Judges on Fire: Jessica Li, Head of Content, Elpha

In our Judges on Fire series of podcasts, we aim to let you get to know our judges a little better. They also get the chance to share their wisdom and tips about entering the Tech Trailblazers Awards. For our eighth outing we are catching up with Jessica Li, Head of Content at Elpha. Jessica is one of our newest judges, having joined during the 2020 Awards.

In a fascinating conversation, Jessica describes her past experience and what she looks for in an entry to the Tech Trailblazers Awards. Having been on both sides of the startup process, both involved with startups and also being part of deciding Angel investments, Jessica shares what she’s learnt, including the importance of founders and that you can’t get everything you need to judge a potentially worthy investment with a quick internet search.

Listen to discover what key piece of advice that can set you free which Jessica would give to her younger self. So, over to Rose Ross, Founder of the Tech Trailblazers Awards, as she interviews Jessica Li in our eighth Judges on Fire podcast.

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Interview transcript

RR: Well, I’m delighted to welcome to the first Tech Trailblazers Judges on Fire podcast of 2021, Jessica Li. Jessica has a number of roles and we came across one another when you were with Soma Capital, but you’ve also been very heavily involved as Head of Content for Elpha as well. So, welcome Jessica, great to see you.

JL: Yes, thank you so much for having me, I really appreciate it.

RR: No problem. So perhaps you’d like to give us initially… not everybody who is listening will have had the opportunity to meet you, or know you, so perhaps you could give a little bit of an overview of your startup journey, and your involvement in the startup community, in the tech community.

JL: Yes of course, so a little bit more on myself. I’m currently full-time with a company called ZAGENO which is basically a B2B procurement marketplace in the life sciences, sort of like an Amazon for the life sciences, for biotech startups, pharma companies, labs, researchers etc. I can go to more easily and more seemlessly procure other lab equipment, materials, and supplies, all in one place. And so, doing growth marketing here, our growth marketing team is just three people, two including myself when I joined. The company is a little bit larger, a growth-stage startup based in Boston and Berlin, so our growth team is relatively small.

That’s what I do full time and then part-time, as you alluded to, I head content for Elpha which a community of women in tech. We now have a little over 40,000 members worldwide which is super-exciting, so I manage all of our featured posts, published twice a week, and then also our asynchronous twice a week office hours, “Ask me Anything”, as we call them with really incredible women on or off the platform. So those are my two main roles, but then I also do some other content things including heading content with Harvard in Tech and Techstars Boston, and also writing for Pinduoduo which is an ecommerce company in China, and then previously was in the investing world, as you alluded to, as working at Soma Capital prior to ZAGENO which is a sector agnostics fund focused on enterprise. So, I’m known as their first full-time which was super-exciting, so did everything from sourcing to diligence, to content, to community and portfolio operations, and some industrial relations as well, and they’re based in San Francisco, and Head of Content with Elpha there as well part-time still.

And then these days to stay connected to the startup world, I also mentor with several different accelerators, including Techstars, and Alchemist, and Acceleprise, and Plug and Play, so pretty much pre-seed accelerators across all kinds of spaces and sectors, and more recently IndieBio as well which is a biotech specific accelerator given my new role at ZAGENO. And then doing some Angel investing on the side with different groups including Grishin Robotics and the Predictive VC.

Prior to all of that, and prior to Soma, I spent some time in the startup world working with Morning Brew and Luxe, also some time in public markets investing with an endowment, a family office in Northwestern Mutual, and then also some time in investment banking at Morgan Stanley, and then finally some time at other early-stage venture funds including General Catalyst which is how full-circle I came back to be connected with ZAGENO when General Catalyst led our Series B back in 2019. And so yeah, that’s a little bit about me.

RR: Wow, busy lady! So, thank you very much for making the time to chat, that’s brilliant. Well, you joined us as a judge quite late in the day unfortunately in 2020, so you’ve not perhaps had the exposure to the startups that we’d like you to have, and unfortunately due to a prior commitment you’re not able to join us for the showcase that we’ve got with some of our winners, that’s happening on the 25th. But aside from that, obviously you have a vast amount of experience on both sides of the fence in the startup world, both from an investment perspective, of which you’re obviously still involved, and within the startup side of things. So, when you’re judging what kind of startups are going to attract your attention? What’s going to light your fire around the kind of people who participate in awards?

