’re in.

Fund investors are far more complicated. Prospective Limited Partners (“LPs”) have a variety of motivations and each type of LP needs to be approached differently. Here are the 8 different types of LPs I have encountered in the course of raising money for the fund DreamIt uses to invest in the startups we accelerate:

1. Maximizers
2. Allocators
3. Institutionals
4. Pipeline Fillers
5. Strategics
6. Economic Developers
7. Impactors
8. Fund of Funds

Type: Maximizers
Winning strategy: Show them the money

Maximizers are the most like angel investors. They are sector agnostic; they don’t care if the investment is in real estate, a cupcake shop, a tech startup, or your fund – you are competing with every other opportunity out there for their investment dollar. They just want the biggest bang for their buck. To win, you need to show that your fund’s combination of risk, reward, and time frame is the best. Don’t waste too much time on strategic differentiation. Cut to the chase and stress the overall performance of your sector vs. other sectors, your team’s past performance and other relevant experience, and (if you’ve already started investing) the performance and potential of the companies already in your fund’s portfolio.

Type: Allocators
Winning strategy: Be best in class

Allocators are typically individuals or family offices who take a top-down view of their portfolio and have decided that they want a certain amount of “exposure” to VC. You have to show them that you are the best option in your venture asset class. It often helps if you can redefine the class somewhat. Make it narrower and it’s easier for them to see how you come out on top. For instance, DreamIt doesn’t simply position itself as a VC fund investment. We are angel stage investors and in that extremely early stage there aren’t many alternatives; there are just a handful of other top accelerators with funds. Beyond those, the Allocators’ only other options are second tier accelerators and direct angel investing. Allocators are allergic to the former and don’t have the time or skills for the latter.

Note that, while you don’t have to sell your sector to Allocators, it does help if you can show that your sub-sector outperforms. Fortunately for us, overall VC returns for the past decade plus have been pretty dismal whereas early stage / angel returns have been stellar.

Type: Institutionals
Winning strategy: Be best in class… and be patient

Institutionals (e.g., pension funds, endowments, insurance companies) are essentially very large Allocators. They are run by professionals and tend to have standard (and often slow & painfully thorough) due diligence processes, in part because they tend to be more conservative and focus heavily on preserving capital. Their challenge is to keep a lot of money at work at all times. Small investments are the same amount of work to assess for them as large ones are but even super returns just don’t move the needle for them unless their initial investment is big enough. At the same time, most institutions don’t want to represent more than 10% of your fund. So if their minimum check size is $5M and you have a sub $50M fund, you are likely wasting your time.

One caveat: Pre-existing relationships are very important to Institutionals so if you expect that your next fund will be in their strike zone, it pays to set aside some time to meet them anyway and to start building the relationship,

Type: Pipeline Fillers
Winning strategy: Create portfolio envy

Pipeline Fillers are looking for dealflow. They may be later stage VC or PE funds who know that it is extremely hard to get into the hottest deals if you are not already on the cap table. Or they can be large family offices or corporations who like to invest in particular industries but don’t have the skills, connections, resources, or inclination to invest in raw startups. For Pipeline Fillers, you need to understand their investment focus first and then show how your portfolio matches their need. You also want to highlight how they will get access to your portfolio. At DreamIt for instance, we stress the early introductions we make such as invitations to session kickoff events and “LP Day” where our investors get a preview of the newest DreamIt startups well before the general public meets them on Demo Day. We also point out that, as a relatively small fund, DreamIt rarely invests beyond the B round which leaves a lot of pro rata investment rights for later rounds that we can make available to our LPs.

Type: Strategics
Winning strategy: Show portfolio fit

Strategics want to know what disruptive technologies are just over the horizon. They are often corporations who want an opportunity to partner with the best startups before their competition gets to them. They may even want a chance to make some targeted investments and/or acqui-hires. Portfolio fit is critical here. Selling a generalist fund is difficult because only a small share of the startups will be relevant to that particular Strategic but pitching a fintech focused VC fund to a bank or an IoT/smart device fund to a large electronics conglomerate makes a lot of sense. While return does matter, they are largely buying insight so focus your pitch more on your deep industry knowledge and your access to disruptive seed stage startups in that space.

Type: Economic Developers
Winning strategy: Show them the headcount

Sometimes, you may even pitch your fund to the government entities that are first and foremost Economic Developers. Increasingly, the SBIC, states, and even a few of the larger cities have allocated some of their economic development budget to VC investment. This is an entirely different kind of conversation. They want to know how many jobs you will create in their region so be prepared to talk headcount, not returns. Also, there will be strings attached – limits on non-region investments, co-investment requirements, etc. You may even need to set up a side fund for their investment to exclude startups that don’t meet their mandate. Oh, and don’t expect them to move quickly either.

