Twitter for entrepreneurs – the why and the how of growing a following

I was recently asked to talk to a bunch of budding entrepreneurs about how to use Twitter to grow their own personal brands and therefore additional value to their companies.  The presentation talks about the “why” and the “how” to achieve this and includes some very cool stats from other “social CEOs”.

Answering The Anvil – startup questions from Purdue entrepreneurs

The_Boiler___The_AnvilI went to Purdue and studied mechanical engineering.  It was an amazing education and prepared me in many ways for the work I do now as a software entrepreneur. (technology, software development, critical thinking, data>>opinion, math…).

Recently, I was contacted by a student looking for an internship.  A few emails and an “audition” later, we hired Spencer Brown for the summer.  I applaud his networking (reached out to me directly on LinkedIn), willingness to work at a startup who might/might not be able to hire him back (risky internship) and openness to work through our process or lack of one.  We were specifically impressed with his hacking/building things and proven entrepreneurial interest vs. just school work. We @rivaliq are looking forward to seeing him this summer and building cool stuff for our customers!

Then I was contacted by Grant Gumina, the managing director of, a co-working space at Purdue. He asked me to help out some of the teams who were going through (accelerator) and I happily agreed.  Prior to the talk, I asked him for some frequently asked questions, and while I answered them during a recent Skype call, I wanted to share for the benefit of others.  Here goes;

What’s a recurring mistake have you made that took you a while to figure out?

Doing customer development AFTER I made a product vs. before.  Now, I spend lots of time, focused talking to potential customers using only a hypothesis on what solution I might build to frame the conversation. It’s about asking questions vs. telling them what I made (marketing) and why they need it (sales).  I want to understand as much as I can (problems, existing solutions, buying behavior, influencers, pricing options, keywords…) about a customer segment, as early as I can, and this informs many downstream decisions.

Not understanding the funding sources early in the process.  Talking to investors early, is a useful part of understanding a market as well as when/if I can raise money for a specific idea and the metrics/progress I might need to achieve to get the best investors.  Here is how I think about it now;

Not understanding similar or competitive solutions, again, early in the formation of the idea.  It’s hard to change user behavior so understanding the best solutions in the market today and how ours could be 10X better (enough to dramatically change behavior) is important.  I now do this as soon as I start working on a new idea, often using tools like Rival IQ to understand the existing companies, then triangulating with discussions with customers and investors to get a full picture of the landscape.

What would you do if you were in college again?

I was at Purdue for 5 years, 4 of which I was swimming full-time (on scholarship) as well as being a mechanical engineering student, so I was pretty busy. For my 5th year, I won a scholarship (Red Mackey Award) and was able to spend more time really digging-in and learning vs. just getting by.  For engineers and other technical majors, I’m sure you are equally busy so there is not much time to do “more”.  But, I wish I had spent more time with people who were out in the world doing what I thought I wanted to do.  This could have taken the form of projects or internships but more importantly, trying to understand what people DO on a day to day basis via coffee/short conversations.  In retrospect and looking at my career path, this would have been much more time pure entrepreneurs vs. more corporate roles.

Secondly, I was a proficient programmer, but I would have have spent more actually get “good” in a way that I could have landed a job in that area as well as mechanical engineering.

Finally, more time with designers.  This could have been in graphic design, product design… with a focus on understanding how they think, their processes, how they make decisions….

If your question was about my major, I think ME was a really good foundation.

How do you start to charge users if you’re already giving them the product for free?

This is always a tricky thing, but I would think about it in a few ways.

One, just start charging and let the chips fall where they may.  End users should understand that you need to make money too and that they’ve received your “value” for free.  Be honest with your users and just communicate openly.  The best ones will want to pay you so you keep bringing them value vs. quitting to go work on something else.

Another idea is to pick a set of features which are highly requested, from your best targets (not all users are created equal) and then only charge for these new features leaving the base product alone and remaining free (lead gen).

Another angle is volume based, which means you get to X of something for free and if you want more of X, you need to pay.  See Full Contact Card Reader as an example.

What’s the best way to engage beta testers/early adopters throughout the development process?

