The New Year's Pentathlon runs from January 6th to January 21st. It's the 6th Pentathlon we've held, and each one gets rave reviews. (Check the page for many testimonials.) It's a great way to start 2018 off with a bang and have two weeks of peak performance to start the year, as well as take lessons and skills forward with you all year.
For Cyber Monday only, when you get your spot on the Pentathlon, you get a +1 to give to whoever you'd like: a friend, family member, coworker, or colleague. The Pentathlon works great when you do it alongside someone you know and care about — we've had cofounders come together, husband/wife teams come together, we've had brothers do it together and connect more through it... it's pretty great.
Also potentially a great holiday gift. Normal price is $300, so it's a snazzy thing to be given. (You can inquire in advance if the person is available from Jan 6-21.)
if you're curious, check out —
Salut, hope to see you on the Pentathlon,
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We're doing the Ultraworking Pentathlon again, from 7 January to 22 January.
The first Pentathlon was a really big success. We've incorporated feedback and the next one is going to even better.
The Big Idea
The big idea is very simple: there's hundreds of "known best practices" and 1% edges in the world that most people aren't doing them. There's also dozens to hundreds of little techniques, tricks, and advantages you can stack up to make your life run better.
I just sat down with Shai Goldman, a Director at Silicon Valley Bank. My interview with Shai is the second in a series of interviews I'm doing to help entrepreneurs raise funds in the Valley. (The first one was with Naval Ravikant of AngelList) As someone who's new to the valley myself, I've found the experience to be interesting, engaging and yet complicated in very subtle ways. I'm hoping to help others who have the will and desire navigate Valley politics and culture more quickly and effectively through these blog posts. Consider it a "pulling back of the curtain" so to speak, to the extent I'm able to do so.
Having a chance to capture some content with Shai was great - he has been a phenomenal resource for us. We were lucky to have chosen Silicon Valley Bank as our bank (on the recommendation of our lawyer, Mike Lincoln of Cooley Godward), so we had a pre-existing relationship with SVB. That came in handy when we opened our San Francisco office of AppMakr and I was able to contact Shai through the existing SVB relationship.
Although Shai hasn't announced this to many people yet, he'll be moving to NYC in January for a while, so if you're looking to get connected, you only have a few months left to do so!
Here's the video:
I just sat down with Shai Goldman, a Director at Silicon Valley Bank. My interview with Shai is the second in a series of interviews I'm doing to help entrepreneurs raise funds in the Valley. (The first one was with Naval Ravikant of AngelList) As someone who's new to the valley myself, I've found the experience to be interesting, engaging and yet complicated in very subtle ways. I'm hoping to help others who have the will and desire navigate Valley politics and culture more quickly and effectively through these blog posts. Consider it a "pulling back of the curtain" so to speak, to the extent I'm able to do so. Having a chance to capture some content with Shai was great - he has been a phenomenal resource for us. We were lucky to have chosen Silicon Valley Bank as our bank (on the recommendation of our lawyer, Mike Lincoln of Cooley Godward), so we had a pre-existing relationship with SVB. That came in handy when we opened our San Francisco office of AppMakr and I was able to contact Shai through the existing SVB relationship. Although Shai hasn't announced this to many people yet, he'll be moving to NYC in January for a while, so if you're looking to get connected, you only have a few months left to do so! Here's the video: Here's a transcript of the video: (learn how & why I do this) Shai Goldman of Silicon Valley Bank re: Entrepreneurism in the Valley Daniel- I am here with Shai Goldman of Silicon Valley Bank, who is awesome by the way. You've been a real asset to our company and we are much appreciative and glad to be a Silicon Valley Bank clients. Can you just tell us a little bit about what you do at SVB. It seems like you've got a pretty awesome role there. Shai- Yeah, I probably have one of the better jobs in the community. Essentially part of my job is to create a community of entrepreneurs and to really foster that community. We are a commercial bank so we are providing banking services for start-ups, what we are trying to do is create a community around that and try to add value along the way. Some of the value that we do is connect start-ups to investors and also bring other like minded start-ups together to share war stories and talk about the challenges about their particular sector. We do a lot of those things, we also do match making and also events just for start-ups. Some of those things are educational and it's really just a free value at a service and we feel that if you give back to the community that they will stick with us for the long run. We really want to establish long term relationships with start-ups. I cover the anything essentially anything web based- mobile, consumer Internet, gaming, digital media, software as a service- as long as the start-up is in that sector, I try and help them with all the things that I have mentioned. I have colleagues that cover the other sectors clean tech, life science, hard ware infrastructure and enterprise software. Daniel- So your job is basically to know everybody in Silicon Valley? Shai- Yes, I go to a lot of the conferences and events. To an extent I am the face of the organization at the early stage the at the pre-venture back stage. The goal is that people know who I am and that I represent SVB and if they have anything they can get a hold of me. Daniel- That's