Type: Impactors
Winning strategy: Share their passion

Impactors make up a similar but separate group of potential investors. These may be government entities or non-profits with social goals. Often referred to as double bottom line investors, Impactors want to invest in particular types of ventures such as minority or veteran led businesses or startups targeting environmental or anti-poverty causes. Impactors vary from wanting to maximize profits while constraining their universe of investments to those that meet their mission to those who want to maximize their impact on their primary social metric while at least meeting a minimum target return. Impact investors are typically a poor fit for VC LPs unless your VC fund was constructed specifically with their goal in mind or predominantly targets a closely related industry such as environmental impact investors and a clean tech fund.

Type: Fund of Funds
Winning strategy: Finding them is 80% of the battle

The last category is Fund of Funds. Their value proposition to their LPs is that they can pick the better VC funds, justifying the fees they charge. These fees apply after the underlying VC funds take their fees. There’s been a mini revolt against “Fees on Fees” so these guys are a vanishing breed but if you do meet one, your pitch should be similar to the one you use for Institutionals, only stressing returns instead of capital preservation. Fund of funds may also be looking to slot your fund into their pre-defined set of target buckets so take some time to figure out what their buckets are and show where you fit in. Plus, if your fund doesn’t quite fit cleanly and neatly into their framework, that’s one strike against you. Lastly, because of the fee issue, be prepared for the Fund of Funds investor to ask for a discount of your management fee, carried interest, or both.
So the next time you sit across from a VC and think wistfully about how much nicer it must be to be the one writing the checks, remember this: every few years we go through the same wringer as you do and it’s no picnic for us either!

Acknowledgements: I’d like to thank my colleagues who contributed valuable feedback on earlier drafts of this piece including Skyler Fernandes (Simon Venture Group), David Teten and Katie Bluhm (ff Ventures), Sumeet Shah (Brand Foundry), Amanda Nelson (TCP Ventures), Jorge Torres (VenSeed) and Steve Berg (Antecedent Ventures). In case you are wondering, I’ve opted to list them in the order with which they responded to my request for feedback in the (likely misguided) hope that this will encourage them to answer my emails even more quickly.

Startup founders: How to find the right mentor

Nice piece in TechRepublic about how to find the right mentor:

http://www.techrepublic.com/article/startup-founders-how-to-find-the-right-mentor/

And I’m not just saying that because the author quoted me in it.  :-)

Two additional thoughts that didn’t make it into the final cut:

Advice, Connections, or Credibility? Mentors can bring one or more of these three benefits to the table.  What you need most will direct your search.  Bear in mind that the senior guy at company X who looks awesome on the Team slide may not have time for much more than sharing some vague, but enthusiastic endorsement of your company if asked. Someone more junior may be more likely willing and able to put in the hours it takes to give worthy advice and direction. And while pure corporate types often just don’t understand the ‘startup’ side of the equation enough to advise properly, they can be excellent connectors.

Mentor or Consultant? Don’t mistake the need for expertise with the need for a mentor. Ask yourself this: What will I talk about with this guy in six months? If you come up blank, he’s probably not a mentor.  For instance, if you need to speak to an Information Architecture expert about what tech stack to build on, just pay for a one-time consult outright (or beg a free meeting over lunch) rather than to give away part of your company. Similarly, the master sales / biz dev guru who can get you those critical first customers isn’t really a Connector. You can often compensate him with a percentage of all revenue he generates and (if necessary) a small monthly retainer and save the equity for a true mentor.

Are Accelerators Just Paid Introductions in Disguise?

It was not so much a debate as a “frank exchange”.

I was exchanging emails with the founder of one of the larger startup pitch conferences.  He had asked me if I would promote his event with some of the DreamIt startups who are currently fundraising.  His events are pay-to-pitch and it’s fair to say that, as a general rule, I’m not a fan of that model.

I (politely, I hope) explained my reservations.  I’ve dealt with the issue in more depth here but the gist is that getting in front of key decision makers is a core competence for successful entrepreneurs.  If you can’t get a warm intro to early stage investors who, by and large, are some of the most networked people on earth, how will you get in front of potential customers, distribution partners, etc.?  Paying for access to investors often signals a lack of this core competence, and, more generally, an attitude that something so fundamental to their business should be outsourced.

