Category: Venture

Mike Maples of Floodgate Talks VC & Start-ups on the Origin Podcast

Mike Maples of Floodgate Talks VC & Start-ups on the Origin Podcast

Listen to Mike Maples on the Origin Podcast here

It was one of the better venture-related podcasts in the past few months. Here are my notes:

Risk-Return: Get paid for your risk

  • The reality is that every profession has a top 10%
  • Managers are too reliant on anecdotal wisdom as opposed to first principal or theoretical basis
  • Get paid for the risk you take in two ways
    • Invest before the Series A firms (series +1 firms)
    • Getting ownership at a lower price basis
    • Get pricing power by not competing with big firms at pre-product market fit: get a real chance at ownership here
  • All investing, fundamentally, is how you get paid for the risk you take

Understanding Competitive Advantage: Playing Offense

  • After getting in early, where else is your money competitively advantage?
    • Pro-rata rights
      • If you are Benchmark or Sequoia, you get to see Floodgate and Founders, Baseline and First Round deals. They have more optionality on what deals to do.
      • It’s their specialty to do Series A and Series B deals
    • So, follow-on should primarily be exercising your pro-rata rights and for the most part in Seed deals
      • Index the top tier Series A firms;  and most (seed) funds overestimate their follow-on investing skill and spread too thinly. More often than not should overindex to these deals.
      • And many firms are not applying the same rigor to follow-on investments. When you see (seed) firms doing Seed extensions and Seed 2’s the firms are incorrectly assuming their money is still competitively advantaged.
      • On as theoretical basis what is it that you know that the market doesn’t know? Why is your wisdom greater than the wisdom of the crowd? The exceptions are:
        • Company crushed numbers and is inflecting. In that case the preemptive strategy works and you add-on before going to market
    • Always play offense with your money and when it is competively advantaged
      • Invest before others care (seed)
      • Pro-rata rights that the rest of the world doesn’t have but only I have
      • I know something on the tip of my tongue that the rest of the world doesn’t know yet (the pre-emptive strategy)
        • Hoping for the best is not an example and this is where most firms that do Seed Extensions or Seed-2’s overcommit to resere
Fund Operations Reserve strategy
    • Angle 1: ”Do you have high enough conviction to go super pro-rata? If not then its a no-commit”
    • Angles 2: Follow-on investing is more like index investing, versus picking investing. “Picking” is an infinite range of companies/ options. But follow-on investing is you investing from a fixed pool of companies. So in this case, is my wisdom greater than my wisdom of the crowds? And index investing assumes no unless you know something you are sure you know. “The problem most investors in follow-on scenarios believe they know something that are not so: intangibles of Founders, board insights, etc. But I give the market a ton of credit for figuring out the best performers.”
      • With lack of quality upstream interest, be careful to think you know something the market doesn’t know.
      • Be sure you explicitly know something differentiated.
  • “Your fund size is your strategy”
    • Successful start-up outcomes are a rare event: 10 companies out of 1,500 seed deals create 90% of the returns. Power law distribution
    • Fund portfolios within the Funds themselves also follow a Power Law distribution (more power law oriented with Seed as opposed to Series B/C)
      • So to aim for a 3x Fund and you assume a power law distribution, then the top deal is 1.5x your Fund, your second deal is 0.75x and your third deal is 0.375x, etc. All totaling to 3x.
      • And when the best company has to return 1.5x the Fundf by itself, you do the math: $100M Fund means the best deal returns $150M. And if your average ownership stake is 7% then one company has to be worth $2BN.
      • When your billion dollar exits dont return big for you, you have a problem.
Forecasting as a Strength (Book mentioned: superforecasters)
  • Amateurs can outpredict professionals in forecasting if:
    • Continuous forecasting
    • Intellectually diverse team
    • Process everyone believes in
    • Write down what they believe the truth is to the best of their knowledge at the time; AND revisit and ask the tough questions: what is surprising us and what has changed and what is the new truth with the new facts
    • GOAL: Don’t get too attached to being right individually. More about getting to the right answer for now, cumulatively.
  • As venture investors, they forecast for:
    • Pace of investing (deals, dollars)
    • Average deal size
    • Average price
    • Ownership
    • Expected reserves
  • The more uncertain a future is the more valuable the forecasting process becomes
Buffet and the Strike Zone of Competence
The art and science of hitting (baseball) is to know your “circle of competence” and where you hit best. (If a ball comes within a certain region of the plate for Ted Williams then he hits 0.450 –  And then in another part of the plate, if he took a swing he would bat 0.130) So the art and science of hitting is knowing your circle of competence, and then having the rigor to only swing at balls in that circle of competence.
In investing, there are no called strikes. So in theory you have the opportunity to invest only when a deal is inside of your circle of competence. In order to do that you have to know your circle- and that takes a few Funds.
One observation is to go back in time and ask: what are the best [seed] deals done and if so are we at a Fund size and strategy that matches that adjusting for new truth that we believe?]
Takes a while to get better at follow-on support. Everyone starts overly-optimistic. Need to adjust and temper expectations.
Seed: More of a people flow business than a deal flow business



