Danielle Pensack of Rightfoot

Podcast #79: Danielle Pensack of Rightfoot

Danielle Pensack headshot
Danielle Pensack of Rightfoot

On today’s episode, I’m joined by Dani Pensack, Co-Founder & CEO of Rightfoot

Rightfoot enables developers to add debt repayment to any application.

Founding stories are always unique, but Dani and Rightfoot are thus far the most interesting to date. They moved into a retirement home to test out their initial idea. Yup, a retirement home, and only one out of 150 said yes.

The idea was that high school kids could make good money by helping retirees with technical tasks like coding; the money would then go into a 529 education account.

While the initial idea didn’t pan out, it helped them to figure out their current business and gave them a life experience like no other. Dani is one of the most resourceful founders I’ve met thus far; just wait until you hear the vacation van story.

Dani and I also discussed the core problems associated with debt repayment, how debt impacts households, her time in Southeast Asia, raising capital, and much more.

If you want to sponsor an episode, come on as a guest, or sponsor one of our many digital or in-person offerings, please reach out anytime at todd@fintechnexus.com.

Without further ado, Dani Pensack, Co-Founder & CEO of Rightfoot. I hope you enjoy the show.

Episode highlights include

  • Dani’s journey to Rightfoot
  • Rightfoot’s founding story
  • Dani’s time at IBM in SE Asia
  • How Rightfoot’s API works
  • Embedded finance
  • Financial Inclusion
  • The barriers women-led startups face raising capital
  • Tips on raising capital
  • Recommended reading – The Messenger by Markus Zusak
  • And much more…

Connect with Danielle on LinkedIn

Download the PDF Transcript of Episode 79 – Danielle Pensack HERE, or read the full text version below:


Thanks for coming back for another episode of PitchIt, a fintech conversation amongst founders, investors and friends. I’m your host, Todd Anderson, Chief Content Officer of Fintech Nexus.

What we do is take a peek behind the curtain, what motivates someone to start a company, how do investors make the right bet, what do accelerators do during and help enabling the process of growing your company, how do banks think of founders. Not to mention, we try to have some fun and what you’ll see is we’ll also do some special episodes, we have some new features coming so stick with us and you’ll get all you need to know about the fintech startup landscape. 

PitchIt is really a part of a larger podcast network here at Fintech Nexus, you’ve got my colleague, Peter, our Co-Founder & Chairman for Fintech One-on-One, you can subscribe to his feed or we have our newest podcast by one of our writers, Isabelle Castro, the Fintech Coffee Break. For everything produced by Fintech Nexus, you can check out Fintech Nexus Podcast which is really our content fire hose, all shows, webinar replays, even in-person event content, not to mention, our weekly new show. 

As always, we hope that you rate the show and write a review. I try to really take, listen to feedback seriously as it helps make the show better. You can also follow the podcast and all of our podcasts on the feed of choice, whether it be Apple, Spotify, wherever you like to listen, will come directly to news@fintechnexus.com

Now, let’s get on with the show.


Todd Anderson: On today’s show, I’m joined by Danielle Pensack, Co-Founder & CEO of Rightfoot. Rightfoot enables developers to add debt repayment to any application. You know, founding stories are always unique in some way, I think Dani and Rightfoot take the cake on the most interesting founding story to date. Dani and her co-founders moved into a retirement home to test out their initial idea which was having high school kids make money by teaching the retirees technical tasks such as coding and other online tasks that they ultimately would then pay the high schoolers for. They put that money that they’re being paid into a 529 account and when they got to the point of going to college, they’d be able to access the 529 account. 

While that initial idea did not pan out, it did ultimately lead to what what Rightfoot is currently doing which is the, you know, the APIs, debt repayment applications and really is just a fascinating view about how founders think differently and how they look and deal with problems. I must say, Dani might be arguably the most resourceful founder I’ve met, thus far, and as you go through the episode, you’ll hear a story about a vacation and her time spent in a van in that vacation. Dani and I also talked about the core problems associated with debt repayment, the impact that debt has on households, in particular, households of those underrepresented groups, whether it be women, minorities, it impacts them significantly more than it does other households, her time in Southeast Asia, raising capital and much, much more

Before you get to the episode with Dani, come on as a guest or sponsor one of our many digital or in-person offerings. Feel free to reach out anytime at todd@fintechnexus.com

Now, without further ado, here’s the episode with Dani Pensack, Co-Founder & CEO of Rightfoot. I hope you enjoy our conversation.


