Jean Sini invests as General Partner at venture firm Partech.
He's been investing since 2011, and has backed Treasure Data (sold to ARM in 2018 for $650m+), Canva (currently valued at $6b), People.ai (backed by Lightspeed Ventures, a16z, and Iconiq), Antheia, ProdPerfect, Clubhouse, Datakin, Firefly and Medigate amongst others. A repeat founder with 20+ years of software engineering experience, Jean's held CTO roles at Activeweave (sold in 2007), Mint.com (acquired by Intuit for $175m in 2010), One Kings Lane, Fountain (acquired by Porch in 2015) and Cadre.
How it all started? How did you decide to enter the venture investment business?
A very gradual process. I started investing in startups, as an individual, close to 10 years ago, long before joining Partech.
At the time, I had been living in San Francisco for 15 years, and was busy building startups, typically as VP of Engineering or Chief Technology Officer. For better or worse, many of us in the Bay Area spend pretty much all their waking hours working, talking about work, or hanging out with others working on their own startups.
The whole ecosystem is tight-knit, there are so many people with great ideas: it’s only a matter of time before friends start pitching each other. That’s what happened to me. I jokingly refer to that first phase of my investing career as a crime of opportunity: I started backing companies founded by people in my immediate network whose ideas struck me as compelling, by writing very small checks into their very early stage rounds, causing me very real anxiety! It took me a while to stop freaking out about it.
I didn’t think then it’d become my full-time job.
Initially, I found it a great way to actively engage with founders around me, and it also contributed to cross-pollinating engineering and product practices. Investing in, together with advising, early stage companies from a technical standpoint meant we all got better at our jobs, prioritizing and validating roadmaps, leading teams, building sales playbooks, etc. by comparing notes. I was constantly in contact with other founders, other ideas, other teams, other approaches: that’s what I found most rewarding.
I kept ramping up that work and at some point, a few years back, realized that’s what I wanted to spend all my time on. So I left my last CTO job to do just that .
About 2 years ago I caught up with a close friend of mine, a partner at Partech, who introduced me to the rest of the team. After getting to know everyone, I joined the firm about 18 months ago, as the thesis for the fund lined up strongly to what I feel I can contribute.
What was the most memorable startup you ever supported?
One of the earliest investments I made, in 2012, was in Melanie and Cliff, the two co-founders of Canva, currently valued at $6b. It’s one of the most amazing companies out there, period. But the way we got to know each other is pretty funny.
We first met through my friend Bill Tai, an astounding investor in the Valley. He had met Melanie in Australia, and convinced her the best way to jumpstart fundraising for Canva was to attend a kiteboarding event he was organizing on Maui!
Melanie and Cliff did just that: I met them on the beach on Maui, on their way from Sydney to San Francisco. It turns out I had just moved into a new place, with a guest bedroom, so I offered them to crash for a few days while they got their bearings and kicked off their raise.
We ended up spending 2 months together: they’re incredible. I watched them leave every morning for Sand Hill Road, to pitch several investors, and upon returning home every evening, get to work refining their pitch based on the day’s feedback. Then at night they hopped on a call with Australia to run the company, many time zones away! It felt as though they never slept, yet never tired.
I was so impressed by those two, by their work ethic, energy, grit and sheer determination, that I asked them to let me invest. I also became an advisor to the company. They’re doing tremendously well, and have long outgrown any advice I could give them, but this remains my most memorable initial interaction with a founding team.
How many startup projects do you review per year?
We were initially anticipating our activity would go down, 6 months ago, with all the disruption caused by COVID-19. Instead, we got busier. Candidly, we became more productive, because we’re not traveling to or between meetings. I meet 25 to 35 startups a week, and about two-thirds of those are initial meetings.
How startup teams usually find you? Do you wait for inflow or scout for interesting ideas and perspective teams?
We are both scouting actively, and handling inbound deal flow. Through our network, we get a lot of introductions. We aren’t difficult to find, and receive cold intros like everyone else. Still, an introduction made through someone we worked with lends a degree of initial trust .
Personally, I enjoy the outbound, proactive process: I invest significant cycles researching specific industries and getting to know those ecosystems.
I research companies well established in the space, their challengers, the needs and pain points they address, their archetypal customers, etc. That initial effort yields initial conversations with founders that prove much more valuable for all: instead of discovering the most basic facts, we can focus on ways to be helpful to each other and the ecosystem. This is my favorite way to engage.
How you select startups to support? What are your criteria?
The process varies based on the stage of the company. These days I’m predominantly focused on Series A and Series B rounds.That’s different from pre-seed or seed, with very little data to go on and as such almost entirely a team bet.
At the Series A stage, we expect to see traction.