When I was done explaining, he responded with this deceptively simple question:

“How is presenting at our program different then presenting at your demo day?  Those companies pay you with equity.  Couldn’t you make the point that if they need your services then they are [equally lacking]?”

Respectfully, I disagree.  There is a world of difference between participating in an intense 3 month program where you master key skills vs. simply writing a check.

Putting aside the heavy filtering that is a result of the intense competition for admission into the top accelerators – having seen the numbers first hand, I can confirm that it is statistically easier to get into Harvard than it is to get into DreamIt – that in itself virtually guarantees a better pool of demo day startups than pay-to-pitch presenters, anyone who has been through a top accelerator will attest to how much they have learnt.  In particular, the alumni who graduate from top accelerators leave the program fully capable of networking to investors, clients, partners, etc. Startups who use bankers or other intermediaries leave with some business cards.  It’s the difference between mastering a skill and renting it,  between going to med school or just going to the doctor.

But then again, I might be biased. :-)

What do you think?

9 Things Noah (The Biblical One) Can Teach Entrepreneurs

On Saturday, October 25, Jews around the world (or at least those who actually go to services) heard the story of Noah’s Ark. And so, with apologies to every rabbi who ever tried to teach me anything, here are a few things that Noah can teach entrepreneurs:

  1. Plan ahead. Noah didn’t wait until it started raining.
  2. Be different. The big winners are the ones who zig when everyone else zags.
  3. Go big or go home. Would a row boat have cut it?
  4. When you find the right mentor, listen carefully.
  5. Expect critics. I’m sure Noah’s neighbors had a good laugh at his little hobby. (“Hey funny guys, how long can you tread water?”)
  6. Build a diverse team. That said, you can probably get away with fewer than two of everything.
  7. Speed isn’t everything. In the ark, the cheetahs bunked with the sloths.
  8. Bad times can be good for survivors. Be the low cost producer in a price war, or stay lean when others are splurging and you can be the last man standing in an open field.
  9. Timing matters – don’t miss the boat!

Angel Investing – Fools Rush In Where Family Offices Dare To Tread (1)

Note: This post originally appeared as an article on FOCAPNET.FOCAPNET logo

 

Angel investing is hot… and not just because it’s so cool.

When for over a decade single-digit Venture Capital returns qualify as “top quartile”, seed stage investments have generated 27% ROI. (2)  So it is only natural that family offices and high net worth individuals are eager to get exposure to this sector.  The only problem is, they often don’t have the experience they need to do it right.

Here’s a typical family office startup story:

  1. A family office decides it wants to get into angel investing.
  2. One of the investment professionals goes to a few meetups and generally gets the word out that he is in the market for interesting startups.
  3. He starts getting pitched (directly, via LinkedIn, etc.) by a host of “investment advisors” representing “hot startups”.
  4. A few of these startups look pretty good so the family office invests.
  5. These investments fail miserably.
  6. The family office decides that startups are a “bad investment” and goes back to what it was investing in previously.

Hint: Step 3 is where things ran off the rails.  I’ll get back to that in a moment. 

 

Why family offices are ill-equipped for angel investing

The more sophisticated family offices employ investment professionals who have deep experience analyzing the strategies and returns of public equities, hedge funds, private equity funds, etc.  These are all well defined instruments, within generally limited investment universes, for which substantial data is available.  Even if you are considering seeding a hedge fund or committing to a newly minted PE/VC fund, you can still mine the principles’ track for a fair number of data points.  Furthermore, there are well-established channels for learning about new opportunities (e.g., “capital introduction” dinners) in these spaces.

Now reverse every single one of the above characteristics and you get angel investing.  Every halfway decent startup opportunity is unique, solving unmet needs in different industries – sometimes in industries that don’t even yet exist.  There are no registries or directories of startups, no associations to join.  And you can forget about data entirely with a pre-revenue company.  At best the founders have one or two reasonably successful prior ventures under their belts. (If they had a real home run under their belts, they wouldn’t need investors at all.)  Furthermore, the best way to find great startups to invest in is to know other great startups so if you aren’t already deep in that community, you’re already disadvantaged.

Unfortunately, most family offices don’t realize how fundamentally different early stage investing is from other alternative asset investments.  So they don’t see anything amiss when investment adviser brings them startups to invest in. (I told you I’d get back to step 3.)  They are used to meeting emerging hedge fund managers that way so why shouldn’t they find a great startup that way too?  Because the best startups are never, ever represented by an investment advisor.