Welcome to the podcast, Danielle, how are you?

Danielle Pensack: Hi, I’m doing great, how are you.

Todd: I’m doing well, thanks for giving us a few minutes of your time. You know, I’d like to kick off, tell the audience, tell me a little bit about yourself and kind of been what’s been your journey, you know, before helping to co-found your current venture which is Rightfoot.

Danielle: Yeah. So, I’m Dani Pensack, I am a Co-Founder & CEO of Rightfoot. Before Rightfoot, I was actually based in Southeast Asia for four years so I worked at IBM out there in tech consulting and I moved out there after undergrad so had an awesome time. I was based in Singapore, but then my projects were in the Philippines and Thailand as well and I learned a lot about APIs which is very relevant to the that business that I’m running today. And then I went to Stanford’s MBA Program where i met my Co-Founder.

Todd: And so, I always like to ask the question, there’s basically two ways or, at least, that I’ve discovered, thus far, of why people start companies. Either they’ve been on that path and have kind of been entrepreneurial by nature or throughout their schooling or throughout their career they found well, there’s a problem I keep on running into, but nobody’s solved it to date and, you know, I think it’s about time that I give that a try. So, kind of where do you fall on that, is it you’ve kind of always had that bug or did you notice some things throughout the time in Southeast Asia or other steps that you might have been, you know, kind of see this issue pop up.

Danielle: Yeah. That’s a great question and I definitely say a little bit of both in terms of my background. So, my Dad had always started his own companies so at a young age I was always kind of helping out, you know, with his business out of the garage and doing everything from like mailing letters or doing invoicing and accounting for the company when I was in middle school and high school. 

My Mom also started her own business too so I’d say I’ve definitely been around that type of environment of being a self-starter, but I’d also say you have to be a little bit probably psycho to start a company (Todd laughs), have a lot of confidence and then be like crazy just going for it. When you think about it, it’s not, you know, rational, to say the least, let’s go do this. I could be making a lot more money if I was just working at a bigger company, but you have some sort of drive, you have the energy, you see a problem that you’re excited about and you just kind of go for it and don’t look back.

Todd: So, ultimately, where did the idea for Rightfoot come from and, you know, when answering that, how’d you come to the name Rightfoot?

Danielle: Good question. So, when we were at Stanford…so I met my Co-Founder, Deirdre, there and we were originally focusing on the problem of how we can help enroll more people into college, specifically lower and middle income folks, and we had this really wacky idea about thinking that, you know, all of these high schoolers have a lot of skills that they’re good at, namely, they’re really great at tech. They could, you know, teach someone something about a computer or developing some sort of program or helping someone write on Facebook, for example, specifically senior citizens was, you know, in our mind a connection that would really be a great exchange there. And we thought that we could help these high schoolers earn a lot of money if they could teach these skills to senior citizens. 

And then the idea was that we would put all that money into a 529 college savings account for these kids and that they would be far more likely to enroll in school. And so, the summer between our MBA one and two years, we actually lived in a retirement home to test out this idea and it was absolutely wild. We had made a list of every single retirement home in the Bay Area, I called probably 150 different retirement homes and I said, hey, I don’t have, you know, money for rent this summer, I’m looking around these types of tests, in exchange I can help out, however, you know, I can run different sections or things like that. And, I would say, you know, a 149 said no and some of them even said, this is illegal, you’re not 60 years old or greater, you’re not allowed to live in this retirement home.

Todd: Oh, really?

Danielle: Yeah I’ve been told that that was a rule, yeah, but apparently something exists along those lines. But, anyway, kept going, right, because you’ve got that spirit of, you know, nothing is going to bring me down, let’s keep figuring it out and one of them said, yes. And he said, you know, we’ve got this extra room, you’ll have to move out a few of the days because that’s when actually seniors will come and they’ll test it out and want to live at the home. But, aside from that, you guys can live there, we’ve got one clean bed, you can share it and you can have free food if you don’t eat with each other, you have to eat with different senior citizens every meal. 

