Interview with Start-Up Chile Mentor Brendan Baker


Brendan Baker is a Startup Chile Mentor and expert on fundraising and pitching for young tech companies. He has researched seed round fundraising, managed the dealflow at AngelList through more pitches than we could count, and seen some of the best pitches in Silicon Valley from the inside at Greylock. In addition to Startup Chile, he also works with accelerators like AngelPad, 500Startups, and


We wanted to ask Brendan about a pitching, fundraising, and building early stage companies. Our interview with him is below.


Startup Chile: Brendan, thanks for joining us.


Brendan: My pleasure. Thanks for having me.


Let’s dive in. You’ve seen a lot of startup pitches. What are some of the weakest parts of a pitch you commonly see?


A few years ago, I would have said the traction sections. People didn’t really know what it meant, or how to showcase their progress. But now there are lots of resources explaining how to frame traction, and accelerators have coached this to a fine art. Almost too well.


There’s a lot of resources out there on what slides you’ll want to consider, and what might go in them. Market, competition, team, problem, solution, product, business model, and so on. That’s all out there, and most entrepreneurs do that reasonably well. The bigger weaknesses are big picture things.


Interesting. What big picture things do entrepreneurs often get wrong when pitching investors?


Well the first point is that they generally try to jam far too much into their deck. Cut slides that don’t add anything. Cut bullet points from slides (3, maybe 4 max please!), and cut words from bullet points. A good starting point of reference is 10-15 slides for a one hour meeting. You can stretch that to 20 or 25 if you really need to, but keep it as short as possible.


Think of it this way: there’s maybe 3 things in your pitch that are truly memorable, truly exciting for an investor. If those 3 things are buried in the 4th bullet point of the 38th slide, an investor’s going to be asleep before she even hears about it. So leave in only what is truly essential.


A second thing is that they spend far too much effort trying to be credible, and to be able to defend every part of their business. A little of that is important, of course. There can’t be huge gaps in the story. But after a minimum, switch your efforts to figuring out what makes you truly memorable. Often there’s only two or three things that matter here. Make those as clear and obvious as you can.


And then the last thing entrepreneurs often miss is they don’t convincingly describe why high level trends are adding fuel to their company’s direction. Try to answer this question: “why is now the only time that this specific company could be built?” That will help you identify the important social, technological, or political trends that are opening up opportunity for your company.


That seems a little fuzzy. Specifically, how can entrepreneurs do this?


It’s true, it’s a little fuzzy, and there’s often no right answer. But there are some techniques to improve.


To identify which high level trends matter, I’d try to answer this question:


“Now is the only time our company could be built because _____________ is changing, and opening up opportunities in ____________. The companies that have existed before can’t do it, because _____________.”


Try to do that 10 different ways for your business, and then pick the best 2-3 examples. That’s a good place to start.


To draw out what makes your company memorable, try this. Do your practice pitch for 5 people. Choose people who know how investors think. As you do it, ssk them to make a note any time they hear something that excites them, or anything that causes hesitation for them. After a few of these, you’ll be able to see patterns. Make sure the few exciting (i.e. memorable) things are very, very clear in your pitch.


And finally, to clean the junk out of your presentation, go through a checklist:

  • Do I have more than 15 slides? If I had to cut out 3 slides, what would they be?
  • Are my slide titles clear, short, persuasive, and formatted consistently?
  • Do I have more than 4 bullet points on any slide? Are the bullet points the same format on all slides?
  • Can I cut 25% of the words for each bullet point in my slides?
  • Can I remove any images that don’t add to the presentation, like clip art, background images, and so on?


Anyways, go through this list after each draft of the presentation, and you’ll get it to a good place over time.


Let’s shift gears. We have a lot of companies that may want to raise investment in another country. Is that possible?


This is a great question. The answer is yes, and it’s easier than before, but it’s still much harder than entrepreneurs often think. You can’t walk into a new country and expect to raise money in a couple weeks.


You need to build your early network before pitching. Sometimes this means traveling there a few times before you go there to pitch, to start to meet people. Sometimes you can fundraise on your first trip, but you really do need to arrive a month or two early, as it takes awhile to build relationships. And of course, figure out who in your current network can link you to people there.


It’ll help a lot if you actually plan to have a presence in the place you’re trying to raise money. In that case, investors will be much more receptive. Will it be a main market for you? Will you be opening up an office there? Moving your main office there? If any of this is the case, it’s good to share that with investors.


And lastly, you should know that investors in different geographies will have different levels of sophistication, and want to hear different things. For example, in Silicon Valley investors don’t often want to hear about basic trends like ‘mobile is increasing’ as everyone knows that, and don’t care about financial projections at the earliest stages, as nobody believes them. This may not be the case in other places. Best to ask a few people who know how where you’re going to pitch is different than where you’ve done so before.


Finally, get your presence on AngelList fired up. It’s great for researching investors in new locations, and having a convincing presence.



When you’re pitching, what types of investors should you be looking for?


Let’s assume that you’re pretty early – seed stage, and trying to raise under $1M USD.


The thing companies like this often try to do, which is often counterproductive, is pitch the big obvious venture capital firms first. Instead, look for angel investors. Angels used to be hard to find, but with AngelList, Crunchbase, and Google, you should be able to easily build a list of say 50 or 100 angels in a place like Silicon Valley. After angels, you can add seed funds like 500 Startups, but I’d still pitch a bunch of angels first. And if you end up in front of a few larger VCs too, that’s fine. But don’t start with them.


Are there any new approaches or tools that startups should be using to raise money as they do this?


Absolutely. In many places, it makes sense to use AngelList. It can be a tremendously effective way to raise money, complementing traditional processes. If you’re in the UK, I’ve heard good things about Seedrs. There are some others, but I think those are the leaders right now.


If you’re building something physical, you’d want to seriously consider using Kickstarter, Indiegogo, or a similar crowdfunding platform. Now, the network effects aren’t quite as strong on these as with AngelList, so it’s a little less important to choose the biggest one. Pick the one that works for you. But many, many startups are either using this for their first capital, or using it for early demand sensing and marketing even if they’ve already raised money (and sometimes millions of dollars too). The crowdfunding ecosystem is still young, and so you’ll have to do a lot of the work yourself. Fundable has a decent list of tools that can help with parts of this and new companies like Pitchtop may help in the future.


You did some interesting research at Oxford. What did you learn?


The project looked at all the people an American entrepreneur met to raise $1M from 14 investors. You can see it here.


There were a few things that surprised us. First, is just that it takes a large number of pitches to raise money. Daniel met over 130 investors. Many first-time entrepreneurs think they can just know a few investors and raise money. They can’t. It’s a numbers game, and you have to put in the work.


The flip side of that, is that when you’re in the middle of this process and have been rejected a bunch of times, that’s normal. If you’re converting 10% or more of your pitches to investment, you’re doing fine. It’s important to realized that, and not feel like crap.


And the biggest thing the study taught us is how much momentum plays a part as you find your way through investor networks to the right people. It’s a little hard to see without looking at the material, but you want to kind of track who is making your introductions to investors, and who of those investors is making introductions to other ones. When that’s working as a collection of behavior, you need to pay attention, and invest in that part of the network. As I said, a little hard to describe, but it really reinforced how not all connections are created equal.