I have a longer blog post about this here, but the simple answer is;

  • know who you want and overly focus on a smaller set of highly engaged users.  These will be people who “really, really” want their problem solved and ones who are “experi-mental” meaning they are used to using products early in their lifespan and when they usually suck.

  • blend online means of interacting (email, chat, twitter…) with physical interactions (have real people come to your space and use your product)

  • Build in customer development and feedback into your sprint/development process so you are always meeting new potential users (at least 2-3/week)

  • Give public credit to people who give you ideas, e.g.  “thanks to GrantG for the idea for X” – Put this in release notes, blog posts, tweets…

  • As you get a basis working product, consider some “community” support solutions like or or even a hacky google doc where users can report bugs, suggest features…

  • Focus on “customer success” vs. sales – this means knowing about lots of other solutions in a space, that solve problems for your users in your narrow domain (e.g. Syncing your contacts ( or understanding your competitors ( as well as the broader domain (business productivity) or (digital marketing).  Share suggestions, posts, ideas, solutions widely.  Be a useful resource, even when your product is not the right fit.

  • Suggest content and connections – “you should really read X, follow Y or try Z and if the user is valuable or influential, make connections.

What things have you really wasted time on early in the company’s life?

Focusing too much time trying to convince users that they had the problem I was trying to solve vs. focusing my effort on solving for the people who self- identified and were really wanting a solution.

What strategies or tools do you use to stay productive?

At work, I am a major user of software tools and utilities.  Much more detail and specific tools are here –

I am also still very active and try to exercise for at least 60 minutes/day, usually longer.  I also make sure to get at least 8 hours of sleep on one or more nights each weekend.  Usually only sleep 6-7 during the week. I also eat largely vegetarian (sometimes fish, but no meat) and have done for over 25 years.  Spend at least a few hours each week helping other people, giving advice, sharing what you know…mentor others even when you think you might not have that much to offer.  Just “help-share”.

If anyone else wants to support the cool work they are doing at Purdue, connect and share;

Creating a perfect seed round with Leads, Follows and Random investors

For a startup, raising a seed round is a daunting endeavor.  Techstars Seattle Demo Day is looming and I recently finished mentoring the teams at the Kaplan EdTech Accelerator so advice on fundraising is top of mind. I’ve written about fundraising before here and here, but I recently saw Brad Feld (who is awesome and was an investor in my last company) give a great talk that added a few great words to the lexicon – Leads, Followers and Random investors.  So, borrowing from Brad and adding my own ideas, here are a few things to consider when putting together that perfect seed round.

First some definitions;

Leads – Usually professional investors, who write > 5 checks/year at $100-500K/deal to fund startups.  They are experienced in the dance, the terms, know lots of other investors…and know how it all works.  They negotiate with the entrepreneur and help set the terms for a round.

Followers – These are majority of the investors you will meet.  They either don’t have the time, money, expertise or fortitude to lead a round. These people usually have a day job and are investing as a hobby, a way to engage with startups or to support the startup community.  If they are “active” they usually do at least 4-5 deals/year.  I am a follower and am very clear about it with companies but many other investors are not so clear.

The overall fundraising process should be planned (e.g. I hope to close by the end of the year), with a solid understanding of how much you want to raise (e.g 750K-1M), with what vehicle (e.g. convertible note) and under what terms (e.g. 4M cap, 18-month term and 20% discount).  Much more on terms here and in Brad’s book Venture Deals.  The clearer you are, the faster the round will likely come together.  

With this plan, you have a sense of the amount you need from a Lead investor, usually >25% of the total raise.  You also have a starting point for negotiation when you get the lead investor in the room. Now your job is to go find the LEAD!

In a best case, you will also have some idea of the domain expertise (e.g. “marketing tools”) and/or functional experience (e.g. content marketing, channel sales, product development…) of your desired investors and you can ultimately create a “tapestry” of people with complementary skills and backgrounds to add to your company.

When you start talking to investors, spend time asking questions to determine a good fit.  Ask them directly;

  • How much do you normally invest/company?

  • How many deals/year?

  • What thematic areas are you most interested in?

  • When you invest, how do you like to engage with the company?

  • When you have invested in the past, were you a lead or a follower?
  • In addition to the money, how else do you like to help your companies?