And so, we were like right on, we’re moving in so we showed up and all of our classmates were, you know, like on Wall Street doing investment banking and we were, you know, eating these meals with seniors. At 5:00 pm, we were having dinner and we’re hearing these crazy stories and just engaging with folks and we were dealing black jack and we were, you know, teaching all of these different impromptu sections that we had made up as well as just having an absolute blast. But long story short, we ended up really testing that idea and getting in and running these pilots and what we found was there was this really magical exchange. At the end of the day for the students, they were going to have so much student debt that it just didn’t matter how much they could have earned on our platform, it was just insurmountable. 

And so, we really pivoted around the student, that piece, and my Co-Founder, Will, he’s our Technical Co-Founder who was previously at Google and Deirdre and myself all had a ton of student debt, put it together, we all had more than $200,000 worth of student loans and so it just made sense for us and really focus on what was the pain as opposed to the vitamin that we could be solving.

Todd: So, in terms of the actual product, tell us a little bit more about that, who’s ultimately the target and, you know, tell us a little bit more about the specific product that you guys are building.

Danielle: So, at Rightfoot, we build smarter pipes for debt and so what that means is we are streamlining all of the debt management and repayment functionality and that’s fully embeddable technology so through APIs that different developers can just embed this technology as a feature of their applications. So, we sell into companies, for example, we sell into……we have a top three brokerage firm who’s our client, they’ve got more than 80 million customer accounts, we sell into fintechs and financial institutions so banks as well as neobanks, we sell into benefits firms who want to offer this tax-free student debt repayment benefit entirely under their brand, retirement firms. 

So, I don’t know if you’ve seen the new legislation around the Secure 2.0 Act that just passed December 29th and it now enables a borrower to make a payment to their student loan and their employer makes a match into retirement. So, all of a sudden, while they pay off their student debt, they can get these, you know, earnings in their retirement fund which is really awesome. And so, those are the types of companies who leverage Rightfoot so what we’re enabling them to do is have this smart debt management and repayment functionality all within that single application view and the reason why that’s important. 

So, we’d like to think about it as, you know, Todd, if you wanted to get tacos in 20 minutes, you could just DoorDash it and you get your tacos like now. But think about your debt, right, so people have multiple different lenders who they work with, even you have student loans you could have loans that are private loans, you can have public loans from multiple different providers, you have credit card debt, you have auto loans, you have a mortgage potentially if you’re lucky enough for that and you have to go to ten different websites to see all of them. There’s no way to actually see in one place to understand, my interest rates are different, here’s where I should be paying when, what does it even look like and so…….

Todd: You just described what I do basically every month.

Danielle: Yeah, right. It’s a pain and actually, especially if you look at folks who are living paycheck to paycheck, they’re not on auto pay with their debt because they’re scared they’re going to overdraft with their bank. So, what we see in these interviews is folks are actually making calendar invites to themselves and saying, oh, go ahead and make that payment, don’t forget and, of course, what happens is life happens, it gets in the way, you miss your payment, your credit score goes down and all of a sudden, you’re in a bad position. So, having peace of mind, being able to see and make smart decisions, we’re providing the plumbing and we’re not a standalone application, but rather so that you can access this infrastructure within any application that you know and love and use today.

Todd: You know, obviously debt is a personal story to you, obviously, it is to me and many others, how much of the issue related to debt and even some of the thinking behind the API that you’ve built here goes to kind of this misunderstanding of debt? Are people really fully grasping what they take out, whether it be a student loan or another product and how complicated that might be?

Danielle: Yeah. So, education is definitely lacking in the space. We have a lot of folks who we’ve interviewed who have called themselves “young and dumb” when they took out their debt so that’s sort of a prototype for a kind of a group of folks we have at Persona that we refer to. This is the group who said, when I was younger I made these decisions, I didn’t know what I was doing and here’s what happened and when we look at people today, the types of, you know, payments that they’re making to their debt, it’s really not maximizing their ROI. 

So, a lot of people who say, Oh, I’m on auto pay today, we do a lot of interviews to just be in touch with that customer and people tell us, yeah, I’m on auto pay and  dig further and we realized that they’re actually not on the full auto pay, they’re auto paying for the minimum on their credit card, for example. And, of course, you don’t want to pay the minimum on your credit card if you can avoid it. And so, thinking about things like that, how do you educate someone and say, actually, $20 going here would be far more impactful and have a far greater ROI than if you sent $20 here and so institutions are looking for how do we combine everything under one roof. 

