Portfolio Spotlight: Paloma

We couldn’t be more excited to announce our newest investment: Paloma!

Paloma powers commerce on messaging channels, helping brands get >2x higher conversion rates with automated conversational shopping.

When I first met Paloma’s founder & CEO, Kelsey Hunter, I put all my cards on the table: “We’ve struggled with the e-commerce messaging space in the past because it is so crowded and the incumbent platforms have tremendous market leverage. I’m also the farthest person from Paloma’s end user -- I hate social media, and I do not shop. As someone who lives under a rock, I am not sure that I will get this, but I’d love to understand what I’m missing.”

If you’ve ever had the joy of meeting Kelsey, you can probably guess exactly how this meeting went. After roasting me just the right amount for my luddite ways, Kelsey blew me away with her expertise in the e-commerce messaging experience, her perspective of the market landscape and limitations of existing e-commerce infrastructure platforms and messaging tools, and her insights into the still nascent but burgeoning market of messaging-first -- and in some cases, messaging-only -- commerce

Over the course of our next few meetings, it became abundantly clear that Kelsey, her co-founder/CTO Zach Podbela, and their team are onto something special. With customers like Joybird, ThirdLove and M.Gemi seeing 2-10x increases in conversion rates and a unique product suite, they have set the foundation for a category-defining platform. 

Earlier this week, Paloma presented at Facebook’s F8 conference and launched the first version of IG DMs, with Paloma’s Instagram Sales Inbox. With the tailwinds of social commerce, we are thrilled to partner with Paloma as they empower not just leading brands but also the long-tail of indie merchants selling one-of-a-kind products in one-on-one exchanges.

If you run an e-commerce business searching for tooling to build your messaging storefront, sign up for a demo here. On that note, I’m off to try this online shopping thing ...


Introducing Noteworth's Connect App - a one stop shop that helps #patients take control of their health, and better manage #chronicconditions and medication compliance!

When clinicians "prescribe" Noteworth Connect, patients are empowered and actively involved in their care plan via a single, intuitive app personalized for their unique care journey. From completing pre-visit forms, to tracking medication compliance, to meeting with a provider, patients can see a clear picture of how their health is progressing, all from the comfort of home.

Read full article here

Legacy Portfolio Spotlight: TripleLift

Yesterday, we had the great fortune to announce TripleLift’s $1.4B majority acquisition by Vista Equity Partners. As I read through the excited messages on my subway ride home, I couldn’t help but think about the pride and joy that the TripleLift team must be feeling.

In many ways, TripleLift symbolizes the best of venture capital’s potential. We were blessed to invest in Eric Berry, Ari Lewine,  and Shaun Zacharia as they were coming out of the Entrepreneurs Roundtable Accelerator (ERA). From the very first pitch, their vision was clear: “The web is going visual.” Pinterest was beginning to gain traction, and they could see where the puck was going three moves out. 

Though they encountered some hurdles along the way, they never lost focus on their belief in the visualization of the Web. Laconia’s thesis today grew out of our legacy investment in Triplelift, but more so in Eric, Ari, and Shaun.

With each of our investments, we focus on three key pillars: operational execution, sales acceleration, and capital strategy. TripleLift nailed all three.

When it comes to operational execution, they ensured nothing was overlooked. Each investor update not only included the traditional boxes that needed to be checked, but also emphasized corporate culture and employee wellness, which we found forward-thinking. We were also impressed with how they continued to upgrade their team as the business evolved, balancing loyalty to the person and responsibility to the company. 

On the sales acceleration front, there was a period in the company's lifecycle when they saw the future of ad distribution becoming more programmatic. Those early partnerships accelerated their growth at a time when programmatic ad buying was also in its infancy. 

But what truly separates TripleLift from the rest of the pack is their capital strategy. They checked their ego at the door and based their success on their growth instead of valuation, building a market leader on less than $20 million of total capital raised. On numerous occasions over the past 9 years, I am sure they’ve had numerous options to exit, and the strong foundation of their business enabled them to stay on course toward their long-term vision. 

To our co-investors (True Ventures, Edison Partners, NextView Ventures, Inovia Capital, ERA and all the others): thank you for your partnership over these past nine years. And, most importantly, to Eric, Ari, Shaun, and the other team members we’ve had the pleasure of getting to know: thank you for your trust, and congratulations on your remarkable achievement. 

We are proud to remain investors in TripleLift and look forward to having Vista Equity as part of the team. The journey does not end, and one could say it is only the beginning.