An experienced investor (the kind you want) will be totally comfortable with these kinds of questions.  They too are about expediency, getting to a YES or NO as quickly as they can and not wasting their or your time.  Depending on their answers, you will get a pretty good sense of the kind of investor they are and in the best case, how likely they are to invest in your space and whether you think they can really help the company.

Assuming you think there is a good fit, continue the discussion about the business, opportunity, specifics…to get to a “yes, I think I would like to invest”.  If they are a Lead, you can start working a term sheet, if they are a Follow, “collect” them for later and communicate this to them, something to the effect of “Hey T.A., I am really excited to work with you and I think you could add real value to our company.  Right now, I am focused on finding our lead investor to get to solid terms, but I would love to pencil you in for (X, depending on their answer to normal check size) for the round, how does that sound?”  At this point, consider them “soft-circled” and get back to finding the lead.

Followers are not likely to become leaders, no matter how much you try to convince them.  Too many entrepreneurs spend way too much time trying to make this conversion happen.  If someone, who has not lead before, wants to step up, probe on experience, skills, desire… and plan to invest more time with them and your lawyers to get to a solid term sheet, but this is not the desired path.  You really want an experienced Lead.

After many meetings, you are likely to end up with a collection of Followers and finally, a LEAD!  Woot!  Get to a term sheet, get the Lead committed and then start closing the Followers.  Depending on where in the process you found the Lead, you may have a long or short list of potential Followers.  Part of the job of the lead, is to bring more people to the table and in most cases they have many people who they’ve co-invested with before.  Ask for introductions and use their leadership to close other people.  Assuming the lead has 25-50% of the round, Followers might close out the round or at least get to 75% before you need to go back to the well and look for new investors.

But wait, there’s more.  As you you diligently move through your known prospects, getting people to commit, “random” people will show up and express interest.  These are likely people who have heard about you from some other investor, another entrepreneur, a press article…but they feel random.  As these investors are coming late in the round, you should have momentum with lots of others signed up, closing these Random investors much more quickly.  Otherwise, rinse and repeat the process above, but be OK with Random happening.

Finally, fundraising is a sales process so you need to keep momentum going with lots of prospects, closing when you can and continuing the conversation with others being clear, consistent and regular with your communications.  Focus on the right things, the right people, the right process and you will close those Leads, Follows and Random investors to fund your own next big thing!


Telling your startup story with .xls vs. ppt

Troy Henikoff is the managing director of TechStars Chicago.  I recently saw him do a great talk outlining the tools and strategies around building your financial models.  Lucky for you, the Techstars team in NYC, where Troy spoke, videotaped the whole thing, but I thought I would pull out a few key points and add a bit of my perspective too.

As entrepreneurs, we all make PPT slides to tell our stories, which is basically required.  These slides get the broad story across and should be used to get prospective investors engaged in the business.  But, the smart investors will quickly want to understand how you plan to run the business, what choices you need to make when and what impact these choices will have on the core metrics of the business.  These choices are best examined and communicated in a set of financial models and they are critical if you are to impress good investors and run a successful business.  Time to study up!

Troy does a masterful job of showing you, through a presentation and example spreadsheets, how to build the models, what assumptions to make, how to challenge these assumptions inside your team and then with investors.

A few key tips;

  • Use Excel vs. Google Spreadsheets.  Excel is more powerful, will allow you to take real snapshots and is “the language of a professional financial world.”

  • Use simple, clear “labels” on your spreadsheets.  This makes is easier for everyone to understand what you are talking about as you move around different sheets.

  • Build the models yourself – you need to understand your business, how the model works, what are key assumptions, when you need more cash…you can get help in structure so it meets standards, but know your own model.

  • The most important number on the model — revenue.  To create long-term sustainability, you must be growing revenue, preferably quickly.

  • Know how to take an investor through your model in a way that is concise, clear and methodical.  This will instill confidence and build a solid foundation for working together.

  • The one thing you know about your model is that it’s wrong, you’re just not sure where, yet. Your job is to make it and then find the things that are incorrect as you keep running the business by comparing the model to actual, usually on a monthly basis.

Troy does such a good job on the slides and the presentation, I won’t try and cover all the points, but I highly encourage you to download the docs and watch the full video.  It will be worth it.