You know, some of our customers, if they’re doing investing, they might want to say, well, how do we kind of pull in the full picture and say, invest this much here, but, you know, if you have this type of interest rate make this payment here, make that payment here. This is holistically how to maximize your wealth as an individual.

Todd: You know, how much of this burden impacts households? I know that when doing research for this episode, you mentioned on your website how much of an impact it hits into either disadvantaged or minority communities significantly more than it does either wealthier or communities that are doing a bit better. How big is that difference between those communities and how much of a burden is that on households, especially those that are kind of living closer to the line.

Danielle: Yeah. So, what I can share are some statistics around that. So, nearly 9 and 10 black students take out federal student loans to pay for college and you can compare this with 7 and 10 white students so really high numbers on both sides. But, ultimately, when you think about you’re taking out student debt, that means that you can’t invest, you’re slower to save for retirement, do all these things that are wealth building so it really does have really big kind of wave impacts going down the line. Some other statistics, so black students are far more likely to be saddled with a larger amount of student debt so 59.5% of black students will borrow more than $29,500, that’s a lot of money. 

When you also think about defaults, so black borrowers are more than twice as likely as white borrowers to default on their student loans. And in a lot of our research what we are also seeing is the people who needed the most help were those who did not actually graduate from college so they were saddled with this student debt, but then they didn’t have the degree to show for it to be able to have a higher earning bucket. And so, all of these messy student loan cancellations that we have going on right now, of course, there’s a lot of back and forth about student loan cancellation. 

Overall, we’re extremely supportive of that legislation and being able to give borrowers the help that they need and even if Biden were to go ahead and wipe out even more than he said he would, this is still going to be a massive problem and it’s growing at such a fast pace. And when you combine student debt, credit card debt and auto loans and mortgages and all of these other kind of type of debt that’s really holding folks back, it’s really impactful to think about how you can help bring customers the solutions that they need right at their fingertips.

Todd: One bit of clarification before we move to the next question. So, say if I’m using a fintech app and they’re not a client of yours, you guys would have to be…they would have to contract you as a client before offering it through their app, correct?

Danielle: Yeah. So, maybe it would be helpful if they shared a little bit of background about like how it works at a high level or why does it rightfully exist. So, if you look at all the lenders and loan servicers across the US, their back ends were built in the 1970’s on COBOL which means that they don’t have just APIs that developers can simply plug into, it’s quite a mess and it really hasn’t been updated. And so, what Rightfoot’s done is we’ve built this modern infrastructure layer that enables us to interact directly with these lenders so we’re sending them funds into their treasury teams or giving them instructions about how to actually apply those funds. 

So, hey, for example, we sent $100,000 to your Master Treasury Department, but because loans are not routable accounts like a bank account, there’s no accounting routing number, that’s really hard ordinarily for a lender to even understand, what do I do with that. So, hey, you just sent me all these funds, what do you want me to do, how do I even apply that? And so what we’re giving them is instructions saying hey, we just sent you $100,000, take $34.18 and apply it to Todd alone and here’s his account information, here’s his sub-account, here’s his guarantor. You know, here are all these very specific things that you need to know, lender, in order to apply those funds to his account and taking off $34.18 and apply to this person and then Rightfoot’s during reconciliation with that provider and then basically feeding that up in the form of modern APIs to the companies that we work with so they can digest and understand what’s the payment status on this loan, for example.

And so, the way that companies were doing that before is they are mailing checks to the lender and, of course, the lenders are like, I don’t know if you remember going into a lending organization specifically like in the student loan world, you walk in and there’s just piles and piles of mailed checks, right. They have massive teams who are just going through these and that’s a pain for them and so count me in in being able to say, let’s fix that for you and also let’s make that a better experience so that people can overall be helped and have a better grasp on their debt to be able to make seamless payments to their debt, etc. 

So, we’re essentially replacing check mailing, of course, there’s really all-bill pay systems that some companies were using before as well, but they are a black box to developers. They don’t have that close feedback loop and they don’t have direct integrations into that lender. And so, we provide an additional layer of transparency that really help the companies that we work with understand the status of payