There are a couple classic archetypes of internet/software founders, including the genius college student cooking up something quirky but ultimately disruptive in his dorm room who launches his company straight out of undergrad. But the other archetype is a thirty-something entrepreneur who, taking his experience seeing the playbook of success at larger growing startups or even “established” companies, utilizes that domain and functional expertise as unique insight into founding a company. This latter persona is still hungry, but is able to really leverage that experience-set.
While a year ago there was much ado in the blogosphere about the peak/best age of an internet entrepreneur – whether it’s someone under 30 with fresh de novo thinking – there is some statistical support that the successful thirty-something entrepreneur is actually more prevalent. Anecdotally, you can point to examples here as well (Zenstrom / Skype, deWolfe My Space, Hoffman / LinkedIn, Williams / Twitter were all in their thirties). In reality, there is no “best” age to start a company, but rather different cohorts produce different profiles of entrepreneurs and resulting companies. (And at NextView Ventures, we’ve funded both young entrepreneurs out of college as well as veteran executives in their forties, along with a range in between.)
One historical challenge with the Boston entrepreneurial scene is that while we have a continually refreshing supply of the nation’s brightest coming out of our local prestigious educational institutions, for the better half of a decade in the 2000’s we were both losing people coming out of school, plus we had fewer of the second set of thirty-something internet entrepreneurs referenced above. Two years ago Jeff Bussgang lamented about “Lost Generation” of entrepreneurs which I think is especially acute here in Boston.
My own personal story fits in with this narrative. I was in my early 20’s just barely out of school when four of us (peers) started Sombasa Media (aka BargainDog) here in Boston beginning in 1998. We rode the bubble wave to a successful outcome in 2000, and after moving away for a few years which included a stint at business school, I returned back to Boston in 2004, and it felt like the web entrepreneurial community had almost entirely scattered after the crash. Reactions when I told people I was an “internet entrepreneur” ranged from smirks to blank stares.
In only a few short years, the strong pillars of the local Internet scene, like Lycos & CMGI (+ affiliated companies), had fallen away and been rendered irrelevant. Along with their demise came a dismissive attitude about most entrepreneurial web-related endeavors. It surprises me how little this fact is talked about in Boston, but there was a vacuum left behind with these potential powerhouses withering away. If you had a few ounces of entrepreneurial blood in the late 90’s, of course you started an internet company (for better or for worse). But from the middle of the last decade onward very few peers of mine were starting companies because they hadn’t had the opportunity gain that valuable experience like they would have had at Yahoo then Google on the west coast -or- they were dissuaded from negative experiences during the crash and a challenging atmosphere after. Instead, they had fled to other industries and those other geographies. My own motivations for starting the Web Innovators Group in 2005, and the reason I believe it took off so quickly, is that there were relatively few people in the community, but those who were all yearned to congregate and find a similar network of like-minded individuals.
Today the landscape is very different from 2004. First, there is an organized community net which is better (although certainly not perfect) at “catching” raw entrepreneurial talent out of the universities and keeping people here in their 20’s. Recent initiatives like Startup School are easy examples to cite, but there are numerous programs including the proliferation of networking events which have laid an infrastructure support to help keep the next Zuckerberg from slipping through the cracks. But second, we’ve also had a number of internet successes which have trained and developed people (e.g. TripAdvisor, Brightcove, Constant Contact, Wayfair) over the past few years where employees are beginning to roll out to start new ventures. And the larger imports (Microsoft, Google, eBay… recent challenges not withstanding) have now been established for a time that people have had at least a few years to formally train in internet software product development areas. And so that second cohort of thirty-something entrepreneurs is just now emerging as a solid group because there have been places for the internet skillset to develop. For example, it’s much more prevalent today in 2012 to have been a tactical internet marketer for the past five years whereas in in 2007 is just wasn’t. There is also now a third cohort, though still rare, of awesome people who have had entrepreneurial success experience during the 90’s boom now building truly transformative companies later in their careers who had moved away & returned, who eschewed a venture capital role after a brief stint, or who had been doing it all along. Plus, on top of it all, with accelerator programs we’re net importing kick-ass founders from all over the world. But last of all, attitudes have changed – you CAN build a great internet company here in Boston, and we have a community which sincerely believes it.