Full video is here – (multiple segments, so keep watching)

Copy of presentation and sample docs are here –

Changing context creates new learning

Last week, I participated in The Meeting in Aspen, CO.  I was invited by my good friend Christopher Jerard who is former editor of Freeskier Magazine, Rival IQ customer and all-around good dude working with some amazing clients in action sports.  The event, held annually for the last 10 years, is about getting smart people from the ski and snow sports industry together to compare notes, learn from each other and plot a course for the future.

The event was fun for me because I don’t know the industry, the players or the issues despite an occasional trip up a chairlift.  I did a talk about “Learning from your Competition” which included my background in sailing, the 2013 America’s Cup, current work in marketing analytics and some future scenarios around quantified self.   It was fun to try and bring a fresh perspective and at the same time make my experience relevant considering my affinity for the liquid vs. crystalline form of H2O. I hope the group took a few things away from the talk including the ideas around “build– measure — learn” and measuring “me vs. me, me vs. the competition and me vs. best in class”.

After my talk, I had the chance to meet lots of great and inspiring people including Chris Davenport who, after doing some amazing skiing is working on climate change with Protect Our Winters and Jeremy Jones (also involved with POW) who was showing off his latest movie Higher.  These guys were seriously inspiring on so many levels and I was blown away by their accomplishments.

I also had the chance to talk with Chris and Rob from Outside about their recent work and was especially excited about their upcoming Volvo Ocean Race coverage.  Chatted with guys from X Games, GoPro and other major brands to learn how they are producing and promoting such amazing content across lots of different channels.  We also hang out with Troy and his group from Resqwater (very cool chemistry lesson) which might just end up being the next drink sensation!  Finally, Deric and the crew at Aspen Snowmass organized a great mountain bike ride on the new trails up behind the airport.  Let’s just say that living at sea level vs. altitude creates a disadvantage and I got totally smoked on all the climbs but it was beautiful and fun.

I learned a lot, made a set of connections that challenged my thinking and gave me new perspective on many things including the limits of human performance.  I hope I get more invites to unexpected places to keep learning from smart and inspiring people.  Thanks for having me!

Your best team is a blend of fit, skills and domain expertise (in that order)

Finding the right team members (2)

Building your startup team is the most important thing you’ll do in the life of your company.  The team includes the people who work on it every day as well as your advisors, investors and in certain cases, partners.  At Rival IQ, we are hiring for a marketing leader and another developer to add to our team, so I have been thinking about the best approach and I believe it’s a blend of fit, skills and experience, in that order.

Fit – Doing a startup is hard with tons of stress, long hours and a million decisions. Finding people who have similar value systems, approaches to living and problem solving is critical.  There are no absolute right answers on fit.   Different people fit into different situations and many great people will not fit your culture.   I suggest creating 3-5 statements or philosophies about the company that attempt to define you and your culture and therefore better assess fit.  My friend, Rand Fishkin, at Moz has created this Tagfee, which pretty clearly articulates what they care about.  Bart Lorang at Full Contact openly expresses things they value, some of it illustrated in his post about “paid, paid vacation“. At Rival IQ, we are developing our own culture using phrases like “freedom with responsibility” (self-motivated),  “data drives decisions” (analytical and specific), “everyone has a voice”(respectful and opinionated), “a team that works out, works out” (healthy) and “it takes a village” (family, friends and community matter) and correspondingly we can approach “fit” for new people. As a founding team, you should also determine bigger issues like “what does success look like” (lots of impact, lots of money, building a big company, building a fun company…) as this will determine fit for potential team members and drive much of your ongoing decisions.  Write it down, evolve it (I suggest quarterly or with a funding milestone) and test your culture with people you think you want to hire and make sure they fit while at the same time really understanding your own company.

Skills – Every company has a set of goals and tactics they need to employ to achieve them.  Skills are how you get shit done.  Time also usually equates to more skill as people get better as they practice.  Think hard about what needs to be done and what critical skills are required.  Hire for these.  Also, hire for people who can demonstrate the acquisition of new skills (learners).  “What did you learn over the last year?” “What do you want to learn in the next 6 or 12 months?” are good questions to test for this.  The best people come with demonstrated, quantifiable skills but are very good acquiring new ones.  Map your skills into the business needs for the next 3-12 months and fit it into the puzzle of what you already have on the existing team and don’t overweight into one category.  Skills, of which learning is one, are second to fit in importance.

