Drillin.gs – The Post

Today I’m launching my new blog, Drillin.gs, as a place to share the experiences, learnings and analyses of my time in the start-up world, as a growth-stage VC, as an investment banker, and just in life.  I started my previous blog, VC2BD in early 2011, as someone fresh to an operating role, looking to share comparisons and observations as I moved from what had been a career spent exclusively in finance.  Over the past two years (since moving from VC to a start-up in June 2010), I have held multiple roles (BD & Product Management), experienced numerous challenges and opportunities, and grown tremendously both as a professional, and in general.  Observations I’ve made along the way, and analyses I’ve performed on those observations, have now turned into crystalized learnings.  Drillin.gs is an effort to write about and share those learnings, in order to provoke additional thought by myself and others.


While I may jump around from time-to-time, you’ll likely find some common threads in the content.  In writing each post, my goal is to capture the essence of my learning with hard examples, my own analysis, and any additional works that have inspired me.  In general, my plan is to keep this blog as much journal of my experiences, and how I expect they will change me going forward.  As you might have noticed, the tagline to my blog is “Learning & Burning,” and while that might be a bit unclear at first, I think it fits quite well with that goal.


The focus of my old blog was to give an “other side of the table” point-of-view (which led nicely into VC2BD), while this blog is much more about the overall learnings I’ve had, and whats driving me going forward.  Thus I needed a new name and tagline more reflective of that revised perspective.  My last name (how most people refer to me) was an obvious fit for the URL and main title, and I felt that  a variation on “Learn & Burn” fit the bill nicely for a tagline.  I’ll discuss the individual components of the name below, but first I’ll address the obvious derivation from the term “churn and burn” – a term that conjures up strong feelings for me.  At least in the way that I’ve heard it used, and seen it put into place, “churn and burn” is all about value extraction.  I have an entire post conjured up on my feelings towards value extraction versus value generation, but needless to say, I’m very against value extraction as a method of generating revenue, managing employees and building a business (particularly within the start-up phase).  I fundamentally believe that you can generate a concern of far more overall value with value generation versus value extraction (e.g. gaining value from employees through development & success vs. working them to the bone; ensuring clients generate value in excess of your price vs. collecting all excess value generated).  The Learn & Burn tagline is an attempt to put a positive spin on what has been a very negative philosophy I’ve encountered.


The Learn!


The “Learn” component of the tagline is derived from two elements – both the learning I’ve done, and will continue to do, as an individual, and the learning that is a continual part of building a business.  With regard to the former, as I’ve gone on in an operating role, and continued reading, discussing and researching, I’ve learned a tremendous amount.  Often in this learning, I’ve taken lessons from my engineering education and  my finance / venture capital background, and built-upon them.  I’ve learned much about working with colleagues with broad backgrounds & diverse skill sets, leadership, the importance of focus, business evolution, and problem solving.  I’ve also learned much about myself, and plan to share many of these lessons through this blog.


On the other side of the “learn” equation (and this might sound a bit funny), one of the biggest learnings I’ve had personally, is the power of continued learning in the development of products, markets and businesses.  Its a popular topic around the lean-startup movement, but its also broadly applicable.  In my experience, I’ve been truly amazed by the power of simply getting a product, or even just an idea, in front of people – whether it be through user testing, A/B testing, or by early release.  Testing, and subsequent learning, yields so much benefit; even those with the best intuition can’t predict exactly how a target will interact with a feature, tool or message.  As part of this blog, I plan to share my experiences in this area, and write several posts on the power of learning in product development, marketing, HR, and other areas I’ve touched.


The Burn!


“Burning,” as it relates to start-ups has been popularized by Brad Feld (@BFELD), whose “The Burning Entrepreneur” book / blog collection is fantastic, Fake Grimlock (@FAKEGRIMLOCK), who has a great guest post in that book and is a general innovation rock-star, and others within the entrepreneurial community to represent the “fire” of a visionary entrepreneur.  Driven by passion, and fueled by learnings, someone (an entrepreneur or really any individual) who is on “fire,” drives progress and development in business, across organizations and in society in general.  Their vision is infectious and spreads to others, and in that same vein I’d like to spread my own passion – my life, my business pursuits, and the leanings I’ve done in both – to others, in order to fuel their own endeavors.


As I progress forward, in whatever path I pursue, I plan to keep this blog fresh with material as I continue to learn and grow as an individual and as a professional.  Drillings, the blog, is a journal for myself, as much as a tool for others.  I hope you all contribute by commenting and reaching out.


