Diving In: What You Can Expect in the Investment Process

Originally posted in 2018, this blog has been updated as of March 2022 to reflect Laconia’s current investment focus, strategy, and process. If you remember reading something different before, you’re (probably) not hallucinating! For additional resources, you can check out our FAQ, sign up for an office hours session with our investment team, or submit your information for funding consideration.

This is part 4 of a 5-part series. If you haven’t done so already, you can read the first three posts here, here, and here.

Navigating the fundraising process is often one of the most frustrating parts of running a startup. It can be slow, opaque, misleading, and even contentious. We at Laconia do everything we can to make the experience not just relatively painless but also productive for founders. Regardless of the final investment decision, we hope each of the founders diving in with us take away something useful from the work itself.

VCs are not all the same, so what you see below may or may not apply to any other firms. The short story is that we focus on operations, leverage our community, and build a strong partnership over the course of the process. In more detail, here’s what you can expect from us:

Discovery

After reviewing some information about a company (e.g., their website, a pitch deck, a short blurb), we often decide to take a first meeting to determine whether this opportunity is a mutual fit. Because our investment team is so small, we each take intro calls individually. After this first call, we may follow up with additional questions via email or discuss the opportunity internally. If we decide to move forward, by the second or third meeting, you will generally have met our whole investment team (David, Jeffrey, Geri, and Reena; interns, too, if they are around).

Here are the questions we aim to answer in these discovery sessions:

  • Does your company fit our investment thesis in terms of stage, geography, and sector focus? More on our focus in blog #2. As a side note, occasionally we meet impressive founders who, for whatever reason, do not quite fit our investment scope. In those cases, we are happy to make introductions to VC friends and colleagues who may be a better fit.

  • Are we aligned on the big vision and upside opportunity? We can’t always answer this question fully in just a meeting or two, but directionally, we need to share a vision of where a certain market or industry is going, as well as a shared belief that this business is a venture-scale opportunity.

  • Do we bring value beside capital to the table? We only make 4-8 investments per year and work very closely with entrepreneurs, particularly in the first 12-18 months post-investment. We want to make sure that there is alignment between what you need and what we can offer at your current stage.

  • Do we get along? Investing is a long-haul relationship, so we have to be able to work together.

Due diligence

If we are all in agreement that the answers to the above are “yes”, we will move into our formal due diligence process. Typically, we can reach an investment decision with a few weeks. The extent of our diligence varies somewhat depending on the stage of the company, as some items that are critical to a post-revenue company raising a $4M seed round may not be relevant at all to a pre-seed startup raising $500k. Below is a detailed breakdown of the items we consider internally while conducting due diligence:

  • Stage 1 is centered on the operations of your business & your thinking around it. Across 1-2 working sessions, we will cover the following:

    • Financial statements (historical & projected)

      • This part is fairly standard: revenues (especially monthly recurring), costs, margins, growth assumptions, revenue concentration, and so on. Having an intuitive and easy-to-follow model always helps.

    • Sales, marketing, and distribution

      • Sales & marketing strategy as a lever for revenue acceleration

        • We dive into all of the assumptions surrounding your sales process to determine what actually drives your numbers. We go into these meetings with the understanding that you know your business best and that we are here to offer insight and suggestions based on our vantage point. A sample of questions is below:

          • How are you segmenting and prioritizing your customers?

            • How do you define product/market fit?

            • What are the components of your sales cycle, and what drives results at various stages of your sales funnel?

            • Is your pricing model right?

            • How is your sales team structured?

            • What will enable you to go from x% to y% market share?

            • How can you meaningfully and efficiently scale your sales efforts?

      • Market size with supporting market research

        • True market size numbers are hard to come by. We are not looking for a top-down data point for “total IT spend in X industry”. Segment your market fully and calculate every sales dollar you could feasibly close based on total number of potential customers and total revenue you could generate. Do this both for your current products as well as for future product development/market opportunities. In conducting this analysis, we are looking both for downside protection with regard to your current in-market product as well as the “big vision” that funding and growth would enable.

    • Competition

      • Clearly map out your market position and unique value proposition relative to your competition. We often find that competitive sets are not fully identified.

    • Capital structure: cap table, copies of convertible notes, debt, etc.