So in Boston, it’s essentially taken a decade, but we’re finally overcoming the crater that the failed local internet giants left behind after the 90’s bubble. There are now three strong cohorts of internet entrepreneurs ripe with ideas & passion who are deliberate about staying here & building the center of the universe for emerging platforms. And that certainly wasn’t the case when I moved back here in 2004. With real clusters of strength in areas like mobile, marketing, and consumerized B2B SaaS – Boston is entering a golden age of internet entrepreneurs positioned for the future.
A few days ago, a friend who works at a growing startup emailed me with the following question (in which I’ve masked just a few of the identifying details):
- I caught up with a friend of mine from high school that has started a new company where my skills are very pertinent. He wants a data scientist to come do some work for them, and while I’m intrigued, I’m not ready to jump ship and join them 100% of the time. I am, however interested in throwing 20 hours a month into helping them out, possibly helping them recruit some talent when/if they need a full time analyst, etc. We’re close to formalizing some sort of relationship.
- Here are 3 questions that come to mind: 1) We’re using this document from the Founders Institute as a template and guide for comp. I’m curious if you think this is ballpark okay. 2) Are there any risks to serving as an advisor that I might not be thinking about? 3) Any other advice or experience with advisory relationships? I’m definitely not in the rainmaker category that I think a lot of young companies look for… in the short run I’ll be more like a part-time employee than an advisor, but expect that will change if the company moves forward.
My email response to his question was:
- On your questions below, it sounds like a good situation. You’re able to spend time with the company during its early stage to do some interesting work, explore if there’s a good fit for you there in the long run, and be compensated for the efforts which you’re putting in. The compensation framework and contract template are reasonable (though of course I am not a lawyer).
- But broadly speaking, I think that there are two risks/issues to be thinking about. The first is around your eventual role/compensation if you’re likely going to join full-time. Spending 20 hours a month is fairly significant amount of time. If in a few months or a year, you decide to take the leap to 100%, you’re of course want to negotiate an equity relationship which is more appropriate for that role. Unfortunately, your equity is already going to be anchored <1% depending on where the company is today. At that time, you may not have as much leverage (with the company or whatever their current/future investors) to meaningfully increase that amount to the same level where you would have come in if you started the conversation today about equity comp commensurate with a start working part-time yet with a specific path to full-time. The risk is that you’ll look back having put in meaningful time into the company and all-in not feel like whatever additional package they can offer you is worth it. Yet you might not want to make that personal commitment/signal today, which is also reasonable. The closer this role is to a part-time co-founder versus a later employee, the more acute an issue it is.
- The second risk is a contractual + relationship issue with your current employer. Depending on what you signed when you started your job, you may be prohibited from moonlighting, or at least required to disclose it. It’s up to you given the overall situation and your own point-of-view if you want to share this role with them. I think the worst-case scenario would be one where you eventually join this startup and your current employer finds out that all along you had a (potentially violating) contract in place with this startup and then jumped ship to them – they may not take kindly to that. Again, it all depends on your relationship and how you manage information.
After completing a long process identifying the right venture firms to pitch, running an exhaustive fundraising process, finding a mutual fit, and successfully negotiating terms… at last, the term sheet is signed. So at this point it’s OK to just hand the process over to your lawyers, sit back, and let them work out the details, right? Wrong.
The two- to six- week time between the signing of the term sheet and closing is “venture limbo.” At this point, entrepreneurs know who they’re going to be working with and along what structure, but the deal isn’t done yet… including wiring of the funds! Most of this time-period is taken up by lawyers drafting and then negotiating the finer legalese points of the full set of legal documents. But it also includes legal due diligence, rounding out the round with additional syndicate investors (often angels in seed rounds), figuring out allocations, as well as sometimes even (but hopefully not) additional business diligence for the institutional venture investors.
The problem is that time kills all deals. The longer this limbo period extends, the more risk is introduced that the process will veer off course or even fall apart entirely. It should feel like things are accelerating towards a close, as opposed to marching along at a steady pace; and it certainly should not feel like deceleration towards the end.