12. July 2012 by Jonathan Drillings
Categories: Introduction | Leave a comment

Time is too Valuable to be Short

This is a post I’ve been meaning to write for some time now, although the focus and content has shifted as I’ve thought more about the topic.  My original intent was to write about the importance of saying “thank you” to those who provide help or a service in some way.  While I still believe that it is an incredibly important topic and a key trait to have, there are number of high-quality posts and articles that already address the topic.  Nancy Lubin’s article in Fast Company (http://bit.ly/bGp04f) is a particularly good one.


Instead, I’ve decided to dedicate this space to discussing the importance of responsiveness and lending a few minutes of your time to colleagues.  A good portion of my career to date has been spent as either a junior professional, eager to learn from those more senior, or as the newest member of the team, lost in a role unfamiliar to me.  In each of these positions, it’s the individuals that have given some of their own time to aid in my development that I’ve worked the hardest for, and developed lasting relationships with.  In the times where I have been the more senior professional, or the veteran, I’ve strived to give similar respect to my colleagues, and again, have developing lasting relationships with those whom I have shared my time and knowledge.


Taking the time to give employees, junior colleagues and direct reports an understanding of what you’re having them do, why you are having them complete the task, and how much they have helped you by doing it can be incredibly important.  The benefits are not only to the report, but also to the supervisor, who will gain a more knowledgeable and more motivated employee.  When you feel that your boss truly values you as a part of the team, you want to succeed, you want to work hard for them, and you want to advance your own performance.  On the contrary, when you feel like a cog in a machine, disposable to anyone more senior, you’re motivation becomes purely monetary.  Often, once that occurs, you’re likely to work only as hard as needed to secure your goal level of income, or keep your job.  There are many non-monetary elements to keeping an employee motivated, but I believe the most critical is feeling like they are a) learning and b) part of the team’s success.


In my own experience, I’ve worked my hardest, and performed at my best for bosses that have helped to further my professional development, and quite frankly, those that I felt truly appreciated the work I was doing.  And by this I do not mean that they spent every minute coddling me and telling me how great I was doing.  In fact, in many cases it was to the contrary.  Often when you are deep in a project, slammed with work, there is no time for feedback, or even pleasantries.  Frustrations can run high and I’ve certainly had times where I held some animosity towards the same superiors I worked so diligently for.  The difference between those bosses and the others is that after the project was complete, they sat down and gave me honest feedback and assessment; they explained how my work had helped complete the project; and they bought me a beer or lunch to say thank you.  The next project, I worked twice as hard for them.  Here is an example of this dynamic from my own background:


Intern and Mentor

When I was still in undergrad, I had several internships at investment banks.  Each provided a unique learning experience, but one particular summer I learned skills that helped drive my career forward, and that continue to help me today.  That summer, one analyst took to me, and gave me projects that helped me to learn truly valuable skills, such as mastering excel keystrokes and financial modeling.  He spent hours teaching me how to outlay a spreadsheet properly and how to master formulas like vlookup and sumif.  I learned from other analysts that summer as well, but they were often “too busy” to spend time teaching, and I really only learned as much as I took from the work they gave me.  This one analyst really helped to mentor me and further my development, and in fact, when it came time to graduate and find a full-time job, I followed him to his new firm.  There, as a first-year analyst, I worked beneath him in several projects, everyone of which I gave it my absolute all.  We’ve since each moved on to various roles and careers but remain in touch and I’d help him in a heartbeat.


Similar to teaching younger colleagues, a dynamic exists in taking the time to teach newer colleagues “the ropes.”  Nearly all ventures, be it a start-up, an investment fund, or even an established company, require a powerful and effective team.  Even for so-called “A-players,” a support network can be critical to success.  Walking in on day-one to a new job, particularly when it is an entirely new role can be daunting.  Having colleagues that are willing to lend their time to ensure your success builds a collaborative environment and strong bonds between team members.  Employees begin to work as a team to meet goals and to build faster than a group of independent individuals.


In this regard, I’ve had experience as both the newbie and the veteran.  As the newbie I’ve peppered my colleagues with questions, and even though I know I was an enormous time sink for them, it’s those colleagues that spent time with me that I continue to enjoy a fantastic relationship with, and who I rely on in helping to move our product forward.  As I’ve shifted roles, and as the company has developed, I’ve been able to return the favor.  As a veteran, I’ve always tried to remember those that helped me as I secured my footing.  Ten minutes of my time has made the world of difference to the development of someone more junior, and the understanding of process and/or product to peers, and even supervisors.  Overall, taking the time to work with any colleague, and treat them with respect, results in a work environment that is cooperative, fluid and productive.  In my career I’ve also seen the opposite, and in each occurrence, the 5 extra minutes its cost me in time, has yielded significant benefits in the form of cooperation, performance and long-term relationships.