Domain experience – Most valuable industries are moving fast so deep industry knowledge can be as much a curse (these are all the ways this won’t work) as they are a blessing (here’s how we can work the system to our advantage). The key is to find people who don’t overweigh their domain experience and take from it the opportunities to lead and re-invent. Also, as you move more toward B2B or complex selling or PR/marketing where industry connections and relationships are important and take a long time to foster, the value of domain experience is higher, but still falls behind fit and skills.  If you are hiring someone for experience, work hard to see how their connections translate directly to the things you need to achieve (usually customers, partners or other people).  If the line is not clear, run away.

This approach of blending fit, skills and domain experience applies to your advisors (I recommend 2-3) and investors too.   Some investors want you to be frugal, others spend like crazy.  Some want you to focus on people and systems, others not so much.  Some care more about the technology, some the customers, some the growth.  Some are happy with an early exit; most want only a home run.  Some will want you to work 100 hours/week while others think it’s a long haul and you need to stay fresh, happy and rested.  Like fit, there are no “right” answers here, just different ones, but if you end up with mis-matched values and expectations you will spend more time fighting than building the business.  Brad Feld and Steve Hall were investors in my last company and we all really “fit” so building the business together was fun, rewarding, stimulating and very productive.

Hiring and building a team is an art and takes time.  Start hiring early, before you need people, by defining your values and finding the people who fit, who have the core skills to do what needs to get done.  Focus on fit, skills and domain, in that order!


The startup fundraising cookbook (8 steps to raising a solid round)

I do a significant amount of startup mentoring and I’m often asked about fundraising. Like many things, I’ve tried to develop a process and decision-making criteria. There will always be exceptions to every rule and the odd startup that can raise a round without much preparation, but the vast majority will require focus and discipline to get it done. Here’s what I recommend.

1. Pick the right time – In my opinion, there are only 2 good times of the year to raise money, spring (February-June) and fall (September-November). For the other times of the year, most people who have money (angels and VCs) are off vacationing in fancy places, and getting them to make decisions or coming to consensus is really hard. So, decide when you will be ready to raise money. Your story and pitch should be ready in early February or September depending on which window you’re targeting.  Redpoint’s Tomasz Tunguz has some data to support this and suggest the fall is the best window.  Work your plan backwards from this timeframe.

2. Pick the right amount – early stage funding tends to come in 3 flavors: angel, seed or Series A. Angel rounds tend to be $250-500k, seed 500k-1M and Series A 2-5M. There is some variance depending on the stage of the company and the specific investor, but for plannings sake, decide on an amount. How much you should raise depends on a few key things: what you need to take the business to the next level (usually 12-18 months runway) and your overall progress compared to all the other things the investors can fund.  You can also check out Tomasz’s  post (can you see I am a fan of his) which describes the right amount to prepare you for a Series A. Most good angel or seed stage companies have some working product, a small, but growing amount of users, maybe some revenue, a solid founding team… and if you don’t have these, it will be hard to raise a round.

3. Find the right investors (before you need to raise money) – once you’ve picked a timeframe and a general amount, you can start building a list of prospective investors. Focus on; a) Geography – Depending on where you’re based, there are likely investors in your geography who are active (at least 4 investments/year). Look at other companies in your area that have recently been funded (at the same stage) and who invested in them. b) Domain – every company has a “category” they’re working in and it can often be expanded to fit into two or three categories. For example, Rival IQ, which provides competitive analysis for companies (my current company) is a b2b company focused on “marketing tools”, “analytics”, “social media” ,“business intelligence” and “competitive intelligence”. With the categories, start listing all the companies who’ve been funded and by whom (investors). Crunchbase and AngelList (which share data) are great for this work. You should end up with a list of companies, their current investors, locations of the investor, amounts invested, and timing of the investments. Combine the lists (geography, category, comparables),  and you will end up with a solid list of investors who are likely to invest in your space, in your area and at your stage. Rank them by who you like best, who has best success and/or where you have connections or history with the particular firm or partner. Separate into “A” (guys you really want) and “B”(people would be fine, but not the best).  The B list will be your pitch practice guinea pigs. I tend to have groups of 10-15 investors in A and B.