2017: Transition & Acceleration

2017: Transition & Acceleration

2017 was a year of change for me. I started out the year as Chief Revenue Officer at Choose Energy, culminating a 4.5 year role with the company that began as the first non-engineer in 2012. With the sale of Choose Energy in Q2 and my responsibility with the company melting away, I experienced a brief, but noticeable emotional lull. I had (re)started my dream job, working in venture capital at the intersection of technology and industry with the Invenergy Future Fund but I was missing the action of day to day operations. Working at Choose Energy with world-class employees and a truly unique entrepreneur was special, and the loss of that continuous engagement affected me. I hope to work with each of them again in some way during my career or personal efforts.

And just when there was a lull in my usual intensity, my new team at the Invenergy Future Fund of Michael, Amy, Juan and Carmeanna got me revved up for the truly unique opportunity we had ahead of us. We are now in the early stages of executing our plan to be a world-class venture firm focused on software companies in the energy & industrial verticals, and the machine is really starting to hum. I am increasingly confident in our unique value add as operators, industry connectors and EQ-aware professionals. The combination will take years to prove out but I like our foundation.

Part of our Fund’s momentum includes two new investments we made in the second half of the year. While the investments have not been formally announced, I can’t wait to share more about each of them. The management teams at both companies are elite, focused on driving industry improvements through products that are already operating in the broader industrial environment. The executives and the problems they are solving motivate me every day to find ways to be helpful to their existing operations and find more companies of equal excellence.

2017 also marked my first full year back in Chicago. Being closer to family is everything I hoped for, and more. The family connectivity, coupled with my amazing wife enables a balanced approach to personal and professional growth.

Overall, 2017 was a blessing both for the end of one personal chapter as well as the beginning and acceleration of another. I’m thankful for those around me and excited to work with my expanding team and network to enable and support continued success.

Joining the Invenergy Future Fund

Joining the Invenergy Future Fund

This post is a bit late but with the whirlwind first few quarters behind me, I finally had time to reflect on joining the Invenergy Future Fund. We had our first close in May and the team has been going full steam since 2016…

When I review potential venture investments, I look for a special team with leading & complementary industry experience that is targeting a big market by addressing a specific, impactful problem. Using those parameters, the Invenergy Future Fund was a personal investment that was too good to pass up.

What is the Future Fund?

The Future Fund is a recently launched venture capital firm focused on making early stage investments in technology companies that address the application layer of the energy & industrial verticals. Our belief is that significant existing and ongoing investments in distributed and modern energy infrastructure enable and require a new host of businesses to maximize, control and secure these assets. These software solutions will be capital light, require domain expertise, and will also be scalable from energy into other industrial verticals. I am especially excited because while our focus is targeting a specific area where the Venn diagram of software & energy overlap,  businesses that succeed in our spectrum will achieve success in other areas of the industrial vertical.

Who are the People?