I’ll use a few additional examples to illustrate my point:


Newbie and Veteran

When I joined my prior firm, Investor Growth Capital, I joined as the lone analyst in the West Coast office.  It was a difficult transition from prior roles, and it took me significant time to come up-to-speed.  The senior professionals in the group were all terrific, and are some of the individuals I mention above that I’ve always worked hard for (they were sometimes difficult to work for, but you could tell always appreciated the work I did, gave me candid feedback and spent time mentoring me).  For that I worked hard for them, but it still took quite a while for me to feel like a truly productive member of the team.


After about a year-and-a-half as the lone junior team member, a new analyst came to join the team.  He was a good fit culturally, so we all hit-it-off well, but he and I formed a particularly strong bond.  Coming in, he was as lost as I was when I first joined the firm.  Remember how frustrating that was for me, I made sure to spend the time to teach him the ropes.  I spent hours helping him to learn new equity models, understand team dynamics and feel comfortable with the workflow process.  It sometimes cost me a later night than I otherwise would have had, or having to push my own work aside for a few minutes, but the result was that he came up to speed much faster than I had, and was a valuable member of the team from early on in his tenure.


Senior and Junior Employees

In my current role, I frequently interact with our team of analysts, for whom I’m focused on building software-based tools to help them be faster and more efficient.  The analysts are all fairly young and are junior in their careers, but are intelligent and bring terrific ideas to the table.  Many of these ideas are e-mailed in, or are presented as part of our scheduled meetings.  Some are good, some are great, some are not so great; some are in-line with our vision for the future of the product and some are far removed.  However, no matter what the idea, I try in earnest to give every idea a few minutes and to respond to every inquiry that they have.  The analysts are the engine behind what we do, and my number one source of information on product direction.  I’ve found over time, that the more I open-up to them, the more responsive they are to me – even if I’m explaining why one of their ideas won’t work, they generally appreciate the time I took to write back.  In turn, as they feel like a real part of the team, they continue to provide valuable input, and have always been an incredilby helpful source of insight and information.


At the end of the day, it’s about respect.  If your peers, new colleagues, senior colleagues and junior colleagues feel that you respect them, then they will be more likely to respect you.  Junior colleagues are special cases to be mindful of, where a little time, in addition to some respect, can really help impact his or her experience at the company and professional growth.  In exchange for that little time, a senior colleague will be rewarded with hard work, extra effort and a stronger team.


22. September 2011 by Jonathan Drillings
Categories: Imported from VC2BD | Leave a comment


As those who closely follow this blog already know, it’s been quite some time since my last post.  Unfortunately it was over 3 months ago that I last hit the “publish button,” although for me the time has flown by.  Preparation for the Level III CFA exam took over any and all free time, with multiple weddings, an apartment move, and of course, my work duties, rounding out my days.  However, the insanity is finally beginning to ebb. 


In the course of all these extracurricular activities, and since my last post, I also switched roles within my firm.  I went from Director, Business Development to Director, Product Management – a significant shift (although, no, I will not be changing the name of the blog).  I’m now our product manager for the internal product, which marries technology with the human effort of our analysts, and everything that goes along with that.  I spend about half my time thinking and working through problems at hand and the other half designing and iterating on product ideas. 


I’ve been pondering what to write after this long break.  Given the role change, I thought it most appropriate to provide my thoughts around the differences between the roles and given the title of this blog, also to VC. The point of this post is not just to ramble about some differences, but hopefully to give anyone looking to make a move some insights into the varied roles – the differences, the similarities, and the critital elements of each.  As an added benefit, I’ve included Investment Banking, encompassing my entire professional background and hopefully giving someone in any of these roles a glimpse into the other side. 


To kick it off, below is a chart that highlights some characteristics of the 4 roles.  It’s important to note that 1) this is based on my own experiences and 2) this is relative to an operating business / startup and not reflective of a banker or VC’s efforts in building their own business.  On the X-axis is what I’m calling “Strategic Horizon” – the further out you think, the further you are out on the axis.  The Y-axis is “Operational Depth” – the higher-level you think, the higher you are on the axis.  It’s a crude sketch, not meant to be particularly precise, but I made it in Balsamiq, which I just started using, and so I’m excited to present it.