      • Far too often, we meet founders with multiple layers of stacked notes and limited understanding of everyone’s true stake. We will work with you on cleaning up your cap table, understanding the founders’ ownership, adjusting the option pool, and conducting scenario analysis for current/future rounds. Our top priorities are ensuring that founders are probably incentivized & that the company is as attractive as possible for future investors.

      • This topic includes discussion of current round terms. Are you raising the right amount based on your operating plan? What are the milestones you need to reach to trigger your next financing event? Does the valuation you want make sense given the stage of your company, and how does it align with your projected growth trajectory? (More on capital strategy here).

  • Stage 2: Once we have gotten comfortable with the above, we will start including others into the process as well. We will reach out to our LP base, comprised predominantly of family offices and high net worth individuals, to leverage their expertise and networks. We almost always get 3-5 responses with potential customer introductions that simultaneously give us real market insight and provide you with sales leads. While conducting these calls, we will make a few more document requests on:

    • Customer information: top customers, churned customers, etc.

    • Product development: roadmap, development costs, execution risks

    • Management

    • References: customers, existing investors, potential target co-investors

      • We will hold off on calling any of your customers until the very end. Toward the end of this second stage, we will begin putting together the investment syndicate. We do not invest as the sole institutional VC.

  • Stage 3: This is the home stretch! The final items are tech due diligence, customer reference calls, and some more checklist documents.

    • Tech due diligence: infrastructure, tech stack, security, tools, etc.

      • For each tech due diligence call, we bring in one of our portfolio CTOs to lead. This approach allows us to leverage their expertise and also introduce founding teams to each other, which is key to the Laconia community we are building. As our focus is on applications of technology for high pain-point B2B problems, we often are not taking on significant risk with cutting-edge technology.

    • Terms & investor syndicate

      • The timing varies a bit case by case, but typically we will formally issue a term sheet post tech due diligence. We prefer leading, and we are open to co-leading or following if that makes the most sense for a given company. If we have not yet finalized the investor group, we will focus all of our efforts on that now.

    • Reference calls: senior executive team & customer reference calls

    • Legal & tax documents: trademarks, litigation, tax returns, incorporation docs, etc.

While this may all seem overwhelming on paper, it is a highly collaborative and engaging process. The most important parts for us are deeply getting to know founders and building lasting relationships with them and the co-investors in the round. We can make an investment decision in as little as a few weeks, but seeing founders execute and showing them the way we work are critical to setting a strong relationship foundation. Most of all, we enjoy rolling our sleeves up with founders and leveraging the growing Laconia community. 

Some final tips on managing your investment process if you are still awake:

  • Create a target VC list that makes sense for your company. Make sure a VC’s fund size makes sense for the company you are building (e.g. a $10B fund will have no interest in a company aiming for a $100 million M&A exit) and that its investment velocity aligns with what you need (e.g. a fund that writes 2-3 checks per week will not be providing the deep dives and hands-on support described above).

  • Prepare a deal room with your deck & the docs listed above prior to beginning your fundraising process.

  • Treat fundraising as a sales process. Identify your prospects, move them through the funnel, and close them.

  • Do your diligence, too. Call a VC’s existing portfolio founders and find out what they do, not only when things are going well but especially when they are not.

The next & final blog in this series will be on what it’s like to be in the Laconia family. What can you expect from our onboarding, community, and ongoing support? Keep an eye out. In the meantime, let us know if you have any feedback here or on Twitter — @jsilverman22, @djarcara, @geri_kirilova, @JailwalaReena.

Saying Hello & Goodbye: Laconia's Internship Program

Saying goodbye to a family member or friend as they move forward in their life is always a bittersweet moment. It is that time of year at Laconia when we must say goodbye and thank you to our latest team of interns.

We run a paid part-time intern year-round, either for an academic semester, a full academic year, or a summer season. Our internship program has been widely successful, attracting talented students from NYUColumbiaCornellPennBrownUMich, and Rutgers, among others. In addition to intellectual curiosity, exceptional work ethic, and adaptable skills, they have all brought to the table a genuine passion for technology, entrepreneurship, and venture capital investing. Numerous former interns have gone on to pursue full-time opportunities at other venture capital firms and Laconia portfolio companies, with one former intern even re-joining Laconia full-time. Our interns are among the firm’s strongest ambassadors, often referring future candidates and budding entrepreneurs.