Succeeding in venture capital in the energy & industrials verticals is not easy. You need experience as an investor through multiple cycles, operating experience, and a deep industry appreciation. With Amy Francetic, Juan Muldoon and myself I humbly believe we have a strong core to execute our plan. Amy is a rockstar with both energy investing experience through the CET and operating experience in high growth technology companies and I am excited to learn from her. Juan – who first found me late last summer- is brilliant, and tireless and has a special way of digging into key company drivers… and risks.  Cameanna Eberly is also a core asset to our team keeping the ship running smoothly. And, alongside us we are fortunate to have Michael Polsky (CEO, Founder of Invenergy) and Jim Murphy (President of Invenergy) to guide us and ensure we see the forest through the trees. I was lucky to have Michael as an investor in Choose Energy and know that his perspectives on the future tend to be accurate. Finally, our team is lucky to have access to Invenergy resources and engineers and operators to help us evaluate and understand opportunities in the increasingly high pace energy and industrials environment. The people and our close resources are undoubtedly are the greatest edge.

What’s next?
We have made one investment in Aquilon Inc. and are continuing to review investment opportunities. If you know of early stage companies with software solutions that have an application in the energy and industrial verticals, please let me know. My email is or you can find me on Twitter @JohnJTough


VC Operating experience 

VC Operating experience 

I like to joke that if I could, I might just go back to a younger “me” and punch him in the face.

I had a dream job as an associate at Kleiner Perkins. I was working at a storied firm, had access to world class mentors and investors, and had premier investment opportunities literally walking through the door.

One of the main problems I faced? Saying no. Saying no in venture capital is hard. I saw hopeful, brilliant and dedicated individuals dedicating their lives efforts to potentially transformative ideas. And as a VC, you have to say no to most individuals and companies you meet with. But saying no when I had not been on the other side of the table as an operator myself felt disingenuous. I was giving advice to entrepreneurs, and passing on investments, without having my own personal start-up peaks and troughs. In the words of Teddy Roosevelt, “the credit belongs to the man actually in the arena”. And while I was respectful to each entrepreneur, I believed that to give better feedback and to better earn the entrepreneur’s confidence, trust, and counsel, I too needed to have my own experience(s) in the arena.

There is an ongoing debate about whether you need operating experience to be a great VC. There is no correct answer to that question. What I do know is that I personally needed the start-up experience. I felt I needed to earn the entrepreneur’s respect and that my advice and feedback would carry more weight if the start-up management team knew I had been in their shoes. I want my entrepreneurs to know that I have experienced those growth problems… been told no before (many times) and have personally felt the rush of success and the dreary despair of failure.

And now, with over 5 years of experiencing managing the growth of a start-up I am both proud of and humbled by the lessons I learned along the way.  I’m thrilled to deliver those lessons (and new ones!) to the firms I will meet with and invest in going forward.

5 M&A Insights from the Choose Energy sale

5 M&A Insights from the Choose Energy sale

As I wrote about last week, Choose Energy was sold earlier this year. Beginning in 2015, Choose Energy had multiple casual M&A discussions. But, we did not formally engage until we knew we were ready as a company.

With a few months delay giving me a bit of clarity, I wanted to share some advice / insights that stand out to me about the process and how to prepare for our own deal:

  1. M&A is hard. Very, very hard. Finding the right buyer, at the right price at the perfect time in their strategic initiative game plan is rare. Choose was lucky in that the company had inbound interest. And even then, not easy. (Jason Lemkin at SAASTR has documented just how hard this can be for companies with ARR type revenue and how they should aim to sell at local maximums.)
  2. A clear internal deal champion at the acquirer is required. And you need that individual and their team to have a clear path to continued success after the deal.
  3. Deal fatigue is real. – for both sides. I have raised Series B & Series C capital from a combination of strategic and VCs. Those processes are time consuming. M&A is double or triple that. Have a great team in place, hire great advisors and have an experienced CFO. (We were lucky to have David Yi, a serial KPCB CFO) The amount of work is unexpected, even for someone like me that expected it. To get through it you really do need to create a bond with the acquiring team and “gang up” on the advisers. Part of their job is to be fall guy so the buyer & seller can rally around a common enemy 🙂
  4. Be prepared for regulatory requirements. For companies in the energy & industrials space that capture proprietary data and engage with federal and state level regulatory bodies, be prepared! Good process as you grow the company saves you from some major headaches down the line as lawyers dig through diligence and process documentation. Again, hire a great CFO, even part-time.
  5. Enjoy the ride. There is something very odd about the completion of a sale. You go from being independent and controlling the asset to suddenly having a disbanded board and an entirely new organization structure, reporting structure and incentive structure. Even if your acquirer provides barely any oversight post acquisition, there is still a mental change. For me, this was one of the oddest feelings… and I liked our acquiring team! Enjoy those last few months of corporate independence.

