The Diligent Observer Podcast

Episode 38: "Practice Your Thesis Until It’s Muscle Memory" | Stella Foundation Chairwoman Dr. Silvia Mah on Activating University Ecosystems, The Three C's of Capital, and Creating Proud Investment Portfolios

Season 1 Episode 38

Insights from the Chairwoman of Stella Foundation and founding member of Stella Angels who has invested in 160+ women-led startups and co-managed six consecutive San Diego Angel Conference funds totaling millions in early-stage capital

Today's episode explores three ideas that caught my attention:   

  1. Creativity is the gateway to better investing - Silvia's classroom exercises aren't just for students. Her approach to opening minds through creative prompts parallels exactly how angels need to spot outliers that don't fit conventional patterns.
  2. Relationships endure beyond failure - Her experience supporting founders through bankruptcy reminded me how the most valuable connections aren't defined by financial returns but by integrity during difficult moments. 
  3. Muscle memory in pitching your thesis - Just as Silvia has her students pitch daily to build confidence, angels need the same repetitive practice to clarify and refine what truly matters in their investment approach.

I explore these ideas and more with Dr. Silvia Mah, Director of Innovation at Biola University and Chairwoman of Stella Foundation. She brings a rare combination of scientific rigor and investment acumen as both a biochemistry PhD and seasoned angel investor who's backed over 160 startups with diverse founding teams. She bridges academic entrepreneurship with practical investment strategies while pioneering gender lens investing through multiple funds and angel groups. Her perspective is particularly valuable for understanding how university ecosystems can better connect with angel investors to create sustainable startup growth channels. 

During our conversation, Silvia shares: 

  • A "Three Cs of Capital" framework that helps angels understand their full value beyond just writing checks: financial capital, experiential capital, and network capital. 
  • A practical AI implementation technique for angel groups that transforms entrepreneur information into streamlined due diligence memos and project plans for volunteer teams. 
  • The "Angel Conference" model that universities are adopting nationwide to activate alumni networks, educate new angels, and fund campus-connected startups through mini-funds.

Connect with Silvia 

LinkedIn

Stuff We Reference

Know someone who would enjoy this episode? Share it with them!

P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts.

Want more?

Connect with Andrew

LinkedIn | X | Angel Ops E-Book

All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

Silvia Mah: [00:00:00] You gotta have that muscle memory of what your thesis is.

Andrew Kazlow: Practice, practice, practice. 

Silvia Mah: You take that piece of your heart and you say, yes, and I will write that check.

And she'll think about us at the exit because we've always been there for her.

Trust is the most valuable currency of the angel investment world.

There's three Cs of capital, financial capital, experiential capital, and network capital. And usually there's one student that always says, and we die.

Andrew Kazlow: Welcome to the Diligent Observer, the first podcast exclusively focused on helping angels see what others miss. I'm your host, Andrew, and every week we explore what works, what doesn't, and why through conversations with experienced startup investors and operators.

 My guest today is Dr. Silvia Mah, who is backed over 160 startups with diverse founding teams. As the chairwoman of Stella Foundation and a founding member of the Stella Angels, Dr. Mah is revolutionizing how female investors approach early stage investing. In this episode, we discuss the dramatic rise in angel funding for women-led [00:01:00] startups, her work building university entrepreneurship programs, and her practical frameworks for finding hidden investment opportunities.

I hope you enjoy learning from Dr. Mah as much as I did.

One quick note before we jump in. If you're an angel investor or thinking about becoming one, you need to know about the Angel Capital Association. The ACA is an incredible community for connecting with experienced investors, tapping into tons of well-documented best practices and training resources, and just generally keeping up to speed with what's happening in the angel space.

Now I've really enjoyed getting connected over the last few years and that's why I'm so excited to partner with the ACA to bring you this special series of episodes live from their annual summit in Denver. If you're serious about angel investing, you will definitely want to check them out. Silvia, thank you for being with me today. 

Silvia Mah: Thank you for having me. 

Andrew Kazlow: So, we are here on day 3 of the Angel Capital Association Annual Summit [00:02:00] in Denver, Colorado.

And it has been a whirlwind of a few days. We're thrilled to be here today with you.

Silvia Mah: Yeah.

Andrew Kazlow: Dr. Mah and I would love to hear as a starting point. My favorite first question. What are you excited about right now? 

Silvia Mah: Well, I'm excited that we're here in Denver. It has been a really, a great place to meet with people.