Our program fully immerses the interns in the inner workings of a venture capital firm, providing extensive first-hand exposure to all aspects of the work required. In preparation for the program, they read Ventures Deals by Brad Feld & Jason Mendelson, review Laconia’s Private Placement Memorandum, and become familiar with our portfolio companies. While with us, they are involved in deal flow & sourcing, due diligence, portfolio support, industry research projects, marketing, and operational support. We treat our interns as associates, and, in return, we get hardworking, smart thinking, and creative minds who allow our small team to accomplish so much.

We are strong believers in compensating them for their work along with providing them with a platform to learn, grow, and explore. Internship programs are great vehicles to allow young adults to dip a toe in the real world so they better understand the direction they want to take and the skill they need to develop. Payment extends access rather than limiting the field to only those who can afford to work for free.

I end this by saying goodbye to Jodie Miller and Ravi Shah and wish them all the best as they graduate and head off to PwC Strategy& and IA Capital respectively. They were stars and will be sorely missed. The good news is that as one door closes, another opens, and, with that, we welcome Naomi Grossman and Addison Huneycutt to the Laconia family - we can’t wait to see what you will create here!

Legal Tech Industry Landscape

One of our fabulous associate interns, Jodie Miller, put together an extensive report on the legal tech industry landscape - please check it out below. We hope this document can serve as a resource for future deeper dives and due diligence sessions on companies in the legal tech space. This project is a work in progress, and we hope it can be a useful starting part for anyone who comes across it. We look forward to hearing everyone's feedback and additions.

Moving Forward and Beyond: Our Statement on Diversity, Inclusion, and Anti-Harassment

The business case for supporting diverse teams is cut and dried. This blog is not the place for a recap of the comprehensive and compelling data on the topic. Instead, we want to move the conversation forward from “Why?” to “Here’s how.”

The past year, and especially the past month since International Women’s Day, has exploded with new voices, organizations, and initiatives for moving the tech and venture industries forward. It has sparked conversation and, more importantly, action, not just in the broader community but also in our own tight-knit office at Laconia.

When I received an offer to join Laconia full-time about a year and a half ago, I was ecstatic. Having entered the VC world at age 19, I had already learned the hard way how important it is to work with advocates and allies. My decision to join Laconia full-time was solidified in no small part by Jeffrey’s & David’s demonstrated commitments to transparency, inclusiveness, and empowerment.

This topic is deeply important to me, and I personally vouch for our whole team’s commitment to going to bat for underrepresented founders and to doing what is right. We will inevitably make mistakes. We will listen, learn, and improve.

Pushed by the #MovingForward initiative to articulate this commitment, we are publishing our official policy on diversity, inclusion, and anti-harassment. Part of me can’t believe that most of this has to be said, but here it is, loud and clear:

Laconia is committed to building a safe, transparent, and collaborative environment for our entire community, including but not limited to entrepreneurs, employees, interns, Limited Partners, vendors, and other ecosystem partners. Diversity, inclusivity, and transparency will remain core to our business and the community we are building.

We believe that investing in diverse and ethical teams leads to better decisions, outcomes, and returns. We are committed to increasing our investments in underrepresented founders, who comprise 23% of our portfolio to date (as of 4/2018). We will not back founders who have been found to engage in discrimination, sexual misconduct, or sexual harassment.

We have zero tolerance for harassment, discrimination, or retaliation of any kind with regard to anyone in our business network, including founders, investors, co-investors, vendors, and, of course, our own team members. We will appropriately and confidentially investigate reported misconduct of any kind. Any incidence can be reported to any member of our team.

We will continue finding the best ways to support, encourage, and engage entrepreneurs to build a more representative, safe, and inclusive community. We are adding the VC Inclusion Clause to all future term sheets and continuing conversations with existing portfolio companies regarding their diverse hiring goals.

Beyond our internal teams and portfolio companies, we are extending our diversity goals to our vendors as well. We are making it clear that team composition is a component of our evaluation criteria for vendors and partners, encouraging company-wide diverse representation and working toward ecosystem-wide progress.

Below are a handful of our active initiatives to expand access to the venture network to those who may not be connected to us already through traditional channels:

  • Mentor Meetings: Any founder can sign up on our website to come meet with us for 30 minutes to ask any and all questions about raising capital and building their business. No warm intro or context needed; just sign up, show up, and share with other founders.

  • Office Hours and Partnerships: Same idea as the above, except we come to you at your co-working space/incubator. Please reach out if we’re missing your space.