cool. You put on a lot of events, you are doing something in a couple of weeks, a panel. I know you just did a panel the other day. Are these for knowledge transfer and learning or what goals do you have when you do these things? Shai- It's a combination of things. We will do 25 events in the bay area just for start-ups. It's all free so there is no charge. It's a mix of things, we will do pitch events where start-ups can present to VC's. We just had one of those last week, we had 40 companies presenting to about 140 VC's. Daniel- Do those pitch events actually work? Let's just be completely honest here. Do the VC's who go are they actively investing? We didn't do any pitch events, the only similar thing that we did was AngelList which I think is different. What do you think about the pitch events? Shai- There are a few different variations of pitch events. The goal of our event is to get start-ups to meet 3 or 4 quality investors that they didn't know before. That is the goal, it's hard to say you are going to pitch at this event and you will get funding. What I will say is- there are quality entrepreneurs in the room, there will be quality VC's in the room and that we hope that something happens out of that. The goal is for the VC's if they can meet 1 or 2 quality companies. If the entrepreneur can meet 3 or 4 quality VC's then those are a success for us. We have had clients close on funding from that event. I wouldn't say that it is a very high % but I would say that its maybe 5% of the companies who have presented and met their VC at the table. Daniel- It's like an awareness. Shai- Yes, and we also have a lot of clients from across the country that come to the Bay Area that do not have access to Bay Area VC's. If you are a Bay Area start-up you will have easier access to Bay Area VC's. If you are from Seattle, Philly or Boston etc they may not be as successful out there but if you come here and meet those VC's, that is a good win win for them. Also, a lot of things happen if you meet a VC and they like what you are doing, they may pass on that company but say hey I have three other VC buddies who I think this will be a fit. So they are actually helping to make other introductions, it's almost like a multiplier effect. That actually happens, sometimes it is hard to track because the company may not be pitching for money right now, they are pitching for money 6-9 months down the road. Daniel- Do they pitch at these events, even though they are not actively looking for funding at that moment? Shai- Yes. There is a lot of blog posting around this sort of you want to create a relationship with a VC before you are out there pitching. You want to start building that relationship and build that trust. You also want to show that you can hit some milestones that you say you are going to. They get to know you along the way. That happens a lot of times, you don't want to do that with too many investors but you can cherry pick 4 or 5 folks that you want to maintain those relationships. Once you are ready the VC is up to speed, the trust is already established and they are ready to pull the trigger. People use the dating analogy and a sort of that is true. Maybe not at much so on those seed stage, if you raise money through AngelList or maybe a smaller round it comes together pretty quickly. At least I have found. Daniel- What is pretty quickly, days, weeks, months? Shai- If you can close on funding from the time you pitch your first VC or Angel investor until the money is in the bank, the whole round is in the bank, legal docs and everything, I think 3 months is pretty quick. You don't see that very often. Especially if you are raising a smaller seed round, we have a lot of investors who are trying to corral other folks, different buyers and if you do prefer notes its easier and its less legal documentation. If its a full blown round it is a lot more process. Daniel- What do you think about convertible note verses A rounds, actual equity rounds, do you have any thoughts? There seems like there is a lot of talk about the pros and cons of those. Do you see companies doing one or the other and do you think they shouldn't be doing that and doing something else? Shai- Personally or as an organization for us it doesn't really matter if its convertible notes or a price round. Because we are looking to broaden the banking services so it doesn't really change that prospective. The trend that I am seeing on the seed stage or that million dollar round the majority are convertible notes. It all depends on what sort of investor you are going after. the larger VC funds that are 200million and larger, from what I have seen from our clients those are usually prices rounds. Sometimes you get more of the hybrid you get a larger VC to do 500k and then it is augmented by Angels. That can be a convertible note. It seems to me that on many occasions the entrepreneur decides which direction they want to go and which way they are more comfortable with. If they say I am going to do a convertible note, its either you like it or you don't. It depends on how much leverage you have it depend on how hot the deal is sometimes you cant make that call as an entrepreneur. You see all the blog post that say oh the round came together in 3 days and we decided the evaluation and we decided who is in and who's out. That's not the norm, most rounds don't come together like that. The blog posts say that and entrepreneurs see them and think a round came together quickly it sets the wrong expectation for them. If you look at the average entrepreneur that is not the process. It is much more complicated, its a much longer process, its not that easy most of the time. Daniel- It was a very eye opening experience for us the first time out here in the Valley and it took us 14 weeks, about 3 months. Shai- And that's good because you are a company that was coming from out of town. If you are an established entrepreneur and you are part of the circuit and you