It's centralized in the United States, so we've had really great angel groups that come out. And we had great conversations. We've had individual angels come and be curious about this asset class. And then of course, hearing from the leaders of the leaders, on stage and hearing from really insightful panels.

Andrew Kazlow: Well Share maybe some nuggets from the week. What are some of your key takeaways, things that you'll go home with that you learned this week? 

Silvia Mah: A couple of things. One is there was a keynote at lunch, with a female founder, right. and she was talking about what it means to be a founder.

It means a lot of heart, a lot of resilience, but that matches with that the investor who [00:03:00] needs to have the resilience to, let's say invest at a really really risky asset class and have that piece of investing in that entrepreneur, believing in that entrepreneur and that have that entrepreneur scale as she has scaled so incredible.

The second thing is that we had a really great panel discussion on AI, right? So how do angel groups actually use AI? That we separated out into a couple of different groups of things. So one was more like sourcing and how do I do reports? How do I do due diligence? And then also like interaction with accelerators.

And one was, the reporting and the sourcing and making sure that we have deal memos. Who writes deal memos all the time, angels, right? Angel group leaders. Perplexity is one that a lot of people use. Of course, like Gamma AI to be able to have PowerPoints that are easy to create and to share.

Andrew Kazlow: Well, any use cases or any.

Silvia Mah: Yeah.

Andrew Kazlow: Before you move to your thread, any AI like applications that [00:04:00] surprised you or that were like, whoa, I didn't think about that. 

Silvia Mah: Yeah, no, I use AI a lot. And so, at Biola University where I'm a professor at, we have an AI lab, so we really dive into how do we use AI for good.

What we heard was and I do do this, it's basically taking all the information that we have from entrepreneurs, and this is coming from Ohio State University. So she goes, look, I'm a one-person person show, and it's a lot of angel groups are like that. Right? Am I right? 

Andrew Kazlow: Yeah. 

Silvia Mah: She basically takes all the information that she has and basically puts it in Perplexity and says, this is how my template needs to be.

I need to have this information. She has it all in a Word document that she puts into the prompt and be able to say, okay, I need it to look like this. And then it spits out and then it's like, I need this evaluation to happen. And she has it all prescripted based on her investment thesis. So it's like she has that Word document, she puts in about four or five of these prompts, gets that information from Perplexity based on the documents that she has from entrepreneurs.

So that's a really easy way for her to [00:05:00] do an investment memo a lot faster, right?

Andrew Kazlow: And anybody that's listening, I mean, you could spin that up. 

Silvia Mah: And anything 

Andrew Kazlow: And a few hours.

Silvia Mah: Mm-hmm.

Andrew Kazlow: Sitting down, you know, custom GPT or a Claude project or pick your favorite

Silvia Mah: Yeah.

Andrew Kazlow: Tool and Perplexity. You can work with Grok, different flavors.

Silvia Mah: What I liked too was TCA, Tech Coast Angels, Orange County, they use that, but then they also use that first base memo to be able to create a due diligence team that has a project plan for the next three weeks for them to go through. If I have this memo, what would be my project plan for three weeks with five members on the team?

 It automatically creates this schedule, per se, so that you can really be more efficient with the volunteers that you have for your due diligence teams as an angel investment group. Those were two pieces that I'm like, oh, interesting. Templates work. You can prompt it correctly. And then secondly, project planning so that you can have your investors work on what they love to do. Right?

Is go [00:06:00] into due diligence, but not worry about how do I implement that? What is my schedule of things to do? 

My third nugget was that, we had a VC specific keynote, and then we had an angel specific keynote.

So VCs were more the VC gentleman that's Ilya from Stanford University. He was focused on unicorns, right? What kind of universities are the top universities that put out founders that become unicorns. A lot of people didn't like that because it's a little bit of like, well, we don't invest in the unicorns all the time as angels.

We want really great returns, obviously. But that is not, let's say something that we're consistently looking at having a whole portfolio of unicorns. And then we had another one that was an angel specific of going after the founder and the startup that is about heart and about resilience and grit of that entrepreneur and investing in that team, but really understanding what the markets are in this and that so that you can have the return that you want as an angel group.