By definition, the business of venture is about embracing calculated risk. Among other things, I’d say the quality and robustness of product-market fit matters tremendously.
To experience any traction at all, some initial form of product-market fit is required, but to grow and meet the needs of more customers, with strong unit economics, particularly in the face of competition, Series A companies need to keep perfecting that value proposition.
So, my basic criteria are around product-market fit: how engaged are current customers, how deep is the addressable market as it stands. And because we’re early in the lifespan of the company, how biased is the team toward a combination of action and learning? How quickly and continuously can they evolve to better meet the needs of a broadening customer base?
What kind of pitching do you prefer: boring numbers or a show?
I’m human, I want to get behind a great vision. But I then look quickly for tangible facts.
Founders invest a lot of time in perfecting their pitch. Together with their deck, it best expresses their vision via a compelling, succinct narrative. As such, I very much enjoy experiencing the result of that work: by all means, walk me through the deck!
Occasionally, I meet founders who master the arc of their pitch to the point they communicate it flawlessly without a deck. But often the deck is a great mental tool, frankly for us both, to ensure we hit every key fact in a crisp, crystalized fashion: from vision, to traction, to market, to competitive landscape.
And the faster we go through the basics, the sooner we get to the more tangible elements of what makes you unique.
At some point in that initial conversation, I’m looking for the more concrete elements, too – in terms of the underlying technology, the reality of the problem being addressed, the way the product looks and feels. I’m also looking for details on current status, projections, and go-to-market approaches to reach specific milestones.
When do you typically invest in a company?
We manage about $1.5b across 3 funds, each stage-specific (seed, venture, and growth). I’m a part of the venture team, focused on Series A and B rounds.
What industries you’re interested in?
I’m obviously opportunistic: if I meet with a great team that seems to be addressing a problem causing significant pain in a large market, I’m paying attention.
That said, I proactively spend time researching a couple of verticals, that I’ve grown affinity toward based on past experience.
Since I’ve spent many years as CTO and VP of engineering for several companies, I’ve used a lot of developer tools, data and machine learning platforms, and other similar productivity services benefiting product and engineering teams.
Similarly, I work on a lot of Fintech opportunities, an area of particular interest given I spent years building Fintech companies.
Last, Healthtech. I think we’re at a unique juncture where healthcare and software are combining to enable great outcomes for patients, and we want to be an agent for good on that front.
Geography of your interests?
The firm invests globally: we’ve made investments in the US, Europe, Israel and Asia. One of the very strong elements of our identity is how we help founders from Europe bring their business to the US market, and vice versa.
We have nurtured a strong network of corporate partners, LPs, and portfolio companies to help with that transition.
Individually – because I’ve spent my entire professional life in San Francisco and New York – I invest predominantly in these two ecosystems and in transatlantic companies because that’s where most of my network is.
You have an office in Dakar, Senegal, why?
To be valuable partners to entrepreneurs there, we established a separate fund run by two partners and a full team, operating out of Dakar. Because the ecosystem is younger in that region, the fund is continent-wide and stage agnostic.
What is your due diligence procedure and how long does it take you to cover the whole way from the first meeting with founders to contract and check signing?
The answer, as always, is “it depends”, but we usually go from first meeting to close in under a month. The process is fundamentally about building, together with the founders, conviction that we’re a strong mutual match.
It’s a cliché in venture: the relationship between founders and investors can outlast a marriage. So it’s critical for both parties to feel the partnership is right.
Our role in the process, as investors, is both to do our homework swiftly, and to establish that we have something to contribute beyond just funds.
That said, velocity in running the process to completion is crucial: we’re all aligned on the fact that founders should be spending their time building, not raising. And the most uncontroversially high quality teams get funded extremely quickly, receiving multiple term sheets, so from a competitive standpoint moving rapidly matters too.
What that means is I invest in a lot of time and energy in pre-work.
Both to gain a strong understanding of the ecosystem, before we even have our first conversation, and in order to be a valuable partner to founders, regardless of whether or not we end up investing, through introductions or by comparing notes on the industry at large.
This yields much more specific conversations, where we focus on what’s unique about a team and a company, rather than on attempting to grok an entire industry from the ground up during that first meeting.
Target multiple on exit?
We aim to be performing as a fund overall, in the top quartile of the industry and aren’t merely looking at each individual investment. That said, there’s a long, risky, bumpy way to go between the Series A round and an exit, so we invest when we have a high degree of conviction we can 5x or 6x our stake.
What is your ownership target in the investment?
While that’s in part affected by market conditions, we model our venture fund around a 15% to 20% ownership target at Series A. As mentioned earlier, a healthy relationship with the founders and team is key, and we always aim for a valuation that benefits the business, thus all parties, long term.