have these circles of entrepreneurs, different sectors, it's almost clubby, cliquish as well. That definitely happens in the Valley. When you come from out of town and no one knows who you are really its much more challenging to raise a round. For you to come from out of town and you guys were more established you had more revenue and more traction which is good. Typically its much more complicated and a lot harder process to come here, get established, create your own brand and then raise that round of financing. Daniel- Lets talk about that for a second because you were nice enough to meet with me when I was first here in town. I think that was a big reason of why we were able to get into those circles and get to know those people. What do you recommend for companies that aren't in the Bay Area but are thinking of coming. Should they contact you, get an account with SVB, are there other people like you that people who don't know anyone should come and meet? Do you usually meet with companies that you don't know? What should someone do who is new to The Valley? Shai- I think it depends on what sector you are in. There are small circles of entrepreneurs and VC's that depend on what sector you are in. They all sort of get to know each other so depending on what sub-sect you are in you have to figure out who that small circle of people is in the Bay Area. Try and break into that circle somehow. You have a lot of those facilities like the one we are in today SOMACentral. This is a great place to get plugged in to other entrepreneurs. I am sure plenty of VC's come up here and hang out because you have quality companies. You have Dogpatch and Kicklabs, NextSpace you have a bunch of co-working places where entrepreneurs can meet other folks and get plugged in pretty quickly. Especially in San Francisco, the whole SOMA area has so much activity in it. I always suggest for entrepreneurs that come from out of town and they are in the consumer Internet mobile digital media space even SASS companies to come into to SF hang out in SOMA. You can meet tons of people that way. I think the co-working facilities are a great way way to go. Then you have just a plug for one our clients- Start-up Digest, you get a lot of traction. There are so many events that take place in the Bay Area that make it every unique. Every night are 4 or 5 events that you can go to. If you are an entrepreneur and you only events, it can be over whelming. You think well which one do I go to, do I go to the crappy ones or the high quality ones. I think guys that started Digest help you weave through that list of all the events. I think as an entrepreneur you should be going to events every night of the week. I think it is good to be plugged in but you also want to be working doing your coding, building your product, hiring that sort of thing. Sometimes you hear of these guys that are going to every event out there and some investors might be thinking well why are these guys at every event, doesn't he have stuff to do? You sort of have to be careful around that, pick and choose what events. Your time is valuable. Of course at SVB we do a lot of of our own events we are pointing to that eco-system so if you try to connect to certain investors or certain entrepreneurs we can probably help out with some introductions and get you situated. We can let you know who the good core facilities, here are the events that I go to that I think are a good fit, here's our events that you can check out for free. I think its some what easy to get plugged in to the Bay Area as long as you make a concentrated effort to do that and to ask people. I think people in the Bay Area are really friendly its true. Not in other geographies but here I think most entrepreneurs are really friendly and they want to help you , make sure you succeed and will open doors for you. Daniel- Speaking of that, you see a lot of start-ups in all stages from the very beginning I can imagine through funding. What are some things that you see start-ups not doing well, what kind of mistakes do you see them making? Are there trends, things that you wish that start-ups would do differently to make it more successful. Shai- Some of these are more simplistic. Put them together a pitch deck or how to fund raise. If you are a first timer you don't really know what the processes of fund raising are. There are a lot of blog posts around it so you can get a little more educated. Actually once you are going though that process yourself it's a lot different than reading a blog post. Figuring out the fund raising process is challenging because there are some investors that will take meetings but are not actively investing. Part of what I try to do for my clients is tell them the investors that I know are active and that are a fit for them. Let them know they should prioritize those investors. Create that tiered approach of which folks to go to first, you can actually narrow down the fund raising process by knowing who is actively investing in your sector and your stage. I see a lot of investors that just take meetings with anyone and entrepreneurs taking meetings with investors that aren't really fit. Then you are just spinning your wheels because you spend in hour in the meeting, prep time, drive time you are basically spending 3 hours in one meeting. Then you have all the follow up stuff. I think the fund raising process can be more simplified by just talking to different resources around there. Also, a lot of folks go out and try and raise a round too early so they are not really ready. You have to gauge and talk to people, other entrepreneurs and maybe service providers who know know what VC's are looking for. If you are raising that 1M dollar round of financing, you've got to be at certain milestones. I see some entrepreneurs go out to market too early. Thinking of yeah I can raise 1M dollars, then spend three months trying to pitch and then they figure out they are too early. I then I have told them that I