TripleLift Announces Majority Investment Buyout by Vista Equity Partners Value at $1.4B

TripleLift is the latest company in the ad-tech space to announce a liquidity moment with a “majority investment” from Vista Equity Partners understood to be $1.4 billion.  

The two companies announced the agreement earlier today with the deal expected to close in the second quarter of 2021. Eric Berry will remain as CEO and will continue serving on the board of directors.

Read full article here

Two Worlds of Venture

Over the weekend, I tweeted offhand about my frustration with the buzz around early stage venture rounds these days: there’s so much discussion of companies raising lots of money very quickly, when my observed reality from speaking with dozens of seed & pre-seed founders per week is the exact opposite:

This observation struck a nerve, both publicly and privately. Aside from sharing that they felt seen, lots of founders also reached out to me to ask why this is happening, so I thought I’d share some thoughts on the topic.

The notion that some founders raise money more easily than others is not a new phenomenon in and of itself. Fundamentally, if you are not able to close an investor (whether they’re an institutional fund or an individual angel investor) there is only one reason: they don’t trust you yet, and they don’t believe that you will build a venture-scale company. This is the objection that you have to overcome.

So, how do investors build trust & belief? At later stages (e.g. growth equity), investors typically have somewhat objective criteria and some amount of data to leverage such as revenue, growth rates, cohort retention, customer references, etc. They have some evidence that you have, at least in part, achieved what you had set out to achieve earlier in the life cycle of the business (though there’s probably a fair amount of voodoo and vibes at play here, too).

At the early stages (pre-seed, seed, and in some cases, Series A), I’m afraid most people will not like this answer: given the lack of data on the business itself, investors place an extremely heavy emphasis on the founder & the story they’re telling.

*deep breath* 

I know this is frustrating to many people, in part because it is so subjective and unspecific. How do investors determine if they “trust” and “believe” the “founder” and the “story”?

Your mileage may vary depending on the investor, but here are my observations on what venture investors frequently prioritize in making these judgments, in order of importance:

  1. Personal familiarity, or first-degree connections: investing in founders they already personally know through some prior experience. Maybe they backed the founder’s previous company, worked together at a previous job, or went to college together, but through something, they already have a high level of trust. (Unsurprisingly, when companies raise big rounds out of the gate, this is often the case.) 

  2. References/vouching/warm introductions, or second-degree connections: investing in founders whom someone they trust already trusts. Maybe a close co-investor at a different firm backed this founder’s previous company; or maybe the founder was an employee at a company that the investor has already backed, and the co-founder/CEO has provided a glowing recommendation (and possibly has invested in this new company themself!). Absent first-degree connection, trust by association goes a long way.

  3. Signaling, or prestigious heuristics: This is sort of analogous to “Nobody gets fired for choosing IBM”; in venture, as far as I know, no one has gotten fired for choosing a YC, Stanford, or ex-unicorn founder.

  4. Credibility: Failing the above, investors will seek comfort in a convincing narrative and some form of “traction”. VCs seek alignment between the founder’s story and their own upside expectations (could this be a billion dollar business?), as well as a clear articulation of the path to building such a business within existing (and future) industry dynamics (how do you get there?). In conjunction with a clear vision, investors search for early proof points, which could be undeniable user/revenue growth, referenceable customers, formal recognition of the founder as an industry leader, or more. But there’s got to be something that, in the eyes of the investor, makes this founder’s story, vision, and momentum stand out above the rest.

At the risk of beating a dead horse, I can’t help highlighting that the heavy reliance on 1-3 above is a major driving factor for the homogeneity of VC-backed startup founders, given that historically, prominent elite institutions skew demographically toward those who are white, male, and wealthy. If you’ve ever heard the saying that underrepresented founders have to be twice as good to get half as much, this is why: without the advantage of circumstantial privilege & long-standing personal relationships, undeniable performance (#4) is often their only way to get investors over the trust & belief hurdles. 

(Slight aside: You might be thinking, aren’t VCs supposed to be risk-takers? And who’s to say that funding ex-Ivy League, ex-unicorn founders will even result in good returns?!? Not to defend VCs’ reliance on elitism, but this is as good a time as any for a reminder that VCs are fiduciaries managing other people’s money. They have convinced numerous people & institutions to entrust them with a pool of capital to deploy into an undetermined portfolio of high-risk companies. So at minimum, VCs generally need some amount of plausible deniability that they’re not recklessly flinging cash … even though the more we go down this rabbit hole, the less that sounds like a bad idea … )

Alas, back to reality. This is the current state of venture investing. If you are a founder who is not already buddies with tons of GPs or an obvious fit for VCs’ “pattern matching”, what do you do?