Once a deal is complete there is an entirely new set of issues to address around corporate communications for employees, customers, service providers, and regulatory agencies. I will write about that experience in the coming weeks.

If you enjoy this, please share!

Choose Energy is acquired, hat tip to Jerry Dyess

Choose Energy is acquired, hat tip to Jerry Dyess

Last month Choose Energy was sold to RedVentures.

I joined Choose Energy as the Director of BD in June 2012 in coordination with the Series A investment from Kleiner Perkins. I was the third employee and first non-engineer. The range of highs and lows we experienced as we grew the company from under half a million in annual revenue to over $10M in ARR were dramatic. There were many unique components to the CE growth that I am look forward to diving into over the next few months. But now that the deal is done and public and was successful from both a financial and educational perspective, there is one major thank you I need to give:

Thanks you, Jerry. Jerry Dyess is the Founder & CEO of Choose Energy. At first glance Jerry doesn’t “match” the Silicon Valley CEO fit. And frankly, early on in his tenure at Choose, he didn’t. Based in Plano, Texas with Louisiana heritage Jerry (admittedly) never felt totally comfortable in a San Francisco board room. Instead of board discussions he preferred customer conversations, employee engagement and products that drove immediate revenue and feedback. Jerry never explicitly stated this but if I had to summarize four of his main mantras, they would be:

  1. A small company grows into a big company through many small steps
  2. Revenue follows value provided. (A relationship that many SV firms tend to believe is the inverse)
  3. Hire the best people and get out of their way
  4. Stay lean. Excess cash causes problems. See point 1!

With the deal now in the rear-view mirror, what I am most proud about and thankful for is working with Jerry from the first days after the Series A to final day of the sale. Jerry is the consummate entrepreneur and I have no doubt that the ultimate success of Choose Energy was driven primarily by his product vision, his employee and customer empathy, and his market understanding. He transformed as a leader and I am proud to say I worked alongside him as his Chief Revenue Officer in our final year. In today’s transient workforce, I would like to believe that our enduring run at Choose Energy was pretty special.

And I can’t wait to see what he does next.

getting into venture

getting into venture

Fall 2010

August– Met with Professor Ellen Rudnick about different initiatives at Chicago Booth to promote venture and entrepreneurship. She introduced me to the Chicago Innovation team leaders. Met with the senior leaders there and quickly realized the program was significant more scientific than business model & scaling, where I wanted to focus.

August- Found a way to reach out to nearly every second year student that had some VC exposure and even some recent graduates

September- Met with (now former!) Professor Linda Darragh, who was launching the Impact Investing Summit in Chicago. She was looking to find companies that had both economic and social returns to present to a group of social impact investors. Met and reviewed 20+ companies over 2-3 months and then prepared them for “demo day”. My first real venture and early stage advisory experience. What a THRILL!

November- Applied to Hyde Park Angels and got very lucky to get in in the final spot. During that time it was still run by Ira Weiss (now leading Hyde Park Venture Partners!) and Sam Guren (epic venture investor!). Within months was the head associate for the business services vertical and we were reviewing businesses, meeting with entrepreneurs and analyzing multiple deals every week. Truly an amazing experience that shows an early VC the importance the requirements of vision, analytics, compassion and interpersonal requirements within the VC space.

Silicon Valley Exposure

December- Selected to participate in the Chicago Booth west coast VC trek. This opened my eyes. It was only 3-4 days but it was a magical trip. We met with a dozen venture and start-up firms over 3 days and got an abbreviated insight into the world of VC across multiple different industries and stages of focus. I was beyond hooked… I almost instantly confirmed all my intentions, and knew it was where I wanted to dedicate my career. The combinations of audacious ideas, big bets, the criticality of leadership and teamwork… I loved it.