thought they were too early, you should probably get a few more milestones so you have to gauge where you are as a company. Daniel- It also seems that it has a lot to do with who you if you've done if you've had an exit before, then it seems like investors would be much more likely to believe in you the person with an idea versus having to show traction. Shai- If you have a good background a sort of pedigree it's not even a necessary exit or other start-ups you've worked on but it's if you're at Google, Facebook or Twitter and you are a certain level than that has to cloud around that. It's a mix of that and also what start-ups you've worked on but sometimes you have a lot of first time entrepreneurs who raise the majority of rounds financing there at a seed stage, there first time entrepreneurs. It's not like they have a huge track record but they get to know who you are and whether you're credible and people are always judging you. Anytime you're meeting with an investor or even another entrepreneur or they don't really know you in the first 30 seconds they start judging, ok is this guy legit, should I spend more time with him. Daniel- It does seem like it happens in the first like you are saying in the first 30 seconds that I've heard of investors say that they know within the first minute whether they are going to invest in the deal or not. Shai- Yes, part of it is just your presence. It's your presence, your personality.... Daniel- So what should an entrepreneur do to have a better presence? Is it self confidence, is it being passionate? Shai- I think its a combination of those two things. Having that self confidence and being passionate. I go through a lot of pitches with entrepreneurs just coaching them and giving them feedback about you should change this slide or you want to maybe not say those certain things. Some entrepreneurs I meet with are just not passionate, if you are working on this start-up everyday, every minute of your life, you should be pretty excited about it. You should be leading forward in the meeting and be really passionate, maybe standing up going to the white board and sometimes I don't see that. Also, people have different personalities, maybe its geared more towards engineers but some engineers are not really out going. Maybe not just the engineers but some folks are more technical and maybe not the most outgoing. For the CEO you have to get over that, part of just going to events and getting comfortable with who you are, getting comfortable talking to people and just being out there. Some people have it and some people don't but I think you can work on it even though you may not be the most personable person. I think you can be calm and still have a good presence and you can come off as really educated and an expert in that particular field. Some folks just lack that sort of confidence and its critical. Daniel- So work on putting yourself out there, speaking in front of others, being passionate about what you do. Shai- When I started at SVB, I was right out of college, I was 22 years old. I started consciously going to mixer events. I was outgoing to a certain extent but I wasn't outgoing in those sort of situations. I just forced myself to go to a lot of different events and just getting more comfortable talking to people, saying the right things and gaging if someone was interested in what you're talking about or just moving onto the next conversation. I even did Toast Masters, I hate public speaking. Daniel- Would you recommend Toast Masters? Shai- Yes, I thought it was great. Now I feel a lot more confident in doing public speaking, it's not just talking in front of a room of 200 people it could be 5 people. If you're pitching to a VC it could be a partnership and if you don't have the confidence level and you're not projecting appropriately. It just makes you look bad. You gotta work on that if you are self conscience and you don't have the skills you can build those skills. Daniel- I've also been involved in Toast Masters in the past, not out here though. I assume there are some great Toast Masters groups out here in the Valley. Shai- There are everywhere. You have to find the one that is sort of a fit for you because they have different personalities some are more sector focused. There are different geographies, I thought it was a good resource. Daniel- So for anybody who hasn't been to Toast Masters it's a public speaking organization where you can practice public speaking. Shai- Yep. Daniel- What are some of your favorite blogs? You've mentioned blogs a bunch of times , do you have ones that you read on a regular basis? Shai- I do yes, Mark Susters Both Sides of The Table, I read that frequently. I thought he has some really good posts. Dave McClure he posts not as frequently but he has some interesting things. Daniel- Some fiery ones when he does. Shai- It's entertaining but they are also some good points there. Brad Felt and Fred Wilson, and then some of the regular media ones like Tech Crunch, Venture Beats, Gigam, I read those things. Daniel- Anything else that you want to convey, things that you see entrepreneurs doing that they shouldn't be, any other thoughts, things that are important? Shai- I think one thing that's really important a lot of folks are talking about is sort of founder issues. Ive seen a couple of start-ups in the past year where the marriage, divorce essentially there are two co-founders and they split up at the really early stage, as they raise that seed round or series A round. I'm not saying it happens frequently, but it is happening and folks don't talk about that in the blog posts. If you re one of the co-founders you probably don't want to talk about it in public but its happening. In part is knowing who you are going into business with a lot of the time this split happens when the company is pivoting, you both agree on where you're going initially and then it doesn't work out. Everyone is talking about leaving the start-up and pivoting, trying