The Differences

In my experience in VC, thinking was nearly always long-term, and focused at the industry/market level.  We would get to know markets very well – the players, the size and the dynamics – and attempt to invest in the cream-of-the crop management and products.  Infrequently did we get into the day-to-day operations of a business, although earlier-stage guys sometimes get more involved.  Sitting on, or observing, the Board of Directors provided opportunity to play a role in the business, but decisions were made in a high-level, directional manner.  In thinking about investments, strategy was focused on a several-year holding period, with exit expectations set well into the future. 


As Investment Bankers, we thought on a Macro-level.  Bankers often specialize in specific industries, and get to know them well, but its more “technology-level” versus “enterprise software-level” in banking versus VC.  Assignments last a few months to a year, and are therefore not “short-term,” but strategic thinking extends only until the completion of a specific transaction (be it a financing, restructuring, sale or other).  As an entrepreneurial banker you may think more long-term about building a book of business with satisfied clients, but this speaks more towards building your own business than in working with a target company (which often occupies the bulk of your time, particularly the more junior you are). 


As a salesman (we referred to it at Business Development), my strategic thinking was extremely short-term in nature – limited to the accounts I was trying to close that day, and the new accounts I was going to reach out to tomorrow.  Analysis was focused more around the individual sale, although over time trends emerged.  However, through simple participation in a growing company, I learned a lot about our business, the products we were providing, the processes of how we did things, and the competitors we faced.


Product Management, on the other hand, thinks on a longer-term basis, and is more “in-the-weeds.”  There are of course, times when short-term strategy needs to be implemented, but that’s often driven by the sales team, and always needs to be taken into the long-term context of product direction.  No major engineering job is going to be completed in only a day or two, and it takes a long-time to build out all of the features that you envision when you draw up a new idea.  Steps need to be taken one at a time to build properly and only after iterating with your engineers and client base and then really thinking about what’s necessary, and what isn’t, do you draw conclusions about your next steps.  In this manner, it’s somewhat like Business/Corporate Development (as the terms are traditionally used). Thinking long-term about how the shape of the products, or the shape of business partnerships, will affect competitive positioning and avenues for growth.


The Similarities

In considering the differences between these roles, each has provided a unique learning experience.  However, it’s the similarities that I think provide the most insight.  The yin and yang of qualitative and quantitative analysis have been persistent across the roles I’ve held, and I believe are relevant to nearly every job in the marketplace. 


Qualitative analysis has been a significant knowledge driver for my colleagues and me in every job I’ve held.  In each firm I’ve worked for, we looked to learn from people smarter and more knowledgeable than us.  As a banker we talked to potential buyers, analysts, and industry experts.  As a VC we talked to CEOs, industry veterans, and industry customers.  In sales we constantly iterated our pitch against potential and existing customer accounts; and in product management, an open dialogue has been critical to further development of a product set built to meet customer needs. 


The importance of quantitative analysis speaks to the ever-multiplying presence of hard data points.  It goes without saying, but data points are generated everywhere around us – tracked, tabulated and stored in every transaction, interaction and connection made within the digital world.  With applications and platforms like Hashable, Foursquare and Twitter, these data points are even reaching into the physical world.  Every bit of this data can be analyzed to provide insights, and the better one becomes at analysis, the better able he or she is to derive answers by contrasting discussions with numbers. 


A banker evaluates comparables to determine valuation; a VC attempts to measure market size; the salesman uses feedback loops to determine pricing and targets; and the product manager uses customer & usage data to drive product development.   The combination of this quantitative analysis, with qualitative discussions, tells you what direction to point and how best to move your product/investment process/sale process/business/whatever forward.  I didn’t mention it above, but even as the proprietor of a student-owned shipping business in college, qualitative and quantitative analysis we’re incredibly important to our success.  Discussions with clients helped us to tailor our offerings to better suit our market, and analysis of trends helped us to confirm those discussions and also to find opportunities for efficiency and profit. 


At the end of the day, it’s about listening – to data and to people.  Whatever your role, if you listen to what the smart people and the relevant data are telling you, it should point you in the right direction.