Day 1: We met with three venture firms and two start-ups….. AirBnB (a month after they closed their Series A) and Optimizely (still pre-seed investment). We were all too focused on the Battery Ventures meeting later in the day to pay attention to the two leaders of these companies trying to tell us to drop out of b-school and join them. Whoops

Day 2: We met with 3-4 more venture firms. One that stood out was Charles Tai from Charles River Associates. He mentioned this report called the “PWC Moneytree Report” and said it listed all the venture firms. I took a mental note. My unstructured and competitive senses simultaneously told me that list was my gameplan.

Day 3: More VC firm meetings. The general theme was “give before you get” and find way to be proactively providing value to the entrepreneurial ecosystem and good things will happen. In a separate meeting another VC told us about how one of his “spray and prey” investments made visual word clouds. Terrible business? Likely. Great way to summarize the data gathering of the trip? Absolutely.

And so, I took my 10+ pages of notes and brought the keywords into the software…and boom… suddenly I had a soft, visually-engaging content way to introduce myself to everyone on the PWC Moneytree Report. Just an icebreaker. And here it is.

January 2011: Reach out to about 80 firms on the PWC 100 list. Found 1-2 partners at each firm where I could make some interpersonal connection. Here are some stats, as I tracked everything in a funnel, like a sales process! (I will be expanding on each stage with some incremental posts but this is the skeleton structure)

Outbounds or Introductions: 110+

Each inbound was light and easy and tried to have a basic connection with the VC based on either their investments overlap in my sector interest or some overlap in their personal interests that were listed on their site or public profiles (Twitter, blogs). I would state my case that I wanted to enter VC and recognized the need to get involved and provide value over the next 24 months of school. I essentially was shopping free help.

It has been well-documented how VCs like to have a set of longitudinal data on an individual for consideration to join the investment team. Mark Suster talks about this with his hires. He needs to see multiple years of data points and experiences to understand the candidate’s performance over time and their general responsiveness to all types of life issues. I couldn’t agree more with the importance of following an “individual’s trend”. Consider these outbounds as merely day 1 of a multi-year process to a formal job in VC. Having an online presence helps share some of your earlier data points, so continue to contribute your interests and general thought processes and action items, when applicable.

Reply engagements & communications: 70

There is conventional wisdom that most VC firms do not hire associates or interns. Many of my initial feedback emails from VCs were quick notes saying as such. But, maintaining a cheery attitude and willingness despite there being no job at the end of the experience is still a great way to keep the conversation flowing. In fact, both places that I ultimately received a job offer from had never had an associate before.

In these meetings I would indicate my area of focus and how I believed my sector interests, perspectives, and growing network (and huste!!) would be a complementary value to the VC firm. And with that background I would offer to be helpful in ANY way. I would always prepare (an hour + for each call) about the person and their investments. I would come with an idea to provide value to them and a specific portfolio company or two. And would always offer to do more for a potential next call.

One of the biggest surprises here was who responded. Very big name VCs would engage or pass me along to a partner in the fund after a few sentences appreciating the word cloud. Amidst all of the “we are not hiring” emails or non-responses seeing how very senior and reputable VCs treated me well when they didn’t know me yet was a nice touch of class and inspiration.

If I was paying it forward they were paying it backward.

Follow-up meetings (in-person or with more materials): 25

These were some pretty in-depth meetings where I would do whatever I had previously offered and then a boatload more. I was of the mindset that I was a free agent and with every meeting I was leveraging prior meeting intelligence gathered around industry terms and market trends. And with that positive feedback loop my conversations became increasing substantive and resulted in a number of referrals.

For any of these meetings I would say “happy to chat over the phone, or I will be in the SF area next Thursday” and if the VC agreed to meet in person, I would buy a flight that day and try to convince a few others to meet in person at the same time.

Take a meeting with everyone. Your goal is to get smarter with every meeting and to ultimately create a mini echo chamber so that in the off chance two VCs you have spoken with know each other (it is a small world in VC)  you can reference your communal relationship and begin to establish more credibility. And, if you are really providing value to these individuals, that positive contribution will be recognized and communicated as a method of thanks. Again, do this work even if there is not a job at the end of the tunnel with a specific firm. At worst, your learn and gain experience and gain a bigger network!

It was exhausting but a real thrill.

On-site broad partner “discussions” (interviews): 4 

They are never really called interviews but more exposure to other partners in the Fund to see compatibility. In general my approach here was ALWAYS to provide value and assume that they were busy and could look to me to be a mainly independent asset to supplement their work and go target and find industries that they were not fully into yet.