and testing that sort of thing. A lot of times they are going in different directions and then the founders disagree on which direction to go. Either go left or go right, so its hard to walk through that unless you are in that situation. People do split up in that really early stage. A couple of other start-ups that I know the founders broke up because one didn't have the necessary skill set to scale the business potentially. I am not sure if that was the other co-founders choice or if that was the investors decision or influence. That sort of thing happens somewhat frequently or they do happen but folks just don't talk about it. I am not sure what the answer is but I think folks who have done business together, you see a lot of companies where there's two engineers they've worked together for two or three years and they have gone through different integrations of the product at Google and they've worked at very stressful situations together in the same group. They know how each one works or they went to school together and they worked on projects together. Daniel- Like junior or senior year. Shai- Yes, I think those folks- it seems like its less challenging because they have gone through that. Suppose you find co-founders that they met maybe 12 months ago through a friend of a friend or at another event, I am not saying they cant be successful, maybe they just will be faced with more challenges. I think having a long history together is important. I think investors look at that as well, investors look at the team and how long they've worked together, what the track record is working together. Daniel- I think we got that question in every single pitch we went to. How did you guys meet, how long have you known each other, it seems like its on an investors minds. Shai- But you had you and your brother. Daniel- Well yeah, my brother Sam is out here is well but the co-founders we've been together for 3 years now. We've worked a lot of those kinds of things out and I can totally imagine how it can be an issue when you are just meeting somebody. I totally get that. I wish there was some kind of a group or a place that frustrated co-founders could go to and try and get support but I don't know of anything. Shai- I have thought about doing private dinners around but it doesn't matter. Folks who have gone through that process of breaking up being willing to talk about it in a somewhat public open setting maybe 10-12 people, if anyone would be interested in doing that. Daniel- Contact Shai if you are in that situation and maybe if you are interested you can set it up. You are going to New York so we are going to lose you out in the Valley for at least a while right? Shai- Yes, I am going to New York in January. Daniel- Alright, so if you're watching this before January and you want to talk to Shai, you better get on it because we only have a few months. Shai- I will be back though. I will be building that bridge between the Bay Area and New York for start-ups. Daniel- That's cool. So there is a lot happening in New York it seems like. Shai- There is. The level of productivity in the last 18 months has really increased and there are questions about whether or not it is sustainable or not because I think New York has gone through these fluctuations of where you get a lot of start-ups and then it sort of dissolves and it gets really quiet for a while. They haven't really had a period where its 5 or 10 years of sustainable growing number of start-ups but in the last 18 months that's taken place its still not 4 or 5 years but there are things around New York that are happening that I think will enable that 4 or 5 year period to take place. That will create some exits, those exits create wealth for the founders who will then invest in other start-ups, who will then create another start-ups because now the second time CEO or founder so its on top of each other and part of it is just the funding that is available now in New York where a couple of years ago there was a reduced amount of funding available. We have the New York firms and then you have the Boston firms that are coming into New York and are very aggressive. Then you have the Bay Area firms and then you have the up and down the Eastern corridor folks in the DC area that are flying to New York so you have a lot of interest of the VC prospective to do deals in New York and those are being done. We have the capital that's a critical ingredient. Daniel- It's interesting to kind of watch a Silicon Valley type of environment try to be jump started in a forum that seems like New York has a good, I mean there must be a trend in your are getting shipped out to New York. Something must be happening out there. Shai- Yes, I think it speaks to what is happening in New York. Me moving out there is not an East Coast, West Coast thing or New York is better than Boston or better than the Bay Area or Seattle whatever it is just that things are happening there. We need to have increased presence in New York and it is really exciting, I think the city still needs that sort of major exit. If you are looking at what is happened to the Bay Area over the last 20-30 years there is always these huge exits. Which then create other entrepreneurs, other investors, engineering talent, most recent one was Google back in 2004-2005 I think that was when IPO was. IPO has really supported this eco-system the last 5 years . Daniel- Its a retro-cycle. Shai- We have all these super Angels, Angels actively investing this pool of engineers that now Facebook has taped into that Twitter has taped into and a bunch of other start-ups have taped into. It seems like New York still needs a huge exit which will create more wealth, more entrepreneurs. Daniel- Well good luck out there. I am sure it will go well and thanks for spending the time to help educate other entrepreneurs. It's a little passion of mine so I really appreciate you spending the time. Shai- Thanks, I really appreciate it. Daniel- Alright, cool. .