4. Understand the marketplace – this involves knowing the competition and market comparables. I tend to use a combination of Rival IQ  (quick and easy competitive analysis on positioning, seo, social stats…), a MindMap and a spreadsheet for this work. I basically want to compare a) who’s in the space that directly competes with me, b) who might as we grow and c) who might if we get really big (or who would buy us or the competitors along the way).  This will give you another list of companies and investors and start to arm you with; “we are similar to X (recently acquired company where investor did well), but unique in these ways…” Investors are great at pattern matching and you need to illuminate the relevant pattern that you fit in. This list will also inform you of the level of acquisition and metrics you might need to move from level to level. Below is a snapshot of a MindMap I did for my recent Rival IQ fundraising.RivalIQ fundraising mind map

5. Draft your “story” – considering the timing, the amount, the investors, the marketspace and your own plan of what and how you want to attack the market, you can determine what kind of story you might want to tell. There are various levels and different kinds of progress that can support an investment, and different investors will care about different things in these early days depending on the kind of business you have. For example, when I was raising money for Gist (my last company), we had some investors who were deeply interested in the product (Brad Feld/Foundry), and some others who were more interested in our monetization, and still others more interested in our viral growth of users. All of these are reasonable, just different, and would have required a different story (and proof) of our progress. For Rival IQ, we wanted to tell a story about “validated customer demand” so we targeted >30 paying customers by Sept 15. We also wanted to keep showing customer growth and breadth in demand (verticals, geography…) and, while our story included a strong team, a big market, a cool product, we led with “validated customers” with reasonable $ and $/customer and targeted people who liked that story. Pick your own story and start building supporting data, metrics, comparables… to support it.

6. Connect and test, refine, test – start making connections with funded founders (who know investors) and with the targeted investors (from your list), and testing your story/hypothesis. Unfortunately, this is the hard work of finding ways to get introduced by people who know the investors and will vouch for you. This is a major value of accelerators like Techstars. I would start with the “B” group  and test the story. Get short meetings with something like “I am doing X, plan to raise money in the (fall) and wanted to start building a relationship with you now. Given that you have so much experience in this space having invested in A, B and C, I wanted to get your take on Z (very succinct problem you are wrestling with).”  Be very tight, very narrow on your questions and listen. What did you think of the response? Was it helpful, specific, logical…and did it help you make a hard decision? If you like the feedback, say thanks and ask if they want to receive updates on your progress. If not (and you will get lots of weak and non-specific answers or advice), say “thanks, that’s valuable input and I will consider that as we move forward” (whether you will or not). In any case, try to limit the first meetings to 30 minutes and let them ask you to stay longer, otherwise you both can get back to your email. If there is strong interest, ask what specific kinds of progress (metrics, growth, product, team…) they have seen from their last 2-3 similar investments at your stage. Try to quantify what you should look like in the future and then you know what to work towards and how likely it is to achieve.

Side note: good investors will not likely invest in you if they are already invested in one of the other players in the space.   If you contact them, be very upfront if you think there might be a conflict.

7. Send regular updates – I suggest sending a monthly investor (or prospective) investor update. Bcc people on the list. This is likely to be about one page long (email) and include key items like major wins, product updates, key metrics growth, team additions… It should also provide simple ways for these investors to help, like “looking for an intro to X guy at Twitter” or “looking for great blog posts on SaaS metrics or growth hacking…” Good investors want to help, but you need to make it really easy for them at this stage. Listen and respond quickly if/when they engage. Keep doing these even when you think nobody is listening as it shows commitment, communication skills, ability to build a tribe… You can send these to advisors you meet along the way too as they will often be your conduit to investors. I get about 15 of these every month from companies I’m helping.