So those two were kind of dipoles. What I [00:07:00] loved about it was that within this summit, we were having better conversations about how we do things as angels. Like, how do we evaluate companies better? Do we actually want the unicorn or we don't want the unicorn? Do we wanna be more impact specific? So we had those great conversations when you had an event that gave you two very disparate pieces of data and two different leaders that give you that information. So that's a really great tip for anybody who's like working on an angel event in their ecosystem. Don't be scared about having two very different ideas. Being put on stage because you have richer conversations in the smaller rooms, the networking and all of that.

Andrew Kazlow: Silvia, I love that point. You know, It's so common for newer newer investors, or even just in general interest parties when they get connected to this ecosystem to think, oh yeah, angel investing and VC like that. That's all the same stuff, right? But [00:08:00] we're in a room of people that traveled from wherever they traveled from to be a part of the Angel Capital Association event.

They care about angel investing, and many in this room understand how different angel investing and VC is. But I think it's so important that we're highlighting, yeah, there's significant differences, and yet we are related. We are often in on the same deals, and so we need to understand as angels, how VC works and then vice versa.

Many VCs are reliant on angles to help serve as a conveyor belt, so to speak. To help move companies along to the point where they can be a fit for the venture thesis. So, uh, It has been a blast to see that conversation mature, just like you shared.

Silvia Mah: Yeah. Love it. 

Andrew Kazlow: What else? Any other takeaways, any other things that you'll take home. 

Silvia Mah: Well, One of the takeaways of course, I'm a gender lens investor. I invest in women-led businesses and I also co-invest and syndicate with other female angel groups. So we had represented here, of course, Stella Angels. Where Stella Foundation is what I have led for the last 15 [00:09:00] years and we have an angel group.

We've had Next Wave Impact here, fund. And that's been a fund around for about seven years. That is impact and women founders, we have Golden Seeds. The tried and true legends, right? Um, That have invested in female founders with investors that are male and female. We've had so many wonderful groups.

Citrine Angels has really great groups that come together to talk about how do we invest better, into female founders. And again, like a lot of people think it's only female angel investors that invest in female entrepreneurs. And that is not all the way true. And the other thing that we were talking about in the Women's Capital Call, Women's Capital Group Breakfast. I got it right finally. We also have a Women's Capital Call at ACA. We have it every single month. So we were able to share deals and stuff like that. So what we talked about in the breakfast was that the, the data that we have from VCs obviously is from, let's say, PitchBook and Crunchbase and all of that.

So yes, we are at 2% of [00:10:00] VC funding going to very specifically to female-led or female founded startups. Now, if you take the data and that the data is 2024. Right? From all the VCs, is that actually whenever you have a co-founding team that has a male and a female, so it is a mixed gender founding team, you're up at about 30, 35% of VC money going to those types of startups. So we're trying to see like, how do we change that? Because

everybody's like, oh, this hasn't changed in how many years? Well, it actually has, It's a movement towards something that we wanna make sure that we have great information on. Well, the angel investment world, which is earlier. Right?

So VCs are usually seed series A.

Andrew Kazlow: Yep.

Silvia Mah: We're looking at pre-seed seed angel investing. We have data going back to 2023. It's a lot harder to get angel data than VC data. So that's one thing that everybody should know is that it's a lot harder to get it from angels. 

Andrew Kazlow: Yeah, we just had John [00:11:00] Harbison and all who's been pioneering data collection and analysis across TCA as well as a number of other agencies.

Silvia Mah: Angel Capital association. Yeah. We do a whole data call and we have wonderful reports that allow angel investors to make better decisions because if you have that data, you can make better decisions.

Andrew Kazlow: Yes.

Silvia Mah: So going back to the data on female founders in 2023, we have that information.

We're about 40% of all angel deals that angels have invested in go-to female-led teams. 

Andrew Kazlow: Wow.

Silvia Mah: So you see, and it was about 2% to 3% about 10 years ago.

Andrew Kazlow: That's just incredible.

Silvia Mah: That's incredible. That is what the power of networks, that's the outcome of those networks and those angel networks that really pour into entrepreneurs in their ecosystems to actually invest and grow.

Andrew Kazlow: Amazing.

Silvia Mah: Yeah.

Andrew Kazlow: Well, Let's talk more about. You mentioned ecosystems. Mm-hmm. And that's something that you've been deeply involved in, particularly in the university space, helping have [00:12:00] university entrepreneurship communities grow. I mean, that is not a simple thing to do. It's easy to say, right? Oh yeah. We need a thriving entrepreneurship ecosystem attached to our university. Great. How do we make that happen?

 we've got some that's just natural, some that's organic. Maybe there's programs in the past. Talk us through the work that you're doing with university programs and then maybe specifically for the listener that's an active angel. They're obviously affiliated with some university or have some connections.

