We're thrilled to share that our legacy portfolio company, LeagueApps, has concluded a significant financing round led by Accel-KKR. LeagueApps proves the Laconia B2B investment rule: discover an MVP solving a high pain-point workflow problem combined with great founders who embrace a steady customer-focused go-to-market execution; over time tremendous value gets created with an exciting exit. Congratulations to Brian Litvack and Jeremy Goldberg for a tremendous accomplishment and continued success bringing the company to higher heights alongside Accel-KKR.
The Founders of Laconia first invested in LeagueApps in 2011. We were introduced to Brian and Jeremy as “two really good & smart guys passionate about sports”. They set out to alleviate the pain of managing a recreational sports league. Solutions to that point, if they weren’t paper- or Excel-based, were kludgy at best. This was a huge market waiting to be served.
From Laconia’s perspective, LeagueApps was an early indicator that our B2B investment thesis, the digital workflow transition from manual and legacy software, was also untapped. LeagueApps perfectly lined up with the transition that we were seeing across most industries then and now. Despite the rise in popularity of the B2B investment focus, this transition has not abated. Instead, it is further evolving with the rise of new technologies and AI-enabled platforms.
Still, a market insight is only as good as the people who discover it. Brian and Jeremy showed intelligence, adaptability, keen salesmanship, excellent executive ability, and most importantly patience and honest character. This is not hyperbole: these are always the qualities that bring great companies to fruition in our experience. An idea is only as good as the jockey(s), especially when investing at the seed stage. Seeing our Laconia jockeys cross the finish lines could not be more rewarding!
Founder Spotlight: Sumner and Carla Vanderhoof (Propensity)
Meet Sumner Vanderhoof and Carla Vanderhoof, co-founders of Propensity.
Watch as they share their journey of resilience and innovation, turning setbacks into success.
Breaking Into VC: A Guide to Starting a Career in Venture
Intro
Since joining the team at Laconia 12 months ago, people keep asking me, “How did you break into venture”?
Well, as I shared in the previous blog here about why I joined Laconia, a career in venture capital was not something I grew up seeing, and certainly was not an obvious career path straight out of law school.
For more than 10 years before moving into the world of venture capital, I was an operator first. I started my career in capital markets and spent more than 6 years in business development at Thomson Reuters (Finance & Risk) before doing an MBA and moving to the world of venture-backed b2b software startups. I then spent more than 4 years building and scaling startups, and I was fascinated by the pace, impact, and scale venture capital has to offer. Though I enjoyed flying ships while building them, I wanted to transition my career to creating a larger societal and structural impact. Given my background and passion, capital distribution and allocation became my new obsession. I spent the next few years navigating the space of capital movement: moving funds to charitable initiatives @ Founders Pledge, building an investment club for female retail investors @ 51Unicorns, and orchestrating investment opportunities between angel investors and social impact founders @ SeedImpact. Joining a venture fellowship (big love to IncludedVC) pushed me to fully embark on the journey and make my way to a venture capital firm last year.
So if you, like me, know you want a career in venture capital but come from a unique and untraditional background, here is what I did from the moment I became serious about a career in venture capital. This step-by-step plan helped me land where I am, and hopefully, this helps you too!
One note before we start: in this article, I will not be discussing whether VC is for everyone or who should be applying to VC. I will leave the soul searching exercise for you. However, make sure you don’t skip over this part and spend time thinking about why you want a career in VC. Knowing your WHY is not only good practice, but it will help you stand out from the crowd and keep on pressuring this path when things get tough. Like the best founders (who you will one day back), those who have a clear idea of why they are doing what they are doing - why them, why this problem, why now - tend to stand out and succeed.
The path to VC is not easy, and neither is the work itself, so be sure to know whether this is the path for you, and if it is - let’s dive right in!
Which VC am I? Be Strategic and Play to your strengths
Before jumping into the practical steps one can take to increase their chances of getting a job in VC, particularly coming from an “untraditional background”, I want to start with an overview of the different paths one could take starting a career in VC, and how to decide which path is for you.
As you may know, venture capital firms vary by AUM (asset under management), investment stage, investment strategy, team size, and more. Though the lines are getting blurrier these days, there is a difference between the associate role’s job at a large global venture capital firm and that at a boutique one. Some firms invest in software only, some do hardware, some invest in B2C, and some do medical devices. The world is your oyster but if you want to increase your chances of success you want to align your strengths and interests with the firm’s needs.