JL: That’s a great question, I think for me especially in the early stage which I imagine is most relevant for most listeners, and that precedes sometimes even Series A stage, I think what is really important to me is first and foremost the team, because the product and subsequently the market and everything around the more fact-based aspects of the company can change and shift, as the company goes through the process of finding product market. A product-type company is pivot to FinTech which seems totally different, I see it as a more famous example Embark Trucks which is one of our former portfolio companies at Soma Capital that’s now a very big company, they had a massive growth round I think in late 2018, if not, late 2019, bought by Tiger Global which is obviously a very well-known, very big, and very global growth fund.

When they first started back in the seed stage when they were in Y Combinator they started off as an autonomous golf cart company which if you over analyse that market it sounds silly, or small, or just not a big pain-point, and if you had been stuck on that you would have missed out on a really great investment opportunity as an investor, as a judge, or supporter of the startup community. And now obviously they haven’t yet gone public, they’re still a private company but doing super well by all metrics, and they’re doing autonomous trucking which is of course something of a more reasonable market and big market – big growing market that they’re really dominating.

And so, I think in this case really focusing on the founder and really understanding him or her and understanding how they think and how they see the world, obviously pedigree and prior experience is a factor, but I don’t think it should be an overwhelming factor. I think it’s much more about there’s more quality there and harder to judge, or less black and white aspects of a founder, their perseverance, their resilience, if they’ve had experiences in the past prior to founding this company or whether they’ve had to build and rebuild over and over again. One of my favourite founders that I met through my work at General Catalyst, it’s really interesting because he was actually a researcher in his past life prior to founding this FinTech company, and one thing that had happened to him is that he was doing this multi-year-long bio project and he was working with petri dishes – I’m not too sure of the details, but one of his eyelashes dropped into the petri dish in the last minute or final mile, final stretch of his project, and I don’t think it ruined his whole project – that would have been a little bit drastic, and hopefully he had some backups, but it did throw him through a loop and threw his project out of sync.

Just small things like that where you have to re-do, a two, three, one-year long experiment that you’ve poured a ton of time and a ton of heart and energy into, but you’re not giving up and just sucking it up and persevering, and being resilient, it doesn’t have to be anything super-drastic, obviously it could be, but it could be something more professional, more academic like that, just proving your resilience.

So, looking for attributes like that in founders, and also looking for a well-rounded team especially of founders who have worked together before, because they think a lot of times there is this big difference between people who met each other and can get along over drinks, or over dinner once a week, or once a month or whatever, like all of our typical general friends, but it’s a very different experience to actually work together and be collectively accountable for a deliverable together. I think that’s obviously something founders do literally 24/7, or co-founders do 24/7 together, and I think a lot of times people have this misconception where they get along well with someone over, again, drinks, coffee, dinner etc, but it’s a whole different experience to work with them. So, I like to see when founders obviously not always or not mandatory but it’s always really helpful to see that they have worked together on something in the past.

Finally, it’s also really helpful to see founders who are very process-oriented and not outcome-oriented. Obviously the company will have an amazing outcome at the end and that’s really great, but it probably won’t come if at all for 7 to 10 years in those earlier stages. So, founders need to be very process oriented and love the ride and do ridiculously challenging things just for fun.

I met another founder back when I was at Harvard. He’s building a 3D printing farm which is super-cool, and they’re still at an early stage, so it’s hard to say what will happen, but one thing he said that prepared him really well for his founder journey, beyond classes, jobs, experiences, is just his process of tinkering and working on different projects because that was this experience of doing something, insanely difficult not for a grade, not for an outcome, not for a pat on the back even, not for money but really just to enjoy the process, and enjoy the process of actually creating something from nothing. That’s obviously what founders do for limited short-term or medium-term rewards. So it’s really important to look for people who have that quality and characteristic.

RR: Indeed, and certainly from what you say I think is true, about the team and multiple co-founders; I’ve certainly found that a lot of our winners have people who’ve worked together in the past, who set-up companies together, and I think that’s one of the very exciting things about enterprise tech is that it’s much-much easier, because you tend to see with enterprise tech that you are repeat offenders, if that’s the right word. That people can replicate it because they understand it, they’ve got the access to the contacts from a financial perspective and from a commercial perspective, and they kind of have the blueprint for success of what they need to put in place and the processes, as well as the people.

So, obviously you’ve talked a little bit about Elpha as a female focus, and obviously that’s one of the things that particularly drew us together. Obviously Tech Trailblazers is founded by a female, we have our Female Tech Trailblazers Award which focusses on ladies as well as the male; what are you seeing with the feedback within Elpha around what’s happening? It’s been a very challenging time, as everybody likes to point out, and how are female founders and female senior execs in startups? What’s the mood, the feeling out there at the moment?