For my interview with the KPCB team I proactively analyzed two to three big industry trends and used an investing framework I was learning in school and from my ongoing meetings. I used those frameworks to assess the industry trends, identify where the best companies would be positioned and went and found a few of them. The goal was to show I already knew what the job was… even though I was (in retrospect) really oblivious.

Job offers: 2!

Both came in March of 2011 so it was a full speed initiative for those four months. And then the real work began!

lessons from business school

lessons from business school

Lessons from business school

I am doing this with a few years separation so I am sure I am missing some of the intricacies but that should also help keep this more directional. A few background notes:

– I lived in Chicago prior to school, and therefore didn’t live in the “dorms” where many students end up living
– I didn’t go after a traditional on-campus recruiting job
– I prefer to have 1:1 or 1:few in-person meetings versus mass get-togethers and do my best thinking after listening for a while and going off on my own to process and formalize my thought process. I generally hate big room gatherings and the idea of clusters of people

With that, here are my lessons

1) Know your strengths and weaknesses and put yourself in a position to succeed on the job search front. This will mean saying no to many, many things and being patient as many others around you converge towards the latest on-campus event. There will always be something to do and somewhere to be and if you expend your energy in distracting areas, you will naturally reduce your ability to focus on the path of your main target.

2) Expand your reach socially. It is unlikely you will ever be in a place where you will have such an expansive set of stories and experiences from people who have absolutely no similarities to you. Get curious and, if possible, form working groups outside of your comfort zone. Look for social events that are new to you and go on a few trips to different parts of the world with people from the area. Learn from a local – it will make the experience more rewarding. These relationships will help develop your breadth of thought as well as your empathy and fascination towards initially foreign cultures. You will learn new questions to ask and new ways to approach problems and develop solutions.

3) Make friends with the faculty and engage them to uncover their experiences and motivations. Many students forget that our professors are more than just teachers. They have their own careers, their own stories and their own aspirations. This isn’t undergrad – you are more of an adult now and if you can connect with a professor as a professional and not just a teacher, the experience will expand your learning experience dramatically. But don’t do this for the grades – do this if you have genuine curiosity in their story. Professors see hundreds of students a year – they have great BS meters. Any fake intentions will be discovered immediately.

4) Take the best classes you can as early as possible in your 2 year stint. This way you will get access to the best professors early on (see part 3) and you will take those learnings and bring them to other classes within the curriculum and your job search outside of the curriculum. And do well in those classes. In general, this is one of the great parts of Chicago Booth- a supremely flexible curriculum that you can develop to your own aspirations.

5) Forget the hierarchy of first and second year. Everyone is there as a student looking to better themselves. Treat everyone the same: with respect, and continue to give forward any advice you have obtained. The higher your network (friends, school) reaches, the higher you will reach. Give even when there isn’t a certainty of reciprocation. And, this holds true beyond the walls of your b-school: engage with the community and if you are lucky, with other business school students at other schools. Your career is young and paths tend to cross un the unlikeliest of ways.

6) Use your spare time to improve yourself outside of the classroom as well! You wont have two years this “free” for a while… so tackle a new sport, get a pet, try an instrument, learn a new language or cooking technique. Whatever it is, just surprise yourself and go with it.

why business school

why business school

To most aspiring MBAs, the tradition two year program offers a “reset button” to lateral into an industry outside of the applicants existing career track. And, depending on the target school’s strengths, the majority of applicants are usually aiming for a role within the services, advisory or direct investments field. When looking at the largest employers for the top 10 schools, similar names emerge: large investment banks, large consulting firms, select consumer goods firms and the occasional technology firm.

Most candidates have heard of the prominence and pay upgrades that these careers offer and give up two years of income and shell out around $125,000 for the right to prepare and pivot into one of these industries. Pause for a moment. That is $125,000 in after tax dollars of cost on top of (likely) a few hundred thousand dollars in lost income. So, around a $300,000 investment. Woah.

Everyone has their own unique reason to go to school. Some are even forced to by their firms.