Understanding your strengths could help determine which investment stage, thesis, and size of the fund might be best for you. Now I know what you are thinking, you might be the “I am not picky” or “I want to keep my options open” type of person, or perhaps you are the “just get me into a VC, I don’t care what they invest in” type of person. That is all fine and dandy, but if this article is about breaking into VC successfully, then understanding the process and focusing on playing to your strengths will increase your chances of success here.
For example, if you are moving from a finance-driven role to VC (like investment banking) consider a firm in growth stages where your financial skills could become very valuable. If you have killer sales skills and access to brilliant founders, consider early-stage investing instead, where financial analysis is not as heavy.
If you are an engineer who did an MBA, you could focus on early-stage deep tech firms. Or if you’re a medical student, you should pursue an early-stage healthcare fund. I am suggesting early stage vs. later stage as I am assuming they are not a banker turned doctor, to now an aspiring VC … but you get my point!
Of course, like any other job, you also want to consider things like the size of the team, the people you’d be working with, etc.
Find yourself on the map and direct your efforts where the chances for success are cleared.
In my case, though I have sharp financial modeling skills (I worked in capital markets, have an MBA with a finance concentration, BA in economics, and 10+ years in fintech), my resume screams sales and network-building much more, so early-stage investing made more sense for me. I also want to invest in the overlooked funders and markets, a chance you get to do more at the earlier stages of investment. In addition, I spent more than 10+ years building and scaling in the b2b SaaS space, so I focused on firms that were focused on business software as an investment strategy, as opposed to those that were very consumer-heavy.
Of course, don’t be too narrow or you will be left with only 1-2 firms that match your criteria (like I did at one point), but have a clear idea of what your ideal firm might look like - it comes across in spades when a candidate is focused on why they want to be a VC, and what they want.
One last note here about job titles: if you like the team, the firm, and the strategy, don’t over-index on your title. Some people ask me, especially those who pivot at a later stage of their career, what title they should ask for. I would stay open-minded here and judge opportunities case by case. At the end of the day, it is not your title but your day-to-day work that counts.
I know where I am going, but how do I get there?
So once you decide on the investment stage, strategy, and firm size, what do you do?
First, a note about expectations. As we all know, job opportunities in venture capital are slim, especially in this current market. The industry is small (by number of jobs), and positions open at different times, so it’s important to keep in mind that on average, the process of landing a role in VC while actively applying could take up to 6-9 months. Make sure you are aware of that timeline before quitting any jobs or as you plan in advance.
Preparation is key - Immerse yourself in VC
The first step to landing a job in VC is doing your homework. Learn everything you can about venture capital. What is it, how does it work, what do investors in your investment stage look for when investing, etc? Read blogs and books, listen to podcasts, and immerse yourself in the companies building, raising, scaling and exiting in the spaces you are applying for. When interviewing you will be asked about companies you are interested in and why, maybe asked to write an investment memo or decision, asked to assess the firm’s existing portfolio companies and suggest companies that match their investment thesis and more, so you need to be prepared. This stage should also help confirm the question we started this article with - is VC for me?
Consider taking a Venture Capital Class/Fellowship. There are many options out there both paid and free. I did IncludedVC, a unique fast-track MBA for aspiring venture capitalists. At Includedvc I got to learn from the top VC talent everything I needed to know, from cap tables, to deal sourcing, to managing a board and more. We even dove into the mechanics of applying and interviewing for VC roles and how to stand out. I also gained valuable hands-on investor experiences such as deal sourcing, investment memo writing, and investment committee pitching in a safe learning environment. Most importantly, I was surrounded by a community of incredibly talented and kind people all trying to change the face of VC. During the interview process these were the friends who jumped on calls to help me prepare for the interview, and today these are people I share deal flow and opportunities with. Fun fact, it is also where I met Geri for the first time and made sure to follow up with her!
Other programs include VC Unleashed, Going VC and, of course, this article will not be complete without a shameless plug for Laconia’s own The Venture Cooperative, the most accessible on-ramp to venture capital. This is where more than 1,000 fellows learn the behind-the-scenes of venture capital as a whole, dive into Laconia’s investment process in particular, and get to see how venture capital works behind the curtain. Oh, and applications are open for our Fall 2024 cohort until September 22, 2024.
For your DIY version, here are some crowd-sourced resources on good podcasts, books and blogs.
Applying for Jobs
Okay - you know what you want and you’ve learned about the space you want to go to - so how do you actually apply? More than any other industry, VC is highly closed off and job opportunities arise mainly from within the VC network (hence the term “breaking in”). This system is flawed and structurally biased, but you need to understand it as knowing how hiring decisions are made in VC will help you navigate the process better.
You’d probably want to divide your time between Publicly listed and Unlisted opportunities.
