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.
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 – http://www.tamccann.com/raising-startup-funding-7-things-you-need-to-be-prepared/
I also love this post, which is very specific and tactical
Today 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, www.rivaliq.com 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 – http://www.yachtingworld.com/blogs/matthew-sheahan/535348/america-s-cup-what-was-changed-on-oracle#lGobZYfDZ42bHg0e.99
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!
In a startup, you are always racing against a clock. Most of the time this is “when are we going to need to raise more money” but can also be working toward key milestones or trying to outpace key competitors, which is often when you need to raise money. And, as you racing toward these milestones, there are lots of things the team needs to track and measure, many of which relate to one another. For example, if you need to raise money, you want to show a ramp in new users/customers, which is usually fueled by an earlier marketing tactic or key product update. So, you need some form of a “startup calendar” that allows you to look ahead as well as track your progress toward the metrics that matter to the company and can be correlated over time. I have developed a lightweight Google Doc as a start to this process and am using it actively in our latest company, www.rivaliq.com (the best way to analyze and monitor your competitive landscape). It is an open Doc, so clone it, add to it, react to it and help me make it better.
Pay attention to time and make measured progress!
First, happy valentines day to everyone and their partner, and a special one to my love, Teresa.
It was 2 years ago to the day that we closed the deal and sold Gist to Blackberry (Research in Motion at the time). As an entrepreneur and a team, we had set out to build the best social address book ever made and wanted to get our vision to the most people we could, as fast as we could, which was our primary motivation on selling the company. The team at Blackberry understood what we had created and where we wanted to go and that was pretty exciting. That said, there were (and still remain) plenty of challenges on the RIM front, but we all dug in with a hope to make Gist the core of a native Blackberry address book. Over the last 2 years there have been many changes including a total re-org and exit of the people who bought us, a change of CEO and many of the senior managers of the company, tons of hard layoffs, and the development of an entirely new operating system, Blackberry 10, which finally launched on January 30. During much of this turmoil, our team remained focused and lead the development of the Contacts app, which has many of the core features of Gist including rich social profiles, most recent updates, company news about a contact and deep integration into the inbox and calendar. While a few of the lead features of Gist (aggregate newsfeed about all my contacts, contact ranking, and the daily digest…) have yet to surface, we are all extremely proud of the work we did on Blackberry 10 and I think its hands-down the best mobile address book on any platform. In addition, many of us have taken on larger roles at Blackberry with me leading the social applications including Blackberry Messenger, Facebook, LinkedIn, Twitter and IM and Steve Newman (CTO) taking on identity (Blackberry ID), analytics and even Maps for the whole Blackberry platform. Some of the team have moved on to start their own companies, take important roles at other tech companies but the team that’s remained has had a big impact on the development process (more agile, less waterfall) and culture at Blackberry (empowerment, “freedom with responsibility”, self-direction, beers in the fridge and lots of ping-pong). It feels good to have started and sold a company where our investors did well, our team did well, the acquirer got good value and we remained motivated and generally happy throughout and we got to realize much of our vision. Like many things at big companies, that take much, much longer than they should or would at a start-up, it is gratifying to see many of our best laid plans play out. I want to again thank the Gist team, our investors Brad Feld and Steve Hall, the team at Blackberry and most importantly the users of Gist and Blackberry who believed in our vision and helped many dreams come true.