30. June 2011 by Jonathan Drillings
Categories: Imported from VC2BD | Leave a comment

Startup Lessons from an Unusual Source

As some of you know, I’ve spent the past few months, and will be spending the next few months, studying for the Level III CFA exam.  While it may seem counter-intuitive that someone writing a blog called vc2bd.com will also be taking a finance-focused exam, my participation in the program is rooted in my banking background.  I first decided to enter the program as a second-year banker, and took the Level I exam in 2006.  Having an undergraduate engineering degree, I had a great quantitative background, but never felt that my finance and accounting skill-set was as strong as that of my finance and economics degreed colleagues.  I decided to take Level I as a way to build those skills.  In 2007, I had just moved out to San Francisco, and with some extra time on my hands, decided to continue the program with Level II.  In 2008, I shifted into Venture Capital and with a large work-load and a long commute, decided to defer the Level III exam.  Now that I’m back in NY, I’ve decided to complete the program.

While most of the material we cover is uncorrelated with life in a startup, there are actually a few lessons from my studies that mirror lessons from the startup world. While not perfectly analogous at first glance, they actually line-up quite nicely when you dig-in. The power of review classes, the creativity of derivatives, and the harmful practice of Style Drift are a few of these lessons.

Review Class

Each Tuesday this Spring, I head over to a professional classroom on 53rd and 7th for a 3 hour review class.  Each class is meant to re-enforce the material studied independently the prior week, through discussion, examples, and in general, just by taking a second look.  Sometimes I leave class feeling like I’ve learned a tremendous amount, and other times, less so, although I’ve never left feeling like it was a waste of time.  The simple act of taking a step-back and reviewing the materials I had studied the prior week, often with a different perspective, has helped me to fill-in blanks and generate a more complete understanding of the material.  Additionally, a second time through the material often makes me realize better ways to attack the material and simply just being in a different atmosphere helps me to absorb information in a different way.  Its not unlike a college class, although having been out of the classroom for a half-dozen years, these classes are somewhat of a renewed experience for me, and I go through them with a slightly different perspective then I did back then.

I think that startups (and really any organization) should take similar steps to “complete the picture.”  Periodic reviews of your activities let you take a step-back and look at things with a fresh perspective.  Strategy sessions outside the office, and away from daily activities and grind of the office (or wherever you work), can function much the same as my CFA review classes.  Breaking for the normal rhythm gives you an opportunity to think about what your doing, absorb what has happened over the past few weeks or months with a fresh perspective, and let you more easily plan for the future.  At IGC, we did a team off-site at least once per year, a group off-site at least once every two years and a firm-wide off-site once every three years.  It was a fantastic time to review and plan, while also spending time with colleagues from other offices.  


One of the recent topics reviewed in class were derivatives, a family of financial instruments that have gotten significant heat over the past several years, and rightfully so.  The recent collapse in the financial markets was driven much by derivatives.  However, it was really propelled by the abuse and misuse of derivatives – using things like credit default swaps in ways they were never intended and retraunching CDOs to create high grade security classes out of low grade securities.  However, when used correctly, creative thinking around derivatives can be a powerful way to reduce risk and change the nature of a portfolio to better fit the investor (such as when you have a large debt portfolio and want to diversify into equities but can’t afford to incur the transaction costs).

In much the same way, creative thinking can be a powerful tool for start-ups to maintain lean, cost-effective growth.  Obviously any start-up needs to be creative in its business-model order to succeed against incumbents or even more so, to forge a new industry, but it also helps in day-to-day operations as well.  As I wrote in my last post (http://bit.ly/fRsUFz), having excellent individuals that can provide several functions for the organization and successfully fill in gaps can be critical to building a lean and efficient business.  Brainstorming and coming up with creative solutions to IT, communications, management, marketing and other aspects of the business can mean the difference between high-growth with motivated employees and burning through capital while treading water or even drowning.

Style Drift

Similarly, the lessons learned in the manager evaluation sections of the CFA curriculum, in particular, those sections around Style Drift, also provide an important start-up lesson.  Investment managers are typically hired to focus on one asset class (e.g., large-cap equities or investment-grade debt) and Style Drift simply means that an invesment manager is slowly moving into investments that he or she is not supposed to focus on.  This can cause problems for the portfolio manager who hired him or her, as there will likely be cross-over with other managers in the portfolio, and he or she may simply not have the capability to work beyond a certain expertise.  

In much the same way, its important for start-ups to avoid Style Drift, and to keep focused on their core business.  While its important to maintain the ability to change course or “pivot” into a different direction, a gradual dispersion of focus on the product portfolio (beyond means and before the product is proven out, of course) will likely hurt the business.  With a lack of focus, the engineering team can become overwhelmed, the product team can be stretched too thin, and overall communication to other areas of the business will likely suffer.  Its important to maintain focus on the core business to help drive the business forward and prove out the product or service, while avoiding situations where new business lines are introduced and compete for resources before the originals have either taken hold, or have been dropped in favor of the new.

