Angela Jackson on her approach to investing through empirical evidence and diversity at the decision-making table

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In this episode, Elias Rubel is joined by Angela Jackson from Portland Seed Fund. Portland Seed Fund invests in the most talented entrepreneurs in the region, those capable of building high-growth, capital-efficient companies in a variety of sectors. They operate a non-resident business accelerator program designed to connect entrepreneurs with Oregon’s growing startup ecosystem, from mentors and advisers to capital, customers and employees. They are committed to supporting their portfolio companies and helping them reach their potential.

Episode Outline

[04:39] Angela’s background

[07:16] How does sales and marketing operationalize their work

[10:13] The ability to be more creative and more agile with more of your execution moving forward.

[11:18] Early risk taking that you can model

[12:04] Technical founders who are creating product to solve kind of niche-y problems

[14:34] To be a good investor, you have to be willing to be wrong

[16:35] How to embrace a more diverse set of perspectives at the decision-making table

[17:04] Will she invest in purely technical co-founders?

[19:22] Use empirical evidence to decide what, what the best option is moving forward

Anglea's Inspirations:

Lucille Ball

Carol Burnett

her parents

Connect with Angela:

Portland Seed Fund



Elias Rubel (00:32):

So today I'm super excited to welcome a good friend and someone who's been really instrumental in my own professional career. Maybe one of the most instrumental figures in my professional career as the first institutional investor to believe in me as a founder and right that first, the first venture check I ever deposited actually Angela has more than 15 years experience as a venture capitalist. She co founded the Portland seed fund. She serves as the managing director of Portland state university center for entrepreneurship and manager of the Portland state business accelerator. Angela Jackson, welcome to the show.

Angela Jackson (01:09):

Thank you, Eli.

Elias Rubel (01:11):

Great to be here. So I always love to start with the kind of origin stories and I know from having had many after working session beers with you that you grew up in a family of entrepreneurs. So I would love to just take a second to hear that story and, and understand, and maybe ask how you think growing up in an entrepreneurial entrepreneurial family has influenced your career.

Angela Jackson (01:41):

Thanks for asking that because it's a, it's one of my favorite, thanks to think about and talk about, you know, when you're a kid, you don't think your life is any different than anyone else's, and it's not really till you're a lot older that you look back and realize, you know, what, not everyone sat at the dinner table and talked about the company that my parents were starting, or, you know it was a very different perspective and I think it comes down to risk appetite. I didn't realize it at the time, but my family always had everything on the line with the family business and very much saw running a business as a privilege and a humble opportunity to help grow well, not just with our own family, but all the people that worked with and for the company and those lessons are really embedded in how I see business today and what motivates me. It's it's not all about money. I mean, money is a reflection of what follows when you do a lot of things, right? Mmm. But most people who end up getting rich there, they're chasing a mission or a movement and not so much money, money just happens along the, and that was a core value. And I very much remember those conversations and that risk appetite growing up like that.

Elias Rubel (03:10):

Sure. And so, I mean, at this point, just to flash forward for listeners who are catching up on your story, I mean, you've had how many exits now with the Portland seed fund in an incredibly short period of time?

Angela Jackson (03:23):

Yeah, we've been very fortunate. I think that 2010 was when we started investing with Cortland seed fund and as a timing check, we were coming out of the great recession and there were a lot of entrepreneurs getting started and valuations were good at this point. We've had more than 20 creative exits. And by that, I mean, I'm only counting the ones that have at least returned capital we've done better than return capital. Otherwise you don't make it as a, as an investor all the way up to sort of mid, mid, double digit exits multiples rather on exit. And of course, as you know, with this very early stage investing a lot of exits come by way of failure. And we've certainly had our share of failures as well. I never liked to hear seed or early stage investors say that they haven't had any failure yet because that's the wrong asset class. Their failure comes with this very early risk-taking and you can model so that you offset taking extraordinary risks with extraordinary gain. But you know, to say, Mmm, we haven't had an issue or a failure yet is just, you know, that's, that's more of a main street or PE kind of, I thought.

Elias Rubel (04:55):

Sure. So I'd love to dig into that. I mean, as you know, the, the purpose of the show here is to take for stories that uncover patterns from that initial sprint, going from 1 million in ARR to 10 million and beyond, and chatting with investors and operators who have seen these play out time and time again. And, and so, you know, you begin to establish some really good pattern matching both in what works and what doesn't work. So maybe rather than starting with what you've seen work, it would be really fascinating to flip the script and start with patterns that you've seen play out that almost always have led to the ones that didn't work out. And then, and then we can talk about the fun ones that did

Angela Jackson (05:39):

That sounds great. You know, it's interesting. I knew what we were going to talk about, and I, I looked back over the early portfolio and we invested in a lot of SAS early on. So I am curious as to why we're seeing as a ratio, fewer SAS deals. We could prognosticate about that later if you want, but as I look through that early list many of them were just what you described, not big winners. They exited, they found an exit a home, but there was, you know, it was more of a, you know, a survival play or a, you know, a rescue. And if you, again, you can almost chart our investment arc from recovery, some of those early, early exits closer to 2010, we're what we would call acquihires. And those don't often come at the highest multiples, but at the same time, you're glad to see the team.