Publicly Listed Opportunities
Though you may think your next role would likely come from something other than a job post, I made sure I followed and knew about EVERY job post that was opening up. VCs do occasionally make hires from these structured processes, and in any case, these opportunities give you the chance to get acquainted with numerous firms.
To keep track of Publicly listed opportunities make sure you do the following:
Follow Nicole DeTommaso from Harlem Capital. She has a wealth of resources and information about the hiring process, and posts opening positions that land on her desk every Wednesday. Here is a recent post.
Sign up for Newsletters like Startup & VC and John Gannon for their weekly email listing all VC job openings by location
A warm intro where possible is preferred - If you find a job you want to apply to, the same hiring rules apply. Try to find a warm intro where you can.
Don’t have a warm intro? Send it anyway - If you are applying from a nontraditional background, chances are you don’t have the network to be able to just count on that. This is like the “family & friends” round most founders don’t have. So don’t give up and make sure you get help on building a strong CV and Cover letter that tells your story. You might be surprised, but I had interviews from “no warm intro outreach”. Don’t get me wrong, I had many Nos and Black Holes, but at some point, my CV and Cover letter told the story of “why me” correctly, and I was invited to interviews even without knowing anyone at the firm. Don’t miss out on at least putting your name in the hat.
Unlisted Opportunities
In addition to following job openings and applying to publicly listed opportunities, make sure to build a pipeline of firms you want to work for. A lot about breaking into VC is about timing and you want to be proactive about landing the dream job you want. This is the same advice I would give founders: understand the process, figure out your ideal target and hit the pavement.
Create a list of dream companies that match your hiring profile (based on the assessment above).
Map out where you have connections and try to get introductions
If you have no introductions, see where these people are and go meet them - look at what panels they speak on, which events they might be at, and try to meet them
And you know what I will say - if you don’t know them, don’t know anyone who knows them, and they are hiding and not going to ANY networking events, then “cold outreach” them. I played a game with myself to see how many people responded to my cold outreach. The answer: a lot! Do your research, be relevant, polite, and valuable, and ask for a short time to speak.
A good book about the topic is the 20-minute Networking Meeting book. The TLDR is:
Come prepared for the call, give context, introduce yourself, and ask 1-4 well-researched questions, including who else you should be speaking with. Follow this structure and, trust me, one of the following four things will happen:
The best outcome, they are hiring and you’ve impressed them so much that they want to hire you - not likely, but possible.
They are not hiring, but know someone who is hiring and you have impressed them so much they want to introduce you to them.
They are not hiring, but know someone who you should be speaking with. You have impressed them so much they want to introduce you to them.
They are not offering to introduce you to anyone but they mention a person, a place, a program, or an idea you haven’t thought about, and you are one step closer to your destination.
Always follow up (in no more than 24 hours), give something back, and keep them in the loop about your process. Networking is an art, one you should master as a VC, so you might as well start now. Message me if you want a copy of my networking guide.
In the meantime, immerse yourself in the ecosystem and make positive contributions
I struggle with the traditional VC advice of “doing the work before you have the job” as it suggests people need to do free work in order to be considered for VC roles; in reality, we should be pushing VCs to professionalize their hiring process and be more diligent about how they source and evaluate talent.
That said, trying to gain relevant experience (via paid internships or unofficially) will help you operate for the job you want, not the one you’re already in. Consider immersing yourself in the ecosystem and making positive contributions, whether it's helping founders with their pitch decks, making introductions between people who should know each other, attending events, writing blogs about trends you are seeing in the market, collecting useful information and making it accessible, etc. In short, leverage your skills to build your reputation.
By the time I met Geri, Jeff, and David, I was seeing them at events, I introduced them to a couple of founders (one of which made it to their due diligence process) and I was following and interacting with them online, thoughtfully discussing our approaches towards venture investing.
The work I did when I was breaking into VC is not far from the work I am doing today.
If I met a good founder I would think about which investor I met recently that could benefit from meeting this person. Note: I did NOT send a supermarket list of companies I read about in the news - that is not helpful to a VC. I sent only founders I had met personally at pitch competitions or other industry events and was really, really impressed with.
When you discover these opportunities, email the investor you have in mind with a well-researched and crafted email connecting the investor’s investment thesis to the founder and company and asking if they want to be connected. 4 out of 5 of these emails are likely to be a pass, but I would love to get emails back passing but telling me I was on the right track, like “Ah I already know X, we met with them last week” (perfect! I knew you’d like them); “Ahh I really like the founder, but we struggle with the category” (great, identifying strong teams is critical to early stage investing); or “We are already invested in a similar company” (hooray!); and the best one “Yes, would love to meet, pls connect us”.