How might they best put their shoulder to the plow, so to speak. 

Silvia Mah: Yeah, I love that question. So mostly whenever I'm talking to angel investors that are asking that question, how do I get involved in earlier stage companies, especially around universities, I always say get partnered up with a university a in your ecosystem.

So if you're geographically in the location like I'm from San Diego, get involved with pitch competitions in your ecosystem. So San Diego would be UC, San Diego. We have pitch competitions at USD, San Diego State University. [00:13:00] Get involved, get active, so that you can actually see those founders and those startups and be able to invest individually.

And then there are some universities that have alumni funds. I can go into like what? There's a whole like me list of things that people do. But that's one thing. But then the second piece of anybody who wants to get involved in university innovation is go back to your alma mater. Right? Is saying, do they have an alumni group that invest individually?

Do they have a fund, do they have a pitch competition that you can get involved with so that you can learn more about it? Go back to that. And we're finding, I'm a professor at Biola University and Director of Innovation at Biola University. That's That's the Bible Institute of LA. So a lot of people don't know that.

Andrew Kazlow: And I didn't know that either. I love it.

Silvia Mah: Yes. Up in Orange County. And really, we rely on our alumni to come back and mentor, advise our student entrepreneurs. So We have a startup competition every single year. So, um, Around the April timeframe. And what's interesting is that we [00:14:00] have mentors and who are also investors that come in, talk to the students. They might be judges of pitch competitions and they have invested individually, right?

We do not have an alumni fund, however, we're looking at incorporating a, a let's say tried and true practice called the Angel Conferences. It started off in Seattle. So, Seattle Angel Conference. It's an event fund that goes for about three months to be able to bring in aspiring angel investors and existing investors together to invest in, let's say, a pitch competition type of thing at the.

And you have about six finalists that you do due diligence together and then you invest in the winner. Typically the winner gets a hundred, $200,000. So we're bringing that to Biola University so that we can actually activate angels in our community, alumni or mentors and advisors that have been part of our ecosystem to be able to work together, to invest in entrepreneurs that are part of the Biola University ecosystem.

Andrew Kazlow: So you guys spin up an SPV of some [00:15:00] sort, or how do you manage that fund? 

Silvia Mah: Yeah. It's a mini fund basically. 

I love it. 

Andrew Kazlow: And these are happening in a number of places, you said?

Silvia Mah: Yes, yes. In Seattle, but 

Andrew Kazlow: there's, 

Silvia Mah: there's 

Fresno, there's Alaska, there is San Luis Obispo. There is, yeah.

Seattle and San Diego.

Andrew Kazlow: Wow. Does each university manage this themselves, or how does that work?

Silvia Mah: Oh, great question. No, I was just saying as a confluence of my own ecosystem and where I'm at, being at the Director of Innovation at a university, I'm looking at bringing in the Angel Conference model to do the Biola Angel Conference. Now, University of San Diego

has the San Diego Angel Conference. So they used to have it for about six years now. It transferred to San Diego State University for San Diego Angel Conference. So that's why we didn't call it a specific university. It's more of the community coming together and being part of the Angel Conference.

But we find that typically if you're connected to a university, you get to do all the information sessions, all the events and all of that at a university that brings in [00:16:00] alumni, that brings in an alumni community at University of San Diego. Actually, we created a fund for people who wanted to invest in more deals after they got the education at San Diego Angel Conference.

Andrew Kazlow: So, let me ask you a question that many of our listeners might be thinking.

Silvia Mah: Yeah.

Andrew Kazlow: There's a lot of entrepreneurship programs even within the same university ecosystem. Entrepreneurship is hot. Being an angel investor is cool. There is a lot of places to get plugged in and if I want to get plugged into. 

Name a university's entrepreneurship ecosystem. There's 14 different ways I could do that. I could co-teach, I could come to one group's pitch event, I could come to some other group's pitch event, like there's almost these competitive I think it's all good, but there's just a lot of places for me to spend my time.

So, what would you coach a investor who's eager to plug in, but it's just I don't even know where to start. I don't know where my energy is best [00:17:00] placed because they may only have a few hours a quarter to allocate to this and wanna use those wisely. What's your decision framework for picking the most value creative, value additive space to throw that shoulder to the plow? 