Angela Jackson (06:43):

Mmm. You know, have a soft landing, get a new home their packages, their employment packages are good. And you like to see that but the return for the investor on some of those wasn't so hot. And I think as I look back on what characterized some of those early investments, and why did they go the way they did? I think, you know, one of the trends was that they were largely technical founders who are creating product to solve kind of niche-y problems. And they believed, and I guess we believe to where we wouldn't have written the check that somehow that could transform into something more catalytic with high velocity growth that Mmm. You know, it could be a super promising SAS business but many of those early investments. And I'm here looking at a list of about 12 of them that, you know, great founders, very earnest, their primary skillset was technical product making. Mmm. But they probably lacked any ability to jump houses into another functional area in the company. They resisted sales, they resisted marketing, they resisted boards or they resisted having, you know, even someone come in and do the books. So that looking back as a pattern. Mmm. Yeah. I can already tell in how we've changed up our investing by fund three now that we we've learned from, and we're, we're jumping into fewer of those deals.

Speaker 4 (08:26):

So that's really interesting. Now, if we take the inverse of that net year in fund three, it sounds like you are partnering then are looking for founders and early operating teams who either have those functional roles filled out already, or, or the openness too. Like, how do you, how do you begin to look for that?

Angela Jackson (08:50):

I think that's where you get into, how do you look for a great CEO who can endure so, and Eli, I hope you don't mind if I point you out here as one of those groups.

Elias Rubel (09:05):

Well, I thank you. I'm blushing

Angela Jackson (09:07):

Capacity and capability to learn the technical side, but you also understood at the end of the day it was a sales and a marketing and a business, as well as a technical company. And you were able to bridge multiple silos of functional expertise. And increasingly I see that ability in the companies and the founders who go the distance. So it's not to say we wouldn't invest in purely technical co-founders, but now we find ourselves finding those. Who've already had the hard lesson that just as a tech team, they didn't go very far. And we've invested recently in fund three with some you know, really smart and talented successful exited tech co-founders who earlier in their careers had a couple of zeros. Mmm. And learned from that, that the, it was very important for them early on to reach across silos and bring in cofounders that had other functional skill sets. So, yeah, there's a couple of these that I'm really proud that we're in right now that I have high hopes for I hesitate to name them if that's okay. Just because I'm not sure whether they want the publicity or not, but

Elias Rubel (10:34):


Angela Jackson (10:34):

Both of them are related to fast competing and of one flavor or another of the ones I'm thinking of where they're very technical, but they had that school of hard knocks too, to broaden the team sooner.

Elias Rubel (10:48):

So I'm curious then let's, let's dig into some specifics. Are there, are there any kind of, let's say for the ones that have been great, the ones that have the team or the, or the aptitude to be cross-functional or know when to invest into certain yeah. Sales and marketing initiatives, do you have any stories of, of specific initiatives where a company made that leap or that initial step into truly becoming an organization that was beginning to scale, beginning to increase their level of sophistication. And ultimately that step took them down the path of crossing the 10 millionaire, rrr Mark.

Angela Jackson (11:34):

That's a lot. Yeah. You know, funny enough, I'm actually going to tell you a story. Okay. Embodies that. But it's about a company that proves that I was wrong. So, Mmm. And this is the thing I think, to be a good investor, you have to be willing to be wrong, and you have to acknowledge that luck is definitely a part of the game. And not a lot of people want to say that they want to say, yeah, I know how to pick them.

Angela Jackson (12:06):

The, the over 10 million AR story, I'm going to tell you is one that totally defies what I said. It's a technical, co-founder very technical, very methodically juiced the ARR very methodically with no investment in sales or marketing. Aye. Technical marketing. Yes. But demand gen yes, but not anything other than analytics and performing analytics, measuring everything and know, and I'll be damned if I'm, they did not methodically grow you know, above forecasts, two supersede, you know, several years ago now they passed the 10 million ARR Mark. But here's, here's where it does kind of come back to what I said. There was a point where they flatlined. And again, this was a company that wanted to measure everything okay. Almost ad nauseum. But they, they realized at that point, that technical founder realized that, okay, he alone his style of thinking alone. It wasn't so much that he went for a sales and marketing talent as that he recognized that his way of seeing the world needed a companion ways of seeing and through that process, I think they were able to kind of push through this this Mark, but I think, you know, the one to $10 million, it sounds like a, Oh, well, if you get one tens, not any harder, but it really is. It really is a very big gap to bridge.

Elias Rubel (13:52):

Sure. Yeah. It's a whole different ball game. So what, ultimately, Amy, you said that there was some pushing and more just methodical digging. Where was there something in particular that took them from that flat line too? Push through it?