ALL of these responses are equally good. They all suggest that you are identifying good founders, building venture scale companies and that you understand the investor's investment thesis and focus - the rest is really not up to you!
A final note about starting
Hopefully, this article gave you a framework to best approach the process of breaking into VC, and soon enough you will land your dream job.
When you do, here are a few final tips about starting
1- Don’t forget to stop and celebrate - you have beat the odds! If you can, try and take some time off to rest before you start your job. As much as you are eager to start, you probably worked really hard to get here, and you are likely to work very hard once you start. Try and take some time to re-set and recharge your batteries starting your dream job on the right foot.
2- Work in stealth mode for the first month (thank you Nicole DeTommaso for this tip). As much as you can, try and take the first month to deeply learn your firm, the investment thesis, the ecosystem, and your team. Strategize before the floodgates on inbound pitches and opportunities start to open. Once you officially announce your role at the firm, you will take every call and meeting, so make sure you come prepared.
3- Do a soft launch and thank all the people who have helped and supported you in the process. Email all those investors and founders you met along the process and share your news. They are going to be so happy for you and are likely to be your first champions in your new role!
If you want to read about how I spent my first 100 days at Laconia, feel free to read here.
If you have any follow-up questions please feel free to connect with me on LinkedIn or email me at: mirit@laconiacapitalgroup.com. Good luck!
Note:
The focus of this article was to try and give you a playbook on how to approach the process and how to try and stand out. There are many more resources out there about what to do once you land an interview/already have had some internship opportunities. Nicole has great posts about these Popular Interview Questions and How to prepare for a case study and her famous 10-page presentation that landed her the job.
Contributed by Mirit Lugassi
Portfolio Spotlight: Trestle
We’re thrilled to announce our investment in Trestle alongside Lerer Hippeau, MetaProp, Alumni Ventures, The LegalTech Fund, Redbud VC, and Meridian Ventures (talk about a party!).
We first met co-founder & CEO Victor Zhang in an unusual way: he sent us a cold pitch submission. Standing out in a sea of inbound messages is no easy feat, but his relevant background and clear value proposition were impossible to ignore.
Trestle is the construction industry’s only subcontractor and supplier data centralization and performance management solution. By creating a centralized platform that seamlessly collects and connects key subcontractor and supplier information from internal and external systems, Trestle empowers contractors to choose the right partners, improve project transparency, share real-time feedback about third-party performance on projects, and mitigate risk before it impacts their bottom line.
Prior to Trestle, Victor spent 15 years in the heavy construction industry. He led large estimating and procurement teams on landmark projects nationwide, including a $3.8 billion construction project, the largest in Virginia’s history. Co-founder & CTO Jason Chen designed and developed countless web and application experiences as a software engineer and team lead. Joining forces at Trestle, they are providing modern software solutions for construction, specifically in areas that are deeply complex and often misunderstood by outsiders without direct experience.
If you are interested in learning more, read Trestle’s announcement here and reach out to Victor directly.
Portfolio Spotlight: LiquiDonate
We are excited to announce that we have led a $3.75M seed round for LiquiDonate. Investing alongside us are Uncork Capital, Kapor Capital, Ganas Ventures, MTV Ventures, Graham & Walker, Maccabee Ventures, and more. (Big thank you to Christopher Lee, a Venture Fellow in our Venture Cooperative program, for surfacing this opportunity!)
LiquiDonate is an innovative inventory management software for retailers' $800 billion+ problem with excess inventory. Today, retailers like Williams-Sonoma, Room & Board, Tuft & Needle, and Liquid Death use LiquiDonate to remove their excess inventory (instead of a costly and hassle-ridden liquidation process) from their overfilled warehouses seamlessly. Retailers also can take advantage of Magic Matches, LiquiDonate’s proprietary AI-powered solution to match unsellable customer returns with local organizations instantly, saving retailers at least 50% on their reverse logistics costs. Furthermore, LiquiDonate increases its customers' net revenue by decreasing fraudulent returns. On the demand side, nonprofits worldwide have about $1 trillion in unmet needs on an annual basis and there are $816 billion worth of returns. LiquiDonate’s solution is efficient, economical, and sustainable for all parties.
Prior to starting LiquiDonate, founder & CEO Disney Petit was an early employee at Postmates where she launched its first five markets and its sales team, signed its first 500 restaurants, and started its first three social impact verticals. Disney has the expertise, vision, and heart to build LiquiDonate into a category-defining company, and we can’t wait for this next stage of the journey.
If you are a retailer interested in seamlessly and sustainability managing returns and inventory, get in touch with Disney to learn more.
Learn more in Axios’ exclusive announcement here.