Think about it.  VCs are the most networked people on the face of the earth.  VC present at panels or judge pitch events practically every week.  They meet dozens of entrepreneurs every week and know – and have often co-invested with – virtually every other VC in our area.  If a startup founder can’t network his way into a warm introduction to a VC or angel, how is he going to find customers or key strategic partners?  Is this advisor going to be holding his hand then too, after your check has cleared?  Plus, the very fact that the founder thinks he can waive his hand and simply have someone else take something this crucial to his business for him is huge red flag in and of itself.  So any startup that has an investment advisor fundraising for them is already automatically suspect.  In practice, the deals the family offices are being shown by these advisors are the hairy, old, over-shopped deals that every VC and halfway serious angel have already turned down.  It’s no wonder they fail miserably.

To be fair, to the untrained eye they don’t look that bad.  Perhaps they have a cool piece of ad tech that you are convinced will take agencies by storm.  You have to really know the industry to understand why agencies turned them down two years ago when they first tried shopping their solution around.  That fantastic social media marketing tool?  It’s so wonderful that five other companies are already doing it and they are all making better progress than the one you were pitched.  But if you aren’t seeing dozens of startups each month, there’s no way you could be expected to be on top of all these trends.

 

So what’s a family office to do? 

In theory, a family office could hire a seasoned angel investor to invest on their behalf.  But good luck finding one.  Many angels are running their own businesses and/or are entrepreneurs who had a large exit and have no interest in working for a family office.  Also, angel investing is a numbers game.  Most startups will fail, and many of the rest will be modest successes.  You have to invest in many, many startups to have a reasonable chance of 1 or 2 of your investments being a home run.  There’s a reason Dave McClure named his fund (now an accelerator as well) “500 Startups.”

Fortunately, there’s a better option:  Startup Accelerators.

Accelerators(3) are the boot camps of the startup ecosystem.  Companies accepted into top accelerators are the very best, earliest stage startups in the world.  The top accelerators typically get hundreds of applicants for just 10-15 spots.  Having just run the screening process for DreamIt NY’s summer 2014 program I can personally attest that this is no exaggeration.  The odds of getting into Harvard are slightly better than getting accepted into DreamIt.

Accelerators give the startups they accept a little cash ($20k-$40K on average), co-working space for the duration of the program (typically 3-4 months), and extensive mentoring, coaching, and introductions.  Finally, on “Demo Day” the startups graduate by pitching their business to an audience of hundreds of active angel investors hand-picked by their accelerator.  In exchange for all this, the accelerator gets equity in the startup (usually 6-8%) and the right to co-invest in the startup’s seed round.

From the perspective of the family office, accelerators can be the capital introduction dinners for startups.  Unlike the shady investment advisors discussed above, accelerators are personally invested in the startups they accept.  Accelerators do not get commissions on the fund they help their startups raise; they only profit when their portfolio companies have an exit so their incentives are aligned with the other angel investors.

But they are more than just a trusted recommendation from a fellow angel investor.  Accelerators like 500 Startups, DreamIt, TechStars, and Y Combinator invest in dozens of startups each year and can bring a structure and rigor to the investment process that few angel investors have.  Established accelerators bring unparalleled networks and reputation to the table enabling them to source the very best new companies out there.

Many accelerators are structured much like VC funds.  But there is one crucial difference: co-investment.  Even the most co-investment friendly VCs only make their portfolio investments available to LPs if they are unable or unwilling to invest their full pro rata.  If it’s a great portfolio company, the VC will continue to invest until it runs out of powder or starts bumping up against position caps.  And if the VC is able to but does not want to exercise its full pro rata, do you really want a bigger stake in that company?  In both cases, the VC eats first and the LPs get leftovers.

Accelerators on the other hand, rarely invest in more than a small fraction of the portfolio company’s seed round.  As I mentioned above, early stage investing is a numbers game so they reserve most of their investment capacity for new startups.  As a result, 75% or more of the round goes to new investors.

Think about that for a moment.  Here’s an entity that filters out 98% of the startups they see, takes the top 2% and gives them all the help a young company could ask for, and then willingly steps aside and lets any other angel or VC swoop in and invest in those elite new ventures.  No commissions, no membership fees.  Wow.

If all a family office did was go to the Demo Days of the top 4 or 5 accelerators and invest in the presenting startups, the filtering effect alone would give them a high quality portfolio of early stage investments, no additional effort required.