Overall, these weeks of studying the CFA material have caused me to think a bit differently about not only the finance profession, but also business in general.  These are just a few of the similarities I’ve seen thus far.  I’ll likely write another post on the subject later on in the Spring, or after I’ve completed the course and taken the exam.  As usual, please comment below and let me know if you think I’m right-on, partially there, or completely off-base.



23. March 2011 by Jonathan Drillings
Categories: Imported from VC2BD | Leave a comment

Wearing Many Hats

Having come from a finance background, I had always worked with individuals of similar background to myself.  I don’t mean background in the sense of traditional demographics, as my last office had team members from around the world, but more with regard to skills-set and professional background.  In finance, a focused set of backgrounds made sense – we were purpose built for investing.  In a start-up, at least at the early stages, it’s seems so important to develop a team of individuals with a broad range of skills.  The diversity allows you to recruit from a broad talent pool, while ensuring that the company has the flexibility to manage itself, execute efficiently, and produce rock solid products.  Essentially, since you need people to wear many hats, you want to make sure that the hats fit.

At IGC our team was relatively homogeneous from an experience perspective – good education, several years of investment banking or PE grunt work, and then onto IGC.  For an organization with a singular focus, such as a late-stage venture capital firm, it was a terrific group – incredibly intelligent, easy to work with, great to learn from, streamlined, and very efficient.  We had a singular purpose, and, in my opinion, we executed that purpose quite well.

As I’ve realized in my brief time at a start-up, a narrow background set would prove a detriment to the organization.  At my current company, many of us do have that same great education, although our backgrounds post-college vary broadly.  Of course, simply the nature of a technology company brings together business-people with engineering, but the backgrounds of those individuals must be broad enough to sustain the business through the early days.  The engineers must often function as the IT group and sometimes the product managers; the business-people are the sales group, the operations group, the product management group and, quite often, the first-line legal group as well.

Of the colleagues I work closely with, there are some originally from the start-up world, as well as former lawyers, former consultants, former bankers, former investment professionals, current and former engineers and, given our business, many recent graduates.  After this experience, I couldn’t imagine attempting to build a startup without a broad range of backgrounds.  Of course, it goes beyond just the utility of having (for instance) a former lawyer to do the first draft of an agreement.  We all look at problems in different ways and have different tools to solve them.  As an example, given my engineering education, I problem solve in a different way than my colleagues with economics degrees, who problem solve in a different manner than my colleagues with law degrees.  With a wide range of backgrounds, a small skilled team can replicate the work that would otherwise require several different divisions. 

Additionally, while your customers are going to ultimately drive the direction of the product, and getting it into their hands early is the best way to garner feedback and thus product development, you have to start somewhere.  Having team members who can weigh in during the initial consideration, design, and development of key features (and sometimes even product sets) empowers you to more fully flesh-out product considerations, features and future direction before going to market.

Personally, as a member of the business development team, I’ve used the PowerPoint and Excel skills garnered in my prior finance life to help generate marketing materials and firm wide presentations – tasks atypical to a salesperson.  I’ve also weighed in on some product design, and have also started to run our SEO/SEM efforts.  My business development colleagues with former start-up experience have helped to develop our products and have even begun to generate additional products.  My colleagues with legal backgrounds have expanded beyond their operations and business development roles to help strategize as we focus our products on that market.  Without that blurring of the lines, our product and company wouldn’t be nearly as robust as it is today.

Lastly, I’ve realized how important it is to keep early-stage recruiting open to individuals who are passionate, intelligent, and capable, even if their background isn’t a 100% fit.  The bottom line is that you want good people.  Passionate, intelligent, and capable individuals can usually morph into the role and in doing so, also lend their experience to provide significant value across the organization.  I assume that with continued growth the lines between groups will begin to crystallize, and new hires will be more specialized, but I believe that the versatility of the early group will have formed the basis for future growth.  

24. February 2011 by Jonathan Drillings
Categories: Imported from VC2BD | Leave a comment

Time Management

I always knew that start-ups were busy, and that start-up employees had a lot on their plate.  However, coming in from a venture capital fund (where 12 hour days were average), and before that investment banking (where the guy that left at 11pm was taking-off early), I thought that the move to a start-up would actually be less time intensive.  In fact, it wasn’t until I got here that I realized what busy truly was. 

If it’s not following-up with a potential client or trying to generate new leads, we’re generating presentations, interviewing candidates, launching new initiatives (like our SEM efforts and newsletter efforts) and overall just thinking about general business strategy.  If you layer in general time-sinks like an overabundance of e-mail, keeping up with news, etc., there simply isn’t enough time in the day/week/year to get it all done.