JL: Yes, that’s a great question. I think as you’ve alluded to it’s been a very challenging time, obviously for everyone with COVID and all that’s going on in the world right now, in the US, abroad as well, and obviously a lot of the data has recently shown. There was a report from Q4 2020, and then obviously earlier this year in the US, at least with their job support in the report in Q4 which is more on funding, and showed that there was a significant decrease in funding to female founders, or female-led companies, even relative to investment in male firms. Then earlier this year, earlier this month with the latest job support in the US it showed that women lost many more jobs in the prior quarter than men, many, many more which is obviously very disappointing. There’s all this research and hypothecating that’s showing that a lot of times women leave the workforce, not because they can’t find a job perhaps, I mean some of it is due to that, but also they voluntarily leave the workforce and they’re not even counted in that unemployment rate or job-loss rate because they are voluntarily withdrawing, but because they need to take care of housework and children, and education as schools remain closed, or parents just don’t feel comfortable, understandably, putting their children back into schools given the COVID situation is still not great, to say the least in the US, or other countries as well. So, lots of concerning data on that front in addition to all the knock-on events that are affecting everybody.

So in terms of Elpha and just a bit more anecdotally of what I’ve seen elsewhere, I think there’s definitely been a lot more vulnerability which I think is great, because I think the worse thing, or one of the worst things you can do, is keep it all inside of you and feel like you’re the only one feeling this way, or that you’re unusual, or something is wrong with you or just bottling it all up, especially when it comes to something that is more emotional and less black and white, or less fact-based, and it’s very understandable and very normal to feel negative emotions with all this going on, especially in the women’s community more broadly. And so, it’s been really great to see more people in Elpha.

We have this feature where once you’re logged-in you can post anonymously. So it’s a cool blend where you have to be logged in, so not just any random trawl robot, whatever, on the internet can post, as you sometimes see on Reddit or other not-great anonymous forums. So, it’s nice that you do have to log in and be an actual member of the community and we let people in, not on a titles or seniority basis but more on an intelligence base and making sure that regardless of your age or background that you’re really positively intentioned. So, I think that’s really nice to have a diversity of people in every sense of the word, who all have really positive, really good, very collaborative and supportive intentions.

So, once you’re logged-in you can post anonymously, and so it’s nice because people feel like they can be more vulnerable and be more open, especially when it is a more sensitive topic. I recently saw a post where someone said that they’d been crying a lot all the time, and it was posted anonymously understandably, but that’s something that you don’t always talk about in the typical work meeting, or on the typical LinkedIn or Twitter posts, but I imagine it’s something that a lot of us are going through with similar emotions even if not literally crying. Similarly, somebody had posted about this long-term relationship that they were rethinking due to some event that happened during COVID between this person and her partner. And so different things like that, where people are being more vulnerable and being more open in setting an example for others that this is okay and normalising this behaviour and this sense of feeling sad, or lonely, or other negative emotions.

But then also having different community members, many of them not anonymous and you can message them directly if you want to have further conversations, and many of them anonymous as well if they want to just share their own experiences that have been similar. But basically regardless, different community members responding with their advice, and their empathy, and just have a very supportive community. There’s never been a negative comment where someone’s calling somebody out for feeling vulnerable or other understandable behaviours, everybody’s just super-understanding and super-supportive.

So, I think the down side obviously is everything awful that’s going both for everybody, and also for women in particular when they think the silver lining if you will, is that people are more open to being vulnerable, and then in turn people are more open to feeling what they’re feeling, as well as supporting others, and being able to support others. I think a lot of time if people don’t share how they’re feeling and it’s harder for others to obviously know, and to be able to provide that support. So, I think the positive feedback cycle is really good to have gotten started in a more meaningful way during these challenging times.

RR: Yes, it sounds like that type of anonymous being open, and how did you know that was my post?! (laughing) No, I wouldn’t say I’ve been crying any more than usual, but yeah, I think we’ve all had our moments. COVID has certainly tested us all, we’re spending a lot more time on our own, or on virtual conferences. We’re not getting a lot of the support and I think that’s particularly true for everybody. I think it’s great that there is a forum for women to have that, but it does sound like there should, if there isn’t already, be something for everybody really, to have tat ability to be able to say, “Hey, this is not okay for me at the moment, and would like some support.” So, that’s great and I’m glad that people are finding that there, in a huge community of 40,000 ladies, so that’s brilliant.

From your perspective of your experience, two elements really; one is, what would you say is the biggest lesson that you’ve learnt as someone involved in a startup? And then perhaps the biggest lesson that you’ve learnt or seen when you’ve looked at it from an investment perspective. So, to kick off with, what would you say is your biggest lesson that perhaps you’d like to share? Apart from obviously make sure you’ve got some tissues handy.