Angela Jackson (14:11):

I, again, think that it was realizing that there, yeah. And this is normal human nature. We tend to recruit people who are just like us. Have you ever noticed that? It's like, Oh, I sure do like that. What is it about that person that makes me like them? And an outsider might see, Oh, you just hired yourself. Mmm. But sometimes those things are too close to us and we don't notice them ourselves. And somewhere in there that particular CEO, whether he had helped from an outsider or it was internal aha moment, I realized he had been hiring people who saw the world. Exactly he did. So while still, maybe not comfortable making whole investments in different functional silos actively. I started to recruit people who he may be even bristled with a little bit at first as a way to embrace a more diverse set of perspectives at the decision making table, if you will.

Speaker 4 (15:15):

Sure. So now, all right, well, this is getting interested now we're waiting into the world of bias, whether known or unknown. And I think this would be a fascinating subject to unpack, especially with, you know, the investor lens and your view on, on kind of seeing how these biases have played out as you've watched them unfold. I guess let's, I'd love to just open that up as, as a topic broadly and see where things go.

Angela Jackson (15:45):

Sure. I think pattern matching is what we're effectively talking about. Here are pattern recognition as with all complex ideas it can be a good thing or a negative thing. Pattern matching has been one of the key reasons that women and people of color I have had such a hard time getting funding for companies that could be equal in performance and potential when it comes to getting venture capital. And if you try to unpack that well, why is that our people actively biased? You know, I'm gonna, I tend to assume the best in, I assume people have more unconscious bias than active bias, but let's unpack the whole pattern recognition thing. Right. we all have heard this story the investor who made a ton of money from a guy who did a thing with the guy and this and this, and simply that there weren't as many women and people of color trying and leading companies a decade or two decades ago, the sheer numbers of entrance to try and succeed or fail were fewer. And so the pattern recognition or pattern matching odds are if that's how people are making decisions in terms of who they're funding that can be a real negative in terms of seeking out more diverse teams. And actually the way I just told this story, it was, it was in fact, the seeking of more diverse thoughts at the table that helps them to a breakthrough. So yeah, like all complexity, as soon as you make a hard rule, you go and break it. Right?

Speaker 4 (17:38):

Indeed. Yeah. So in, in 2015 we're shifting gears here in 2015, you won the woman of influence award from the Portland journal. And I know for a fact you're an inspiration and a mentor to so many people in the startup community. I'm curious who your mentors are, and maybe not even mentor mentors, a strong word. I'm curious who has been an inspiration to you in your career.

Angela Jackson (18:11):

That is a lovely question to answer. I, I have to start with my parents who we're very boundary, pushing an edgy for their time. Especially my mother whose main job was to hold it together where my father was the entrepreneur. And she would say things like, you know, half that paycheck is mine. And we would look at her and say, you're joking. What do you, what are you saying? And now I feel so bad about that because now I completely get it. But I think how she was to to lay that out there. And they were a good partnership in that regard and very successful in the end, but through lots of struggle. So they're really, I start with them, you know, my main leaders and mentors, but other people that I'm really inspired by are honestly, people who've pushed boundaries at non-obvious times.

Angela Jackson (19:09):

And I think a lot about a comedy actually and in particular comediennes women comedians who through history, we're very much like entrepreneurs. You know, they were out in a market before other people were there before it was socially acceptable Mmm. And pushing the boundaries and finding nuggets of truth that they could capitalize on. And I think of Lucille ball, I think of Carol Burnett they and others. But those were two examples of people who really inspired me to push the boundary and make my contribution, even if it may be ahead of its time, I guess.

Speaker 4 (19:57):


Angela Jackson (19:58):

I know those aren't business but I'll come at it the other way too, as a personality. You know, I come from a long line of entrepreneurs and creative people who don't want to work for corporations. So we're all very unemployable.

Speaker 4 (20:18):

I hear that.

Angela Jackson (20:19):

Yes. And, but I have sort of the personality trait, and that goes with that of also loving people and liking people to enjoy being around me. So I haven't twofold experience with pushing the boundaries sometimes I'm, you know, I'm uncomfortable with it personally with my personality versus I want to accomplish. So learning to balance those two things that for me is, as I've aged, I've gotten much more comfortable with that. But when I was younger in my career, I would, you know, be less willing to say something controversial or do something unpopular. So again, the comedians are a big inspiration to me for that reason.

Speaker 4 (21:10):

I love that oppression, that the lenses that's really refreshing. Well, Angela, this has been so meaningful to me to have you on the show to hear some of the stories that I hadn't already heard and, and revisit some of the ones that I've loved from the past our conversation. So thank you so much for taking the time. I'm sure all of our listeners are there's tremendous nuggets in there for everyone, regardless if they're an investor or an operator themselves. So thank you so much,

Angela Jackson (21:39):

Eli. I'm so honored that you asked me to do this, and I've really enjoyed catching up with you again.

Speaker 4 (21:46):