Silvia Mah: Yeah. I think that some investors are already plugged into their ecosystem. They're either economic development people or they're part of a university because they love working with students. I would say take that first plunge and you can invest in a company that you are excited about, that you wanna learn more about.

Of course, do your due diligence, right? The ACA reports always say that you should do more than 40 hours of due diligence before you make that decision as an individual or as a group. But I do a lot of due diligence just so that I can make better decisions. So first of all, if you're already active in your ecosystem,

take that plunge and write that first check. 'Cause as soon as you write that first check, I know that's a huge lean in.

Andrew Kazlow: Yeah.

Silvia Mah: But some people are that close. So I just wanna [00:18:00] encourage anybody who's that close write a check. Secondly, as the ones that are a little bit still on the fence, they're looking at everything, they might be involved, they might not be involved.

I would say go one step further and ask more critical questions. Have coffee meetings with entrepreneurs. See how you can learn more about what they're doing. And I always recommend in that first year of going into saying, I am an angel investor. Go in and join a group. Because you learn so much from each other.

For us at Stella Angels, we really want female investors to come in. We have lots of virtual opportunities to just hear pitches. And if you wanna have that deeper conversation, come and talk to us. Send us an email and then we continue to shepherd you through that journey of being an angel investor.

Because to grow that angel community for yourself, it's all about trust and relationships. Trust is the most valuable currency of the angel investment [00:19:00] world, and that stands for tremendous reciprocity between you and us with sincerity and transparency.

Transparency is super important.

Sincerity is super important. And how do you build that? Is to join and be in community with others. 

Andrew Kazlow: Mm. So tell, Tell us more about your work as an educator.

Silvia Mah: Yeah.

Andrew Kazlow: Say more about what you teach, and maybe what some of the most common preconceptions you break during your classes. 

Silvia Mah: I break everything.

Kind of going with that same theme of trust as a professor of entrepreneurship and innovation, having a student come in with this idea, they're a little bit like worried. They're like, is my pretty like idea pretty enough for you? So I never say it's not, it's an ugly thing. I say, why have you done this?

What have you done as research? What's going on? What is traction that you're done? Oh, I don't know what attraction means. I'm like, okay, do some customer interviews. Going back to Steve [00:20:00] Blanks, lean methodology. So enabling a student in a university to go down that curiosity route or that creativity route is so important and how I've created

a way to help them through that. So we have a course obviously at Biola and I lead it, is an entrepreneurship practicum course, and we really go through doing a vision board first. We do customer interviews, we have ideation sessions of mind maps and all of that. We do business model canvas.

We do value proposition, canvas, they pitch right? And every single, so that's like the whole path of that curriculum, but every single day I have them pitch their idea wherever it is. So, that muscle memory allows them to know at the very end they can pitch anything about that idea because they've done that muscle memory all the way through that semester.

Secondly is having creative sessions at the very beginning of my class. So I take 15 minutes to have them be creative and that allows their minds to think creatively. And then it [00:21:00] opens it up to this idea that they're a little bit scared about. So they've opened up their creativity, then they put in their idea and they're more open to be more creative within their idea that they're worried about.

One of them is, giving them a prompt saying, I created a rocket ship and I'm going to the moon. Now you need to write a one-pager of what your journey is to go to the moon. So, they have about five minutes to just write on a piece of paper, as much information as they want the journey.

It goes crazy sometimes. They're like, and I became a cow and I'm a purple cow and I'm like this and I go to, and it's just beautiful. And you get to know everybody's individual flavors. That pedagogy of writing something allows them to transfer everything in their brain to paper. Secondly is I give them another creative brief, basically is giving them a picture of a pencil.

And I said, how are the multiple ways that you can use this pencil? And they're like to write, I might go fast, go deeper, come on. And then the next picture is a laptop. So what are the other uses of a laptop? So that's [00:22:00] convex and concave kind of creativity. So that they're looking at how do I open up.

That's convex going open saying like how many things that I can do for that. And convex is more of like, how do I bring it together? Saying, okay, if the laptop does Um, Google and this and that. How, What could it be that is a simpler form of that. It could actually be a paperweight. So that's how we go and that's the pedagogy behind that.

So that's in a class. You can do that framework that everybody knows is Steve Blank framework, muscle memory, and then these creative sessions at the very beginning to open up their minds. 

Andrew Kazlow: So I walk into class, I have to pitch my idea.

Silvia Mah: Yeah.

Andrew Kazlow: In whatever form it is. I get this creativity juice 

Every time.