For the family offices who want to build their own experience base and startup network, there is an even better option: invest directly in the accelerator.  Accelerators typically give their LPs early access to their new class so LPs can track a startup’s progress over a longer period of time before deciding to invest and/or can invest before Demo Day and avoid the risk of missing out on the hottest prospects.  Furthermore, most accelerators will gladly explain their selection process, describe how they are assisting the startups, and introduce LPs to other members of the startup community.  This practical education is not something you can buy anywhere but you can get it for free simply by investing in something you already want to invest in.

Investing directly in a top accelerator also makes sense from an efficiency perspective.  Even investing the bare minimum $25K per startup (and some startups insist on $50K or $100K minimums), creating a portfolio of 100-200 startups would cost a family office $2.5M-$5M.  But this leaves no money for follow on investments.  As a rule of thumb, you want to set aside $1 for follow on investments for every $1 initially invested so getting that 100-200 startup portfolio actually means committing $5M-$10M to early stage investing.  In contrast, you could invest $1M (4) into the accelerator’s fund for the same portfolio of 100-200 startups, including follow on investments.  That comes out to just $5K-$10K per portfolio company.

So let’s re-write the family office story:

  1. A family office decides it wants to get into angel investing.
  2. It researches the accelerators in its area and invests in 1 or 2 of them.
  3. It spends the first few accelerator cycles learning the ropes and making connections.
  4. As it gains confidence, the family office invests directly in a few of the accelerated startups, effectively doubling-down on a few, high conviction plays.
  5. The diversified portfolio does well
  6. The family office makes disciplined, intelligent, efficient angel investing a formal part of its allocation strategy

Now how’s that for a happy ending?

 

(1) Just in case you were wondering, “For fools rush in where angels fear to tread” was first written by Alexander Pope in his poem An Essay on Criticism.

 (2) Right Side Capital analysis of eight large studies of historical angel investing returns in the US & UK (http://rightsidecapital.com/assets/documents/HistoricalAngelReturn.pdf

 (3) Sometimes called incubators, although incubators are more often shared co-working spaces with some additional services that are of value to startups.  Unlike accelerators who rigorously screen their applicants, incubators are generally open to all, space permitting, as long as they can pay the rent.

 (4) Many accelerators will allow family offices to invest as “individuals” rather than “institutions” enabling them to qualify for minimum investments of $500K or even as low as $250K, which comes out to as little as $1,250 per startup(!) 

100% of Nothing

“We are just not sure it’s worth 6% of our company.”

Accepting the position of Managing Director in charge of DreamIt’s NY startup accelerator meant a lot of things, two of which include:

  1. Meeting a lot of really, really interesting startups  :-)
  2. Far less time for blogging  :-(

One recent experience cut right to the core of the accelerator experience and has been bothering me so much that I’m going to share it despite having far more pressing items to handle in the one week I have left before DreamIt NY Summer 2014 kicks off.

We receive hundreds upon hundreds of applications for the summer accelerator cycle and meet with (in person or via Skype) over 50 of them before winnowing them do to the 10-15 companies we accept into this program.  Despite the long odds – you are actually statistically more likely to get into Harvard than DreamIt! – you may be surprised to hear that not every company we extend an offer to ultimately accepts.  Most of the (small) handful of companies who decline do so because they want a few more months to work on their business before entering our program.  As DreamIt has accelerator programs every few months, our philosophy in these cases is generally, “We liked you now, we’ll love you even more after 3 months of further progress.”  So if I’m sad not to have them in DreamIt NY Summer 2014, my colleague Patrick FitzGerald will be thrilled to have them in DreamIt Philly Fall 2014.

One of the startups we accepted, opted to go into a different accelerator program.  We ‘win’ far more than we ‘lose’ but I won’t pretend this doesn’t happen from time to time.  I think they made a mistake, especially given the nature of their business and the industry they are in, but the other accelerator runs a good program as well.  So now I know how Harvard feels when a student they accepted goes to Yale instead.  This isn’t the situation that bothers me.

One startup we accepted signed the offer letter and we both began making plans for the summer.  Then I get a call from the founder to say she was having second thoughts.  Would we be able to find the right mentors for her startup?  Could we make useful industry connections?  By the end of the call she stated that her team felt that they would rather just continue working out of her parents’ basement than give up 6% of their company to an accelerator.

Let’s ignore the fact that these were all questions that should have been asked before signing our offer letter – ideally even before applying to an accelerator program – and focus on the core complaint: is an accelerator program worth 6% of our company?  For the answer to be Yes, a very simple equation has to hold true:

EV(startup+accelerator)*94% > EV(startup)*100%

In other words, is the Expected Value of 94% of your startup with the accelerator’s help worth more than the Expected Value of 100% of your startup without any help?