The possibility of negative scenarios adversely affecting the outcome range all the way from some uncontrollable exogenous disastrous macro event (of which there have been a few major ones in the last dozen years) to the possibility of a venture firm simply getting cold feet and backing out. Obviously, only the latter is within the locus of control of everyone involved. It doesn’t matter the reason – a competitive funding announcement, a customer loss, a bad month of results – with more time, the increased chances of more emerging mitigating factors to getting the deal completely finalized. And even if the relationship with the VC partner leading the investment seems solid, entrepreneurs have little window into his partnership political dynamics during that time which could force him to lose his hold on pushing the commitment over the line.
What can extend the month of limbo? Lawyers going back and forth on minute/inconsequential details, of course. But frequently, there is time spent negotiating business terms which weren’t specified in the tern sheet itself. Founder vesting is the most common example. Or sometimes VCs renegotiate terms or introduce new concepts – nefarious, but I’ve seen other firms exerting their negotiating leverage in a relationship given this situation. And I’ve seen weird unpredictable situations crop up that delay things, too. As an extreme but real example, once a standard background check which was run on the startup’s CEO reported that someone with his exact name from his exact town was a felon convicted of embezzlement. It turns out it was literally the wrong guy, yet same name / different person, and the entrepreneur was asked to sign an affidavit maintaining it wasn’t him. But the whole cycle delayed the closing and almost derailed things because of the uncertainty.
The good news is that these scenarios don’t happen often. At the end of the day, a VC signs a term sheet for a reason: they’re making an agreement under the circumstances which they’re eager to do. The job of the entrepreneur is to ensure those circumstances don’t change too much in the interim. And most VCs (including all of us at NextView) pride themselves on their reputation about keeping their word, not backing out of term sheets or renegotiating after they’ve been signed. But the takeaway here is that the fundraising process isn’t complete until the money is in the bank.
Like a lot of students, I went into business school a decade ago with a set plan to start a company coming straight after graduation in co-founding an internet startup (… again). During the following two years I did a number of things which prepared me for that endeavor, but then also in retrospect, I completely missed out on a number of opportunities and valuable resources immediately in front of me which I didn’t recognize at the time. My alternative working title for this post was: “Eight things I kind of knew and only mostly followed as an entrepreneur during b-school.” My own circuitous path graduating a couple years later intentionally without a job (see bullet #1) eventually led me onto the venture capital investing side of startups, but I still regret not fully taking advantage of the two years that only a business school environment (and calling card) can provide. Recognizing the academic year is starting now for MBAs (as well as all other entrepreneurial-minded students, for that matter), I wanted to articulate a set of recommendations for b-school students looking to start a company immediately after graduation:
- Commit to graduating without a job. It’s a challenging leap of faith to take, but entrepreneurship requires a full all-in effort. If it’s there’s an irresistible urge to hedge a bit in exploring alternative paths or engage “just a bit” in on-campus recruiting for traditional roles, then it’s better to fully pursue one of those routes (at least for now) than be distracted by an entrepreneurial pursuit which won’t materialize.
- Master the coursework basics, but then develop soft-skills rather than specialized ones. Part of the benefit of a generalized MBA program is developing a broad fundamental skillset across many areas of functional expertise, from finance to marketing, and everything in between. After those core skills are developed, however, it’s more advantageous to spend additional classtime developing higher-level softer skillsets which will be used throughout the entrepreneurial process rather than deeper point-solution “hard” expertise which can be hired or learned on-the-job as needed (e.g. take Interpersonal Dynamics not Global Financial Reporting.)
- Take classes from the best “star” professors. You’re paying quite a bit of money for this education, and the different between star instructors and the solid overflow ones is step-function not incremental. For example, Irv Grousbeck and Mark Leslie at the Stanford GSB fundamentally changed my thinking about life and business, and unsurprisingly Felda Hardymon has the reputation for doing the same at HBS. Regardless of school, there are always the premier professors. Use your entrepreneurial drive to go around “the system” to get into those specific classes – beg, borrow, and steal to do so. Camp out at their offices. Or just show up for the classes and literally take the course twice, once with the star (unofficially) and the “standard other” instructor officially. It’s worth it. Really.