For me, there were three main reasons:
1) The 2007-2009 crash showed me how isolating being strictly a finance professional can be during times of economic underperformance. And those finance professionals that were not balanced with a hint of operations experience and strong networks were the hardest hit. I saw the MBA as a way to expand upon my strong finance base, while simultaneously expanding my network to people in many verticals with many different areas of interest. I recognized that my network within finance was pretty homogenous and I wanted to expand.

2) I had developed the start-ups and growth bug and loved the fact that superior operating advice and financing structure can yield outsized outcomes when paired with the right teams. I knew I was not founder material – as I had way more interest in the strategic levers of growth and the ways to finance different business models to optimize growth & trajectory while limiting the downside. I realized pretty quickly that the start-up market is woefully inefficient as companies balance growth aspirations and capital requirements and my ability to provide insights into growth efficiency from Seed to a growth round was going to be a sustainable differentiator if I could develop those skills.

3) I dedicate 100% of my time to my current efforts. So while many people can spend half-ass a job while they are transitioning, I just don’t have that in my blood. I knew that two dedicated years to developing my skills and network was going to be way more efficient than doing so part-time or outside of my work hours at meet-ups, etc. Quite simply, I forced myself to create time in my calendar and hit a reset button of sorts. May have been an expensive way to do so, but I recognized my weakness.

And so, I took the GMAT (twice) and applied to a couple of schools. I got into Chicago, off the waitlist (woohoo! – found out on the tennis court in Florida, that was nice 🙂 )and from that moment on I started officially expanding upon my career plan that I had detailed in my application essay: to get into the venture industry.

biology to finance

biology to finance

When I graduated from Duke University I proclaimed to myself that I had taken my last exam. No more studying, ever. And with a degree in Biology and Chemistry, I was making the very logical next step to enter investment banking. It was 2007, finance was still (momentarily) the rage, and ethanol was still slightly the rage and between some midwest connections and the tiniest of Venn diagram overlap between ethanol and my life sciences degrees, UBS Investment Bank deemed I was one of the right candidates for their largest analyst class, ever. In retrospect, that should have been a pretty good indicator to the top of the market / finance bubble. There were not even enough training desks for all of the analysts!

Thankfully by the time I actually got to the Chicago office most of the ethanol deals had gone the way of history and I focused on a mix of M&A and midwest coverage- getting the full spectrum of balance sheet and M&A strategy exposure. At first though, I totally fell on my face. My non-finance background proved a difficult transition into making M&A models, as my other classmates with more of a finance background raced ahead. I likely finished near the back end of my class my first year as an analyst and that was a difficult pill to swallow. But, over the course of that first year I had recognized my deficiencies and sought out some senior associates and directors to provide more direction: I admitted I needed to learn, and hunkered down.

And so, by my 14th month, my skill-level was growing at a near-vertical pace and I was the lead analytical resource in the midst of a 4 month M&A transaction working alongside one of those mentors. The deal had me in the office literally everyday for about 15-18 hours a day – with my curiosity, drive and fellow cubemates all helping me to get better. The hours were tough but it was a forming experience that ultimately earned me respect and a few more deals to learn from before my two years were up. The entire experience of growing professionally whilst outlasting every round of layoffs was a lesson I will never forget and I have some great mentors, friends (and a few grey hairs) to keep those lessons forefront.

And so, when I was looking at what to do next after my two years at UBS, two of the leading Managing Directors in the office went to bat for me and directed me to the XMS Capital team.

With XMS’ much more personal approach to advisory and (at times, co-investing) I was able to experience much greater alignment with the companies – and see to an even greater extent how the combination of relationships and hard word really do drive outsized returns for all parties. I was hooked. I was able to work across many industries: energy, technology, healthcare, retail (i even worked on starting up a music colliseum and surrounding mall). It was a great group of senior leadership at XMS that allowed their junior team to expand their scope – and I credit a lot of my fundamental business model learnings to them allowing junior staff to do much more analysis and engagement with the companies. Combining that enhanced engagement with access to those same leaders (at XMS and at the companies) to answer my myriad of questions and I really was getting a lesson in finance, strategy and growth execution.

And so, with only a year under my belt at XMS I thought I may stay forever but I had a nagging hunch that I needed to solve. More on that and why I chose to go to b-school next.