In trying to combat that schedule, I’ve started to think about and utilize a few techniques for time management.  I have a friend whose firm has introduced SCRUM development methodology into their business efforts, and that’s potentially an option, although difficult as a sales professional in this start-up environment (primarily since you always need to be responsive).  I used to use e-mail separation (just simply turning outlook off for a periods during the day) while very busy at IGC, and it worked wonderfully.  You simply don’t need to be that responsive in many industries, and it really helps focus, but it’s much harder to accomplish when you are on the sell-side. 

I’ve have, however, found some products that have really helped my productivity, starting with my android phone.  The move from blackberry has been a good one; although I’d imagine the new torch could probably do much of the same things my Droid X has done for me.  Here are some of the things that have really helped to revolutionize my productivity since I joined the start-up world – most of which involve a shift to new cloud-based tools:

Wireless Hotspot – apart from separating myself from AT&T, this was the single biggest reason I decided to go android over iphone.  Of course, now the iphone is on Verizon and has this as well, but that’s another story for another day (although if the iphones don’t get LTE this summer, I’ll be sticking with android).  In any event, this thing has saved me many times.  Apart from the multiple meetings I’ve used it in, I’ve used it on the train, in airports and when the internet was down in our office.  In doing so I’ve saved numerous hours that would be otherwise worthless.  I’ve always had my blackberry set up to be teathered, but this is just far more convenient and applicable to more than one device. 

 Dropbox – I’ve been hooked on Dropbox since my days at IGC.  Given that much of our technological backbone was based in Stockholm, our VPN never worked seamlessly and so we started using Dropbox to aid in sharing files between computers.  In my new role I continue to use it to sync up various computers, and have started sharing folders with my colleagues as well.  We have a “share drive” but it is only accessible within the office network.  Having the capability to share beyond our walls makes traveling and working remotely far more productive.  Additionally, with access on my phone and ipad, I can quickly look up documents on the go.

Evernote – I started using Evernote about 2 months ago and I’m hooked on this program as well.  I used to find the memo tool in outlook (which then synced to my blackberry) quite helpful, but evernote takes that a step further.  Rather than retyping notes after hand-writing them, I can take pictures and upload them straight to Evernote.  I jot down themes and ideas as they pop up and overall it keeps me focused, with relevant information right at my fingertips.

Pulse – A fantastic newsreader that a friend just turned me onto.  As a VC, reading the tech blogs were always part of my job.  Now that it’s not part of my job, I have less time to read things like TechCrunch, VentureBeat, etc. although I’m still interested nonetheless.  Pulse allows me to read them whenever I have a few minutes to catch-up, along with sources like the New York Times and others.  Unfortunately the NYT syncing isn’t great, and it doesn’t seem to sync with it google reader – if that came it would really be one of the best products ever.

Thunderbird – it took a while to set it up, it occasionally has hiccups, and its not as robust as Outlook, but its far far far faster.  Thunderbird syncs better with google apps, which we use for our e-mail system and quite frankly, just works and works smoothly.  When it does have hiccups, a simple (and quick) restart seems to bring it right back to life.  On the note of e-mail, while I’m not in love with the Google apps interface (hence Thunderbird) the syncing capability and ease of use through multiple access points (thunderbird on my computer, gmail through any browser on any computer and gmail on my phone) is very convinient.

Commuting by train! – while this isn’t exactly a technological solution, having formerly driven between SF and Menlo Park each day, it is revolutionary.  The commute is still decently long out to Newark, but having the chance to just sit on the train makes a huge difference – I can catch up on everything from the news, to work, to just relaxing and zoning out for a half-hour.

I just started using a new tool as well – Summify.  I find it interesting, although hasn’t been that helpful so far, as much of what I get through it I’ve already read.  It’s likely best for days when you are on otherwise completely out of pocket and come back ot a full inbox and an ocean of twitter updates.  I’m also keen to start using Greplin, which just came out, to easily search through all of my online life.

I’m always looking for more tools to use and would love suggestions.  


15. February 2011 by Jonathan Drillings
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Sourcing vs. Prospecting

While at Lake Street, and as part of my role at IGC, I spent a significant amount of time investment sourcing – going out and talking to potential counterparties in order to develop new investment opportunities.  When I was at Lake Street it was corporate venture guys & treasurers and venture capital CFOs.  When I was at IGC it was start-up CEOs and founders that I was talking to.  Sourcing at Lake Street and IGC involved research/identification (to find out who was best to contact), cold calls/e-mails (to generate leads) and relationship building.  I occasionally utilized my network to develop contacts as well.