- Go outside the business school to meet co-founders. Business schools are very insular islands, but they’re surrounded by an ocean of students in all disciplines. Your developed skillset won’t be much different from your immediate classmates’, but it certainly will be from someone in engineering or computer science. “Recruit” your co-founders there; it’s more difficult, but that’s the point. Diverse thinking will create better thinking.
- Go off-campus with your student ID. Your “student” calling card immediately disarms and can open all sorts of doors which won’t be as inviting the second you have a diploma in hand. Proactively and persistently reaching out to people directly who could add insight and credibility, as well as potentially initiate a process for company-making deals, for your startup. In our NextView Ventures portfolio, Eliot Buchanan (Founder CEO of Plastiq) was the master of this approach and was able to bring on high-profile partners (think: Mastercard) to his business before even graduating from undergrad!
- Immerse yourself in domain to develop authentic idea. Rather than whiteboarding different potential business ideas, think about your own previous work experiences to solve problems for constituents in that business which you know first-hand. If nothing comes out of that exercise, spend time truly immersing yourself in a specific industry or domain.
- Do what you’re classmates are not. MBAs are notorious for sheep-herding towards a particular category of startups (recently, daily deals and online new e-retailing). Aim for the upper right quadrant on the the consensus/non-consensus vs. right/wrong 2×2 matrix and develop a (hopefully correct) thesis that’s not following a common assumption.
- Take a summer internship to hone expertise or a functional skillset, NOT for resume padding. Once you start a company, nobody will care what you did for ten weeks one summer. Really. But the chance to just drop into a company and industry for a couple months, without any strings attached, can help develop real knowledge and facilitate connections. For example, in the NextView Ventures portfolio, Fred Shilmover worked at Salesforce.com before starting SaaS-based InsightSquared straight out of school… and now Salesforce.com is an investor in the company, too.
- Find yourself. Taking two years out of the workforce before fully pursuing an entrepreneurial endeavor grants a luxurious amount of time for self-reflection. Utilizing this time to better recognize and appreciate not just your strengths and weaknesses, but also your underlying motivations and intentions, will help prepare you for the many challenges of starting a company.
You’ve just closed your seed round. Other than starting to build, hire, and take over the world, there are a bunch of mundane things to do right away. The following is a first pass at a checklist of items for Founder CEOs to take care of in the first couple weeks after they’ve closed their initial round of seed funding.
- Figure out your PR strategy for announcing the round to get your plan in order.
- Remember that a number of reporters scan Form D filings for fundings which include notable venture firms in order to preempt funding “scoops”; talk to your legal counsel about the timing of your own filing.
Communications with New Board & Investors
- Ensure all of your investors have all legal documentation of the round, including an electronic version of the final cap table.
- Figure out a Board of Directors meeting schedule & cadence acceptable to everyone joining in person. Publish dates & times in advance for the next nine months so it’s set in everyone’s calendar in order to avoid the hassle of coordinating scheduling multiple parties every month or two.
- Proactively solicit input to create a board deck template and metrics dashboard to present at the first Board Meeting, so that you’re able to set a strong in-control tone.
Foundation for New Employee Hires
- Formulate and socialize with the Board acceptable compensation bands (both salary and equity options) for new employees. This best-practice will help set expectations all around about the compensation-level for hiring, so that there will be less need to consult the Board on standard hires, only for executives which are exceptions.
- Hire a firm to conduct a 409A valuation to set a strike price for your employee stock options, which needs to be at or above “fair market” value.
- Explore HR/healthcare/payroll options… as it’s entirely likely you’ve held off formalizing to-date but now will need these in place for attracting and hiring employees.
- Obtain Directors & Officers insurance; you and your fellow Directors want it, and your docs may necessitate it.
- Switch to more than just a bookeeping firm (or upgrade from merely Quickbooks); instead engage an accounting firm so that you don’t have to think/worry about it down the line. But a full time CFO and even a CFO-for-hire may overkill at this point.
- Send a personalized thank you note to the half-dozen people outside the company who helped you during the fundraising process.
- Take the whole company (presumably pretty small at this point) out for a Thursday night drink – you have a lot of work ahead of you but it’s worth it to celebrate together in achieving this first fundraising milestone of many to come.
Please leave additional suggestions in the comments, and if there’s a critical mass of content, I’ll likely repost the blog in the future.