So how do we think about the Expected Value of a startup?  Let’s simply the problem with some hypothetical numbers.  Let’s assume that a “success” means that your startup sells for $100M and that the “odds” of success are 1:100 or 1% (note: I’m a huge fan of making the math easy).  In this case:

Expected Value = $100M * 1% = $1M

(hmm… I wonder if this is why so many priced seed rounds are at a $1M pre?)

So for the accelerator to be at least as good a deal as going it alone, the odds of success have to be high enough to get you to a $1M+ Expected Value despite giving up 6%.  Let’s whip out the calculator and solve for x:

94% * $100M * x% = $1M

x% = 1.064%

So, whether they understood this or not, what this startup was saying is, “We think your accelerator cannot increase our odds of success by even 7 one-hundredths of a percent.”  Wow.

Now there are a lot of new accelerators out there and I firmly believe that some (many?) of the newer ones with no track record of nurturing successful startups, no real network of experienced, well-connected mentors, no built-in audience of hundreds of active angel investors – these accelerators probably cannot move the needle when it comes to increasing a startup’s odds of success.  In fact, entering into a poorly regarded accelerator may even reduce the odds of success due to the negative signal.  But to think this about an accelerator with a six year history in five cities where over one third of our ‘graduates’ have collectively raised over $115M and who are now worth in aggregate over $410M, that’s mind boggling.

Now I like these entrepreneurs and I honestly and truly hope they succeed despite this decision but I fear that they have just made a horrible mistake.

Thanks for letting me get that off my chest.  Now back to work!

 

 

Two must-have, time-saving, super-easy productivity tools: Evercontact & Boomerang

I love these two services so much, I’ve not only paid for them, I have even added them to my email signature.

Why? Since this post is about time-saving productivity tools, I’ll be brief.

Evercontact (http://bit.ly/LDNVL5)Image
I used to spend a lot of time copying and pasting names, phone numbers, emails, addresses, etc. out of emails I’d received into my Address book.  Evercontact (formerly WriteThat.Name) changed all that.  It automatically scans incoming email, identifies signature blocks, and imports the data, creating new contacts and updating existing contacts.  There’s a fully automatic mode where this happens entirely behind the scenes and a manual mode where they periodically alert you about new contact information that you can opt to save or ignore.  There’s even a feature where they will retroactively scan your past year of email to extract the contact data there.  It doesn’t get any easier than that.
Special shout out to Brad Patterson, the face of evercontact.  Hit reply to any email you get from evercontact and he actually responds, often within hours.

(Yes, I am aware of CardMunch but that app is inexplicably still not available for Android.  Plus, I get fewer and fewer business cards these days.  I still get some, though, so I’m looking into CamCard for that.  Stay tuned!)

I had heard about this service long ago but hadn’t got around to trying it until recently and I’m kicking myself for all the time I could have saved.  I send a lot email where it’s on me to make sure there is follow up (e.g., intro requests email, bizdev proposal, etc.).  I used to send the email and then manually add a reminder to my calendar.  Boomerang plugs into my Gmail account and adds a 2nd row of options to the Send Email screen:
Image
I simply check the box, decide how long I want to wait, and hit Send.  If there’s no reply in that time period, Boomerang automatically sends the email back into my Inbox.  So much less effort and my calendar is so much less cluttered.
I don’t use the Send Later feature that often but it is sometimes useful when I’m working over a weekend but don’t want my email to get lost in the Monday morning email flood.  You can (and I used to) simply save an email to Drafts and manually send it later but this is one less thing to remember.
While Boomerang’s Gmail plug-in works wonderfully, my one disappointment is their app.  The Boomerang features are not (cannot be?) added to the Gmail app so if you want to use these features while on the go, you need to install the Boomerang app.  I like the swipe-left-for-additional-options interface (right swiping an email will archive it, just as on the Gmail app) but the Boomerang app appears to show me all my emails, not just the ones in my Inbox or Priority Inbox.  Also, Boomerang doesn’t update as quickly as the Gmail app and occasionally fails to connect at all.  If they could replicate my Priority Inbox view in their app and fixed the updating issues, I’d probably make the Boomerang app my primary way of checking Gmail on my phone.
If you try these service, let me know what you think.  And of course, if you have other great productivity hacks that you think I should know about, I’m all ears.
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