  • First, consider whether raising venture capital is even the right move for your business. This is a topic for an entirely separate post, but really think about whether capital is the gating factor to your business’ growth and whether acceleration is critical to the ultimate success of your business. If money is not the bottleneck and time is not of the essence, there are likely better uses of your time than fundraising.

  • If you are convinced that raising venture capital is the right path for your company, you will likely need to rely on self-funding and non-VC funding to get to certain milestones (the credibility piece mentioned above) before you can raise from venture funds. (How do I raise an angel round if I don’t know anyone who can write a $25k check? Great question, and a topic for another blog.)

  • Plan to meet people early, whether they’re angels, advisors, or VC funds, with the intention of building relationships with them over time, so that you can establish mutual trust. Mark Suster wrote about investing in “lines, not dots” a decade ago; this framework remains true today. If you do this well, over time, you end up with the coveted personal familiarity that investors value so strongly, and you will be in a strong position to then run a tight fundraising process. (For reference, at Laconia, I could not tell you offhand where most of our founders went to college, but I can confirm that we got to know most of them over 6+ months prior to writing a check. Sometimes, there are no shortcuts, and thoughtful, long-term relationship-building can be the most powerful lever to bridging network gaps.) 

  • As you meet with investors, be sure to ask what concerns they have or what gives them pause about your company. Take each individual answer with a grain of salt, and try to spot recurring feedback to refine your pitch over time.

  • Fiercely protect your time and trust your instincts. In your research and early conversations, qualify investors and ensure that they are a relevant fit for your business at all based on their investment strategy, fund size, and check size. Separately, some investors, for whatever reason, will be insurmountably biased against you or your business. They may be implicitly or explicitly sexist, racist, xenophobic, otherwise discriminatory, or just flat-out allergic to the sector you’re operating in. The best thing you can do in this situation is trust your gut and waste as little time as possible with them. Your time is better spent finding the people who are real prospects for you than convincing the ones who aren’t.

But Geri, isn’t there so much more capital out there now than there was before? I keep hearing that capital is cheaper than ever, yields are low, funds are huge, and money needs a place to go, so shouldn’t it be easier to raise now? 

This line of logic is conflating multiple things. Yes, there is more venture capital to be deployed, but the distribution of this capital is by no means evenly distributed. All the data I’ve seen shows that at a fund level, this capital is disproportionately concentrated in a relatively small number of very large funds, which does not bode well for founders who are raising their earliest rounds and/or not well connected within the relatively insular ecosystem benefiting most from this boon. The fact that an “in network” founder who could easily raise $1M pre-product ten years ago could probably raise $10M pre-product now thanks to the influx of new capital does not necessarily mean that an “out of network” founder who struggled to raise $500K ten years ago would have any easier of a time now. If anything, the widening of the barbell makes it even harder, as “in network” competitors consolidate war chests faster than ever before. This acceleration does not mean the first-movers will ultimately win, but it can certainly make underdogs’ early fundraising efforts harder in the meantime.

Of course, there is only so much that founders can do to overcome these structural barriers. I recognize that many investors, especially those writing bigger checks, do not necessarily have a goal of identifying opportunities that don’t fit the typical mold at the earlier stages, rather than “chasing hot deals”. But for those who do have this goal, the onus is on us to change our processes: 

  • Prioritize proactively meeting founders outside of our immediate networks. At Laconia, we evaluate all cold inbound pitches and have been doing open office hours every week for 3+ years, through which we’ve met hundreds of founders whom we’d likely never have encountered otherwise; 10/10 recommend this, I hear it’s even trendy now!

  • Push for more objective decision-making/benchmarking. Are you applying your investment criteria uniformly? Are you evaluating founders from different backgrounds in comparable ways, while still being mindful of potential differences in context and culture?

  • The early stage venture industry needs more people, with more diverse backgrounds, to play a role in spotting and supporting true outliers. How can we create more seats at the table beyond the constraints of traditional VC job structures, which are limited in both number and scope?

Ultimately, the data will show if we’re making any meaningful progress. If 2020 was any indication, in times of uncertainty, VCs double down on their existing networks rather than expanding their reach (e.g. here and here). We have 9 months left in 2021 to move forward instead. 

If you’re still with me, thanks for reading! As always, I’m at geri@laconia.vc and geri_kirilova on the dreaded bird site.