JL: Exactly! So, to the first part of your question of being part of a startup. I think so many things and obviously my own learnings and own perspective is from somebody who came from the venture world, so I imagine the learnings may be a little bit different, or a lot different for somebody who’s been involved in Big Tech or startup land, or maybe some different type of invest in public markets private equity, but for me from that perspective with that context given, a couple of different things actually. So, one thing is that when I was in VC all of my KPIs that I was being judged on and being tracked on were very output oriented, they obviously involved a lot of hard work, they were very important work, I loved doing it but it was very much things that were almost 100 percent in my control. It was things like how many founders am I reaching out to, how many founders am I talking to, which again is important hard work, but I just email, I just show up to those calls, it’s not inconceivable of how I go about to do that.

It is very much this linear relationship between time and output. You send one email every five minutes, or ten minutes, and that’s how much time you have to put in to send ‘n’ number of emails. But I think in the operator world what’s interesting is that obviously it’s so important to be responsive, just Slack messages and emails, but what really matters is the outcomes and not so much the output. I could send a million emails and if none of them convert to leads nobody really cares! But if I sent four emails and not literally emails, but just for the sake of analogy, and two of them respond positively and speak on marketing qualified leads, or just otherwise are able to move down our sales bundle, that’s much more valuable, and so the decoupling between time and output, and this aspect of working not just hard, but also working smart and also being creative and being to convert challenges, or pushback, or other obstacles. So, basically this kind of 80/20 role in some ways where you spend a lot of time sharpening the knife to be able to have these compounding effects that you can reap later-on and not thinking, ‘Oh, this didn’t immediately produce output so it’s no good’, but being more quality over quantity in different approaches and being more strategic and more thoughtful. So that’s one thing.

The second thing is that I think with venture, my relationship building style was very much long-term and broad, obviously because investors, as many listeners may know, spend most of their day taking external calls with founders, new ones, or ones in the portfolio, other investors, partners, etc. which is great, and it’s great to meet so many people in the eco-system and built so many long-term relationships but you’re not talking to the same people every single day, and when you are talking to them once every few months, if not once total, or once a year, you’re very much in this position of sharing information; what deal flow are you seeing, what macro trends are you excited about, which is a super cool conversation of course, but it’s very different from talking to the same three to five people every single day and being collectively accountable for a deliverable together. So, that’s been very much obviously my work day in the operator world, very few if any external calls day-to-day, and very much catch-up calls, touch bases, meetings with the same three to five people I work most closely with.

So, very interpersonal but in a very different way has been really interesting, it involves a lot more empathy as well, because I think when you’re just talking to someone and sharing information that still requires some empathy, you need to know what they’re curious about, but it’s a little bit more direct. Whereas when you’re working cross-functionally you need to more implicitly and look at the non-verbal cues of what people care about, what their instincts are, what their work styles are, what their priorities are, what their OKRs or KPIs are for their department or for themselves individually, and so that kind of process of building deeper empathy and working with people more closely over time has been really interesting to learn too, and certainly skills that are really invaluable. So, I’m really glad I’ve been able to build upon it in the operator world, and so that’s on being part of a startup situation.

On the other side of your question, other parts in terms of having invested in previously and a little bit, so now as a Scout and Angel, as an investor, what I’ve learned about startups or just learned in general in that world. I think a couple of different things as well, so one I think which has been interesting is going to that point of that long-term relationship building, obviously it’s a little bit less relevant if these are folks, you’re seeing every single day and working cross-functionally with, but more those people who are important nodes of your network and meaningful relationships, so people you don’t need to or get to interact with on a daily basis or even weekly or monthly basis. I think what’s really helpful is basically having a ‘give first’ attitude there. I think a lot of times young people, early career people, even founders in many cases they might feel like they’re not in a position to give, because for the young people because they’re young they don’t have as much experience, or if you’re a student even, you feel like you are obviously super young so you really don’t have any experience, and that’s sort of how I felt really early on in my career when I was a student as well, and it was always very much like reaching out to people to ask them for a favour in the form of their time, or their advice, or their introductions. Obviously, it’s great to be able to receive that from people, and of course some people are able to give more than others, and that is somewhat tied to your age or your career status. But I think always having a ‘give first’ mentality is something I’ve learnt a lot through the investing world, because relationship building is just so core to the deal flow you get, to the way in which you’re able to win allocation and to deals, to the way in which you’re able to support founders after you invest as well.