In my new role, as a business development professional, my primary role is in sales, and therefore sales prospecting, is a critical part of my job.  Each day I’m identifying, cold e-mailing/calling and developing relationships with prospects.  I go through a similar process prospecting as I did investment sourcing and of course, while interviewing and when I first arrived, I assumed these were basically the same thing.  I quickly learned that my assumption was far off. 

While investment sourcing wasn’t easy, and I often had difficulty reaching my targets, at the end of the day I was usually able to make the connection.  In sales prospecting, I’ve had no such luck – multiple calls go unanswered, e-mails are unreturned, and meetings are impossibly difficult to set up.  The key difference being money, and more specifically, money-flow.  As an investment professional, even if I was calling on someone who had little interest in talking to me at a particular time, I was still part of the buy-side and eventually it probably made sense to talk.  A CEO who was too busy to answer an e-mail when his company’s bank account was flush with cash, was often readily available when it was time to raise a new round.  I was calling to introduce IGC (or Lake Street) and propose an investment, but ultimately the dollars were flowing towards my sourced contact and so if they were “buying,” they were really selling. 

In my current role, I’m selling a product – quite simply asking people to exchange cash for our product.  So even if I find someone with a pain point that we can provide a solution to, I still need to convince them to part with their cash.  It’s an extremely difficult process, and in this market, even more difficult than usual.  Once you get people on the phone, usually they are nice enough to give you a few minutes – occasionally you can grab them via e-mail if you send enough of them (and occasionally you find someone nice enough to respond on your first outreach).  To get them to trial the product is another story entirely, and of course, that is only the first step – the trial is no-risk, and while many do convert, its a true sales process all the way through to the end.

In general, as a vendor, it’s extremely difficult to get people to call you back, e-mail you back, respond to notes, etc.  In order to get responses I try to be as engaging and constantly in front of them, while at the same time trying to be as hands-off / not-pushy as possible.  So far I’ve learned that you only have so many shots on the goal (people’s time and attention) to get your introduction across, and so it must be tremendously appealing, and pitch incredibly pithy.  If you get their attention, you need to keep momentum-up – once they disengage and move towards other activities they quickly lose attention.  Once their bandwidth fills with other projects, its very difficult to get them back.

If nothing else, my foray into sales has taught me extreme humility and the ability to quickly forget dismissal.  One of my former colleagues at IGC once gave me a bit of advice – “Always assume that the guy on the other end of the phone wants to talk to you, they are just busy” – which I’ve relied on even more in my current role than ever before.  You won’t always get a response, but as long as you continue trying, you might get a few.  And of those few, some will turn into trials, and a few ultimately clients.  We’re not only selling a product, but evangelizing a new type of service – keeping my head up on outbound sourcing has been incredibly difficult, but in the end I think it’ll be worth it. 

In my short time in sales, I’ve realized that it truly is one of the hardest jobs in the world.  Having to put yourself on the line each day and with each conversation is nerve-racking, frustrating and humbling.  I have a newfound appreciate for salespeople of all sorts, including entrepreneurs, who go out and sell their vision and dream each day.  Its important to remember how much of themselves they pour into each coversation, keeping a positive attitude throughout.  I certainly salute them.


08. February 2011 by Jonathan Drillings
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About 6 months ago I left my VC Associate role at Investor Growth Capital (IGC) and joined an early-stage startup as Director, Business Development.  Soon after, I decided that I wanted to start chronicling my experiences as I made the jump from investment role to operating role.  I thought others might find it interesting as well, and so I decided to start this blog. 

I’ve loved the first several months in this new role.  Of course, I’m busy as I’ve ever been (which is why I’m just now starting this blog after joining in the summer), but I feel like I’m making a real impact.  We’re a start-up in the information services space, servicing a wide range of clients – including investors, traders, analysts, bankers, lawyers, investigative services firms, PR firms, corporations and the research and professional services groups that serve those groups.

In my role I’ve gotten to meet and speak with individuals within a number of those groups and have really learned a lot about their roles and the type of information that they seek.  I’ve also gotten to interact with a wide-range of successful professionals (including our own founders) primarily through our advisory board, develop marketing materials and manage our SEO/SEM efforts (more to come on that later).  The first few months have been extremely interesting and I hope the next several months continue to be.

04. February 2011 by Jonathan Drillings
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