8. Assemble the investor puzzle – when you are finally ready to raise the round, you should have a good idea of the potential investors. This may include the skills or domain expertise you really need to help the business get to the next level, and/or the people who have added lots of value along the way. Focus first on getting a lead investor, who will likely take 25-50% of the round. You can gather the followers later, but focus more on the lead as they will dictate terms, structure, timing…and you don’t want to need to go back to the followers over and over as things change. Secure the lead, collect a few followers and target 75% of the full round you want to raise. With this in hand, outline the specific areas where you are still lacking. For example, at Rival IQ we had our VC lead (Vulcan), our solid seed/CEO people (who can help us better run a SaaS company) (David Cohen, Startup Studio) and some people representing our customers (social marketers like Jay Baer and TerraLever) – that got us to about 85% of the round. We wanted more social platform players so we got someone from Facebook and then added the founder of Hootsuite, who has a trifecta of deep Twitter understanding, deep social and SaaS experience and agency background.  Boom!! We have 2-3 small spots left and we are being very targeted about who we want and why. The latter investors often come quickly once the leads are in place and fill out the overall puzzle for a great round.

Generally speaking, the round will take you 3-4 months if all goes well and will take the CEO 50-75% of his time. If done well you will end up with a collection of people who complement the business and the founding team. From there, your job is inform and activate them to help grow the business. Good luck.  And, once you get a live one, here are few things you might need to be prepared –

I also love this post, which is very specific and tactical

How winning the America’s Cup is like building a successful startup

AP6893762757241-1024x599Today Oracle Team USA won the 34th Americas Cup, staging one of the biggest comebacks in sailing, and maybe sporting history, fighting their way back from an 8-1 deficit to win 9-8 in the best of 17.   It was an amazing success and show of skill, engineering excellence and perseverance, all things that go into a building a successful start-up.

I know both sides of this scenario, as I was part of the winning AC team in 1992, (America3) and my last technology company, Gist (acquired by Blackberry in 2011) was considered a solid win in the startup world.   I see many parallels between these wins and the Oracle victory.

Start with a vision
When you enter the AC, you need a solid vision and strategy on how you think you can win.  This usually starts with a hypothesis on the key areas of innovation on which you can create an advantage.  In sailing, this could include boat design, sail design/construction, weather planning, computer modeling, crew selection…and a host of other potential ways where successful innovation will create speed.  For example, in 1992, the team had a hypothesis that we could literally invent a new kind of sailcloth, made of carbon fiber that would be significantly lighter and stronger than then current standard.  As we look at this year’s AC72s, there were lots of areas of potential innovation with a new class (catamarans vs. monohulls), new sail types (wings) and even different types of sailing altogether (foiling).   And, in startups, you have the same approach; picking a market, considering competitive advantage or innovation and creating a hypothesis around what you might build and the edge it will create over your competitors.  In Gist’s case, we believed we could build a better contact manager, by connecting to your email inbox and using that to help define your most important contacts (people you email a lot).  And, using that list, we could surface important and relevant information about them from news, blogs and social content.  We believed this would be valuable for business professionals the world over, all a vision and a hypothesis at the beginning.

 Build a great team
With a basic strategy and set of ideas in place, you go about finding the best people and experts in the world to design and execute.  This usually involves engineers, and the best ones are in short supply or are being snatched up by your competitors. For any of you technology execs, sound familiar?  In the AC, the pool of people is smaller and with the new catamarans and wing sails, expertise is even more limited than normal, so the competition for the top talent was pretty fierce.   Oracle had a big advantage, as they knew more about the rules and guidelines before everyone else (the advantage of the Defender) so they were able to snap up the best talent and get to work on building stuff.  Once you have unique talent, it’s harder for the other guys to innovate in the same ways.  Who you hire and when will be a critical factor on which things you can build and how quickly you might create an advantage.

Get solid funding
To win the AC, it takes a pretty big pile of cash.  By some calculations, Larry Ellison invested over 100M dollars to win and we invested over 40M in 1992.  That money enables recruiting for the best talent and lots and lots of experiments.  Like venture capital in the startup, capital allows you to tryout many areas, thus increasing the chances of a breakthrough.  Same same.  And, when you get good VCs involved in your deal, like I had with Paul Allen and Brad Feld, you gain confidence in hiring, in investing, acquiring… where you can to create gains.  I knew, that if we needed more cash to pursue some crazy ideas, we had their support.