While a Series A round is not as early as a seed or pre-seed round, it’s still the beginning of the journey, and as such, we think about the long path ahead more than the few steps behind us, and I want to make sure that the founders and later investors feel they have sufficient upside in the long term success of the company.
My advice to founders is to always think one round ahead. In other words, balance raising enough to meet your business milestones (so you raise the next round from a place of strength), with targeting a valuation that doesn’t put you in a bind in terms of revenue expectations when you raise next.
Lastly, it doesn’t seem valuations have dropped, the way people had initially feared, due to the COVID-19 crisis. This leaves our ownership targets and investment amounts unchanged.
What qualities you are looking for in startup teams?
Some of the best teams I know are obsessed with their customers. What do they need, and how does that shape the product?
A great example is Oleg Rogynskyy, founder & CEO at People.ai, a company I invested in very early. Before making the investment, I kept meeting with Oleg every couple of weeks, for a few months, to catch up on his vision for the company as it was forming.
What was amazing was his combination of a very clear vision for the company, with an endless appetite for meeting future customers. He had no product yet, but instead of building a prototype in isolation, he kept meeting with the people in his sweet spot and came back each time with a refined version of what the initial product would need to accomplish.
That willingness to confront reality, validate and refine assumptions constantly, is essential to survival.
You also need to assess the relative strengths and weaknesses on your team, and know how to attract complementary talent.
Last, it’s key to invest early in great communication, and effective processes within the team, to ensure effective collaboration and to prevent the team from collapsing under its own weight when it no longer fits in a room, virtual or not.
Investors prefer to work with teams. But have you ever supported a one-person startup?
I have. The key for a solo founder is to quickly recruit their minimum viable team, so they can execute.
Who you would prefer to work with, Steve Jobs or Steve Wozniak?
They are both amazing individuals. And while both technical abilities and a great vision are required to get the company off the ground and keep it growing, a knack for constant evolution, the ability to reinvent, is just as critical, along with the humility to keep learning.
What are your red flags?
One of the major red flags is discovering some inaccuracy in the narrative, like exaggerating numbers, or misrepresenting the nature of various partnerships. Being honest and transparent about what’s going on in a company is essential.
Thankfully, that’s rarely an issue. More frequently, we’re concerned when a company is struggling to launch, to go from an idea to a product in the market. We aim to gauge an entrepreneur’s start learning from feedback, and iterate.
Have you ever rejected a startup and then regret it?
It’s still too early to tell, I’ve only been at the firm two years. I keep track of every company I’ve seen. By the way, when I’m not investing, I still hope I’m wrong, because I want every founder I meet to succeed: as a long time entrepreneur myself, I know how much of their lives founders pour into their companies.
Can you name the three most breakthrough startups in history?
The world would be a very different place without Google. The world might turn out much better off thanks to Tesla, accelerating a transition away from combustion engines. In more recent history I’m blown away by what Zoom was able to accomplish. And Canva, in my portfolio, has done an incredible job changing the way people design. So that’s four.
Can you name industries you really like, yet will never invest into?
I don’t know enough about the space to invest in hardware, so while I see amazing changes introduced into everyday life through hardware, I’m very unlikely to invest there.
Has your VC approach changed after the COVID-19 started?
We’re certainly cautious about industries that are suffering, either due to direct or indirect effects from the pandemic. Travel is an example of obvious, short term concern.
But there is also a lot of opportunity for positive change, emerging from the crisis: what is the metaphorical office going to look like in a few years? What about life in cities? So, while we haven’t altered our overall approach, we added an extra lens to assess industries in terms of COVID fragility or anti-fragility.
So, is COVID a threat or opportunity?
Squarely an opportunity. As I mentioned, I’ve been able to meet with more founders, have been able to be a little less concerned about their physical location. This opens up the ecosystem to more teams.
Are you satisfied with what you do, or do you think to apply your knowledge and skills to something else in the future?
I’m very happy with how I spend my time. I’ve been on the other side of the table, building, and for me being an investor feels like a logical next step where I get to back the same type of people I have worked with for so long.
What qualities, you think, are important for a good VC?
Ask me in 10 years, if my investments are any good. The ability to reach a decision quickly is essential. It’s no secret that the best companies raise money very quickly. You may have the best framework and criteria for picking, but if you’re not aware that an incredible company is raising, you’ll never be able to run your process.
And if you’re too slow, it won’t matter either, because teams will close with someone else. A certain degree of willingness to take on risk is key.
Finally, you need insatiable curiosity toward the industries and trends you invest in: always be learning.
Is venture business chess, checkers, backgammon, go, card games?
Poker. It is definitely a world where you’re making decisions with incomplete information. Even the best investors out there don’t win every hand. I’m not sure it’s a perfect match, but it’s certainly not chess.