Juicing, every time I sit down 

and then we start the class. Yeah. That's so fun. 

Silvia Mah: Yeah. And then at the end of class we do a "Yes and..."

Andrew Kazlow: Ah, so that's improv.

Silvia Mah: That's improv.

Andrew Kazlow: Yep. Right.

Silvia Mah: So, I do it for two and a half hours. Every class I have two and a half hours. But you could do it in 45 minutes.

And the "Yes, and..." is very exciting because it's like I say, okay, today the leaves are [00:23:00] falling 'cause it's fall, yes, and...

Andrew Kazlow: Yes, and...

Silvia Mah: And usually there's one student that always says, and we die. It's always like, but you get everybody's personality so that you really become a community. Right?

So you're talking about your ideas, you're being a little bit vulnerable with a "Yes, and..." a little bit vulnerable about the creativity, but you're creating this community at the end, we have dinner for finals. The final exam is a dinner networking. 

Andrew Kazlow: Beautiful.

Silvia Mah: So, that's just one course that I teach.

Andrew Kazlow: So tell me, what is the angel investor equivalent of this class?

How do we do this with our investment community as well? Because I think there's so much value in flexing these muscles that maybe we don't as often. I think it's easy as an angel to sit down and. We talk a lot about innovation and we get excited about innovation and if we're plugged into the angel ecosystem, like obviously we're choosing that there's a million things that any of us could be doing with our time and our capital, but we're choosing to participate in this asset class.

For one reason or another. But a lot of us, we just love it and we want to give back to the [00:24:00] ecosystem and yet, I feel, I still think it can be easy for many of us to get locked into our patterns of this is the kind of thing that I'm looking for and, oh no, you're outside. I'm out. Without really flexing those creative juices, discipline, rigor, consistency, super important.

And yet, we're in the outlier business. And yeah, maybe not every investment's gonna, most investments won't turn into a unicorn, but it'd be great if we had a unicorn. All of us would love to have unicorn in our portfolios, and that's what's gonna return this whole thing. And so outliers tend to be weird.

They tend to not fit in the buckets super easily. So just riff for me, like what, yeah. what does it look like to do this, maybe it's happening today, maybe it's not, but it should be. How are we doing this with our angel community? Because you think taking this framework, this way of thinking is so important.

Silvia Mah: Yeah. So I have answers to all of those things. 'Cause I do this all the time. So I do have a book, the Startup Investor Mindset on Amazon. I go through, let's say, how do you get into your community? How do you do coffee meetings [00:25:00] and all of that. So that's tried and true. So I would say the same sort of thing.

You have this process, you probably heard as an angel investor, what your due diligence checklist is. You know that the five M's of investing are this, you have all of these kind of parameters that you're taking a course. From Angel Capital Association, obviously we have Angel University that you can take all these courses on demand now. You have on demand courses from like 37 Angels, from Golden Seeds, from all these types of angel opportunities to learn. That's how I learned. Think about it as a course. You're always learning, you're always curious of learning. Then the aspect of that curiosity and that creativity. You're basically going to pitch competition and saying, okay, wow, this pitch, what is it? I would highlight that after any pitch competition, you should actually write in a journal saying, I really like this one because of these things. I like this 'cause then that allows you to be creative of what can you do for them or what did you learn from that?

And then the bookend of "Yes, and..." would be the follow on conversation right? Is have lots of [00:26:00] coffee meetings with entrepreneurs and investors. So as you said, like how do we find the outliers? Is that if you are curious about, and a startup don't be about like fear of missing out, FOMO or like somebody else's investing and I shouldn't, or I should, it's more of

I'm curious about this startup. Let me take them out to coffee and learn a lot and ask curious questions. I always say the "Yes, and..." of oh, how is your company? You're like, da, da, da. Oh, yes, and what about this da da da. Well, yes, and what about that? That's the like the seven why analysis is the same sort of thing to get the root cross, similar types of thing.

Do that in a coffee meeting. Similarly, I always tell in investors to do the same thing to another investor. Go out to coffee with another investor that's in your ecosystem or who is fundamentally different than you. Right? That's how we get to those outliers. That's how we pull that bell-shaped curve out to understand what's on the outside 'cause you know your thesis.

And lastly is, in my book I talk about creating your investment thesis. A [00:27:00] lot of individual angels that even join a angel group, they are wishy-washy of what their thesis is.

Andrew Kazlow: Yep.