Test and iterate
Most people only see the end result of the work, the event itself or the exit.  What they miss is the months or years of grinding it out, working toward a solution.  In startups, this is usually thought of software development, broken down into small iterations, we call “sprints”.  In these sprints, the team picks a focus area, innovates as much as possible and then “ships to production”.  In some areas, it takes many sprints to get to the full extent of and idea realized, but you approach it in small, focused chunks.   In the AC, this is the testing phase, which can last years before the event.  We (or the team managers) pick an area of focus (say the design of the keel/dagger boards).  We set up 2 boats (A/B) and we try different combinations to see which ones are faster.  To be accurate, the sailing team needs to keep as many of the other variables constant (wind, waves, sail trim, concentration…) to get to a result of which keel/dagger board is actually better.  The decisions are aided by lots of computer monitoring and number crunching, but it still takes the teams focused on every test, for weeks on end to make the most efficient progress.  This is just like sprints and A/B testing in software development. It takes “focused persistence” and a special breed of stamina and attitude.

Make big, hard decisions
Along the way you need to make lots of decisions.  Did we test this variable enough?  Can we move on?  Did the other guys make better gains in this area?  Can we afford to make another attempt and try something totally different?  Deciding what experiments are yielding early and potentially game changing results and which ones to cut/kill is a very difficult.  Experience, intuition, pattern-matching and a solid team all play into making these decisions quickly and in a way that the team supports.  Some are likely wrong or made too early, but the teams ability to make hard calls and unify around common goals and to charge forward with confidence is crucial to success.  In 1992, we had lots of hard choices, setbacks and rebounds.  For Oracle, they made a hard choice to change tacticians late in the game, but you could see the team (at least on the water) did not lose a beat, stayed focused and pushed on.

Learn from your competitors
Every good market has worthy opponents who, in their own way, are attempting to lead.  In some cases, you can determine where they’re focused and what success they may be having.  In other cases, it is very hard until you get to the starting line.  My latest startup, is all about learning from your competitors.  During this AC, New Zealand came out with an edge.  They’d been the first to really figure out “foiling”, especially when at maneuvering the boat.  This was a design and boat handling innovation and they were fast.  They won 6 or the first 7 races and took a commanding lead. Most, including me, thought the lead was insurmountable.  Oracle went to school, studied what the Kiwis were doing and improved, changing their boat and their handling.  They got better every day and by the end, were significantly faster than Team New Zealand.  A team of lesser character or skill could have given up or given in, but they stayed focused and kept refining.  A common trait of great companies, they watch and learn, always improving and outlasting their competitors.

Update (9/30/13) Here are more details on what Oracle may have changed on the boat. Very smart –

All the planning and skill is important, but to be really successful, some things just need to go your way.  During this AC, several days of wind limits (too much wind to sail) gave Oracle more time to modify-race-test-modify the boat with only one (vs. scheduled two) race per day.  They got faster.  And, on day 13, New Zealand leading 8-2, needing only one win to clinch victory.  They were leading by a wide margin, the wind died and they couldn’t  finish the race before the 40 minute limit.  Seriously, that sucks? Lucky for Oracle, devastating for New Zealand.  It was a key turning point in the regatta.  When we sold Gist, there were many fortunate circumstances that aligned to make it happen, many of which we didn’t control.  It involved a good deal of luck. 

While my experience is correlated to doing a startup and winning the AC, Larry Ellison knows many parallels as well, referenced here in a solid article in Forbes and detailed in the most recent book The Billionaire and the Mechanic.  I sailed with Larry and the team on Sayonara too and he is an intense competitor.  He and the other members of that team made huge sacrifices, personal and financial and put it all on the line in an attempt to win.  It often takes that same commitment from the entrepreneur and the teams to make it happen when it looks like it won’t work, when the vision will fail and all the work for naught.

At the end of the day, it is about creating something so good, so fast that, even if you switched the crews, your boat (or company tech) would still win as we did in 1992, with Gist in 2011 and as Oracle did in 2013.  It’s exciting to be part of the history of the AC (winning and losing) and to be part of the lore of successful startups too.  I am fortunate, committed and sometimes lucky.

Congratulations Larry, everyone on Oracle Team USA and to all the successful startups who are demonstrating focused persistence toward victory!