  • Mentorship through organizations focused on underrepresented founders such as Monarq. Please reach out if you are part of an organization that could benefit from our time.

  • We run an intensive, immersive, and mentorship-driven undergraduate internship program, training a pipeline of next-generation investors and entrepreneurs. 80% of our interns have been of diverse backgrounds. (Yes, we evaluate cold inquiries.)

  • It might take us a while, but we do our absolute best to answer all cold inbound emails (blatant spam/mass mailings not included).

Lastly, this post would be incomplete if we did not highlight some of the many initiatives and resources that have made us exponentially more thoughtful about our processes & have pushed us to be more vocal about our goals:

We look forward to continuing this discussion about the role that diversity plays in venture capital, tech, and society more broadly to build a fairer and more productive world.

Who You Are: The Entrepreneurs We Seek

Originally posted in 2018, this blog has been updated as of March 2022 to reflect Laconia’s current investment focus, strategy, and process. If you remember reading something different before, you’re (probably) not hallucinating! For additional resources, you can check out our FAQ, sign up for an office hours session with our investment team, or submit your information for funding consideration.

This is part 3 of a 5-part series. If you haven’t done so already, you can read the first two posts here and here.

The more our portfolio grows, the more convinced we become that in the early stages of a company, the founders are most of the bet. We consider our portfolio an extension of our core values of transparency, collaboration, and community. So, when evaluating potential investment opportunities, we benchmark the founders against our existing portfolio entrepreneurs.

While there is no “one size fits all”, we’ve found certain commonalities in successful founders. Below are the core characteristics we search for:

  • Deep business acumen & attention to detail: We love when founders know the key numbers of their business without having to check spreadsheets or reference materials. This attentiveness demonstrates a strong grasp on their business. At the pre-Series A stages, it’s crucial for the CEO to understand all functional divisions, especially business strategy and how it connects to capital strategy.

  • Sales ability: We have an admitted soft spot for founders with strong sales skills in the early days. Founders aren’t required to have direct sales management experience, but we do expect them to have a deep understanding of customer segments and needs, go-to-market strategy, and customer acquisition models to close initial deals and begin the iteration process around determining eventual sales structure. If the founders can’t sell, we’re not buying.

  • Transparency & collaboration: In order for our partnership and the Laconia community to work, founders’ core values must align with ours. We search for entrepreneurs who are open to feedback and discussion, don’t hesitate to ask questions, and demonstrate coach-ability, and over-communicate. These characteristics enable us to build strong and lasting relationships. As one example, one founder shared so much with us during due diligence about his father’s role as a trusted advisor to the company that we were curious to meet him ourselves - and we are so glad we did. This openness resulted in a much deeper understanding of the company's history and, ultimately, a stronger partnership.

  • Confidence & focus: We search for founders who are hands-on and heads-down, interested in building a business, not growing their personal brands at the expense of business focus. You most likely will not find any of our founders on a TechCrunch stage. There is no aggrandized ego involved in their process of growing a scalable, sustainable business, just pure drive.

  • Self-awareness: Often in a first meeting, we ask founders, “What keeps you up at night?” In the answers, we look for people who strive to understand their strengths and weaknesses and try to know what they don’t know. One of our founders, for instance, could not have been more direct with us when he told us “I know how to build this business, but raising capital is a whole other ball game.”  We could work with that and help compensate immediately.

  • Integrity: This one is pretty simple. We believe that bad behavior is bad for business. Who you are personally is who you are professionally. The way you treat waiters, receptionists, and VC interns is indicative of the way you treat your vendors, customers, and employees. Honesty and respect are of utmost importance.

  • Diversity: The research that diversity drives stronger business returns is comprehensive, compelling, and central to our investment activity. We track diversity in our pipeline and portfolio (see metrics on our FAQ page), and we actively make ourselves more accessible to founders outside of our existing networks through our office hours, mentorship at incubators and accelerators, and involvement with diversity-focused organizations. This commitment flows down to our companies as well. We are always open to suggestions on how we can better support diverse founders.

At the end of the day, every investment we make is, first and foremost, based upon partnership. Our trust in our founders’ ethos — and their trust in us — is paramount.

Our next two posts will spill the beans on what you can expect from us during the investment process and as part of our portfolio. How do we hold up to our end of the bargain? Stay tuned. In the meantime, let us know if you have any feedback here or on Twitter — @jsilverman22@djarcara@geri_kirilova@JailwalaReena.