Silvia Mah: Spend the time just to write it out. And then test it. Saying like, why am I interested in that?

Why am I so focused on that or what makes me joyful or what brings purpose to me? What am I blessed by? The founders that have been part of my portfolio, does that align to my thesis? And then talk to another investor saying, what is your thesis? And then as they're talking about it, you are pitching them your thesis.

So that's the reverse pitch. So it's that muscle memory that I was talking about in my class. I say the same thing to investors. You gotta have that muscle memory of what your thesis is.

Andrew Kazlow: Practice, practice, practice. 

Silvia Mah: Practice. Because then you become more clearer and also you became more creative saying like, I really care about this.

Are you in this thesis? Let me talk to you a little bit more. You find the outliers and you found the ones in your bell shaped curve. 

Andrew Kazlow: And I think that's one of the most exciting things about the Angel Group, is that the Vanilla Angel Network, you know, [00:28:00] let's not consider funds or

yeah, 

Silvia Mah: yeah. Angel Network.

Yeah. 

Andrew Kazlow: Complex strategies.

Silvia Mah: Yeah.

Andrew Kazlow: Traditional Angel Network is a collection of 50 or 100 people that are all coming together around a general theme or a general focus, but each one of them has their own personal strategy, their own experience, their own thesis, and they're building different portfolios.

Not every angel is gonna invest in every deal that gets funded by that group, and so I think that's one of the most, all at once convoluted and yet fascinating things.

Silvia Mah: Yeah.

Andrew Kazlow: About the angel space is that, an angel group is a connection point for a bunch of different entrepreneurs, a bunch of different angels, all of whom might be a fit for one another.

And there's just so much opportunity to learn from people with very different strategies. I love this concept of just cultivate curiosity.

Silvia Mah: Yes.

Andrew Kazlow: And that will serve you very well. 

Silvia Mah: Yeah, and on both sides of you growing your angel investment network and what you care about and who you wanna connect with,

'cause that leads to better syndication.

Andrew Kazlow: Yes.

Silvia Mah: That leads to better partnerships. I co-invest with so many wonderful female investors 'cause [00:29:00] I know exactly what they go after, 'cause we've had great conversations and then they can bring their expertise into that portfolio company. And that portfolio company actually scales and does really great.

So that's that beautiful piece of keeping curious, keeping educated, connecting with your community, early and often, and going after all of those things. 

Andrew Kazlow: Silvia, final thoughts for our audience as we wrap up? 

Silvia Mah: Oh gosh, there's so many. It's just been a joy to be part of this. So thank you for having me come onto the podcast and showing, sharing some wisdom.

I think one of the things that a lot of angel investors have a, let's say wall per se is that they have to be perfect. They need to create the perfect portfolio. It has to make this amount. You are gonna make errors and decisions that are not gonna be the best. But at the time that you invest, you have made the best decision that you can with all the information that you have amassed from really,

like you said, very rigorous data analysis or, due diligence [00:30:00] and like you've talked to all the people that you can in your network. You've talked to the entrepreneurs so many times that you're so passionate about that entrepreneur making it, you've done all the decisions that you can, and you make that decision because of all the data that you have in place.

And you take that piece of your heart and you say, yes, and I will write that check, right? Because that allows you to grow a portfolio that you're proud of. That you can talk about that you have great stories about. We were just talking about in a panel, one of the stories of one of my exits.

So it's Uqora, it's a UTI prevention drink mix. And they sold to Pharmavite. And that is the creators of nature made vitamins. So, what's interesting is that this is a femtech company that went through our accelerator. I invested in her as an individual angel. I co-invested with other angels.

I brought her to Stella Angels. I brought her to my VC fund, called Astro Ventures. All of us invested in her. She stayed with just one more round past us because she was building on revenue. So [00:31:00] amazing and about seven years later she was able to exit. We helped her with the exit communications and how to think about that.

But that exit partner wanted her whole entire team to create, and start creating a femtech division of Pharmavite. Right? So that was very important as investors to pour into this founder who's exceptional and done so, so well. And then be able to have that go into the exit deal that is ideal.

So that's why it's so important when you make those decisions and you're like, I love this founder. I've made all these possibilities done. I've done all the due diligence. I bring everybody together to invest because I believe in her. She will continue to scale and exit correctly and very profitably.