And so, I think basically even when you’re cold outreaching to people, not just saying, ‘Could I please have 30 minutes, 20 minutes of your time, I have these questions’, but talking about ways in which you can help them as well. Even if you’re a university student for example and you can’t think of major-major ways to help, let’s say you’re reaching out to the CEO of a company, or an investor, you actually can, you can offer access to the university networks. I know many startups are dying to hire seniors at university, there’s actually engineers in the early stages, or maybe there’s different startups on campus that you’re able to refer to investors for example, what you’re reaching out to, who you’re reaching out to as an investor, and you’re able to offer access to that university startup.

So, different things like that, or even if none of the above, but you can offer product feedback or organise a focus group if their product is something that you use, or you know a lot of people who use, or what the user would benefit from. So basically, being creative around your ways in which to give. So, I think that’s the first thing that I learnt. The second thing is a lot of times in the venture world, or people early on in the venture world, they have this misconception that you need to focus a ton on tangible things like revenue, or pedigree, or prior experience, and these sort of things that you can ‘touch and feel’ and it’s a sort of concrete fact if you will, they went to X-school, they worked at X-company, and obviously those things are not to be dismissed, and they are datapoints that you should incorporate and be aware of, but I think what’s actually much more important is going back to what I said earlier, is very much there’s more intangible or harder to figure out, it’s not something you can just look up on LinkedIn and know, yes or no, do they go to this school, right away but it’s something that you have to work for if you’re getting to know these founders as people, and how they see the world, and how they problem solve.

A lot of it comes with observation over time, so I think that aspect of the most important factor for a founder is perseverance which is something you can’t always quickly fact check on the internet in a moment’s time, but something that you have to work hard to understand is really interesting. But I think it also makes for much more interesting investment discussions, and much more informed investment decision making, and also stronger relationships that you get to build the founders, regardless of if you invest in them or not.

RR: Wonderful. Well, there’s a lot of advice there. Obviously 2021 we’ll be kicking-off with entries on June 25^th, so that’s one for the diaries, and then obviously putting out to yourselves. As I said, it is a shame you can’t join us for the meetup next week on the 25th, because we actually have our Tech Trailblazers Female winner, Stephanie Fohn from NeuVector joining us for that (update: sadly Stephanie has had to pull out of the meetup but will be appearing in a #FoundersonFire podcast very soon), and a couple of the other judges as well as some of the other winners. But it’s certainly something we’d like to do in the future.

Is there anything else you’d like to share with the listeners, any other pointers or insights that you feel this would be a good vehicle to share on?

JL: Yes, I think one final thing I’ll add that I think I’ve learned throughout the years, sometimes perhaps the hard way, but one thing that’s really stuck with me is, I think a lot of times people have a misconception around what they should or what they need to do. I went to Harvard and obviously I’m really glad and super-grateful for that opportunity but looking back I think I was overly focussed on my career in the first I’d say half of the three years of my experience there, and I think part of it obviously was just something intrinsic in my own instincts or my own motivation. But maybe there’s also inevitably anywhere, not just Harvard, a lot of herd mentality on campus, and I think I kept thinking that I needed to go into these very traditional career paths. I saw many of my classmates a year or a couple of years ahead of me, or my parents talking about it a lot, or people talking about different grapevine investment banking, consulting, and obviously there’s certainly merits and benefits of going into those industries, that can’t be discounted or discredited, but I think a lot of times you need to think less about what society or what your parents, or what your peers, what your professors or mentors expect you to do, and listen more to what you personally want to do.

So, I think that’s something that I would tell my younger self as a piece of advice, and my younger brother is actually starting at Harvard later this year, and so that’s something that I’ll be telling him a bunch as well. I think sometimes you do have to make those mistakes or go down the wrong paths to be able to learn it yourself, and that’s probably the best way to internalise the lessons, but of course internalising it sooner rather than later is always helpful to be able to end up going into the industries, and the domains in which you can feel like you can have the biggest impact and the biggest fulfilment. I think people will ultimately do their best work and are their best selves when they are happy. So I think it’s really important to think about your own optimisation function, and not a job that one from the market if you will, to draw upon, and I’ll make an analogy; but instead of looking at what your peers have, or what they’re optimising for, or what everybody else in the world in your age group is optimising for, obviously that could be a small input if you’re really lost, but I think it’s really important to take the time to know yourself and how you work best and where you work best, what you’re curious about, and be really curiosity driven.

RR: Interesting, great advice particularly for those who are taking the first steps perhaps in that particular journey. Well, thank you so much for joining us Jessica.

JL: Thank you for having me.

RR: So, here’s one of our judges, it has been great to have you on the Judges on Fire podcast, and hopefully we’ll be bumping into one another again very soon. I look forward to it, thank you.

JL: Thank you.