And she'll think about us at the exit because we've always been there for her and she's always been there for her customers. 'Cause she's blessing her customers with an incredible product to prevent UTIs. Hello. So those are the kinds of things that when you make those decisions very [00:32:00] purposefully and you write that check, you never look back.

You build a portfolio that you absolutely are proud of. And yes, you might have them that fail. That's okay. 'cause you've learned. 

Andrew Kazlow: So I have to ask, can you give me an example of a check that you wrote that ultimately did fail? 

Silvia Mah: Yeah, lots of them.

Andrew Kazlow: Where the same policy tries true. Because I think so many conversations, it's so much more fun

to talk about the winners.

Silvia Mah: Yes.

Andrew Kazlow: Tell me about, a founder that you backed, you made that commitment and they ultimately were a zero for your portfolio, but not for your broader kind of humanity. 

Silvia Mah: There's definitely one, and I'm not gonna mention her name just because I don't know if this is something she wants to share.

Obviously it's a female founder in the CPG space. Not that I only invest in CPG, I have a PhD in Biochemistry, love deep tech, right? So this is another CPG company, but really was able to invest in her. I love the check that I wrote. I did all the due diligence that I can. She did go through San Diego Angel Conference and we had a lot of investors that were excited about her.

Wonderful investors that loved what she was doing. She was scaling [00:33:00] through revenue. She had three sites of what she was doing, scale, scale, scale, really great. Something just hit her on the side and broke the company. Like we heard in a keynote of one of the entrepreneurs that is like, you're, go, go, go, go.

And then you hit that wall and you're like, what just happened? That's what happened to her, and she had a closeout. But even in the closeout month, I was talking to her. I was like, what are you doing? She goes, I care about my team. I care about the product that we built. I care about this.

I care about my investors. How can I do this in light of the investors? She did not just say, okay, I'm not going to interact with you. She was really interacting with us, communicating with us, saying, this is where I'm at and I have to close. Even in that process, she came back to us and asked us for that support, and we helped her through that.

We connected her with lawyers that helped her through that, bankruptcy attorneys, all of that. We helped her get through that because we knew that all of us had to not win. Obviously, we were losing our investment, but that everything was pushed [00:34:00] through in the most appropriate way.

That was good for the company, for the investors, and the founder. It was just an unforeseen circumstance that nobody saw coming. 

Andrew Kazlow: I love the theme that you're highlighting with these two stories, and that is this concept of how the dollars are important, but the relationship is more.

Silvia Mah: Yeah,

Andrew Kazlow: and the value that an angel is able to add in terms of ongoing support, making introductions, even connecting to the right lawyers.

Silvia Mah: Yeah, yeah. 

Andrew Kazlow: These are the things that entrepreneurs don't have the time to think about. They're running a million miles an hour doing more than they should be, making less than they should be trying to run families.

Like it's too much. And so I think it's just so encouraging to hear the way that you've done this for many A founder.

Silvia Mah: Yeah.

Andrew Kazlow: In recent years it seems. To come alongside and provide more than just capital. And for those of you who may be listening to this that are like, I just don't have the time for that.

I don't have the budget for that. That's amazing. Find someone like this 

Silvia Mah: and other people too. There's so many people

Andrew Kazlow: and other wonderful general partners who are able to allocate those dollars on your behalf as an LP to [00:35:00] deploy those, cap those dollars and add value to the entrepreneurs that they're partnering with.

Yeah. It's so important. 

I always say that 

Silvia Mah: there's three Cs of capital, financial capital, experiential capital, and network capital. 

Andrew Kazlow: So whenever you're. Conversing with that co-investor or that entrepreneur. You're like, I can give you money. I can invest this dollar amount, but I can also bring my network along and my network might be two or three people.

Like for those early stage investors, that might be all that they need. That's a beautiful, wonderful thing. And then that expertise, maybe you have been in, let's say, Intel forever and you're a technologist and you can bring that expertise onto the team. That's fantastic. Or you know somebody who does. So it doesn't mean that you have to have this huge network of people, but those three pieces of capital are so important for any founder to leapfrog into scalability and then obviously exit that we all want.

Fantastic. Silvia, we will wrap there. Thank you so much for joining me today. Thanks for listening to this episode of The Diligent Observer. I'm your host, Andrew, and if you're an angel investor looking for essential angel intel in five minutes every [00:36:00] week, I think you'd enjoy my newsletter. I send my best stuff, interesting deals, and more straight to your inbox so you never miss a thing.

Subscribe today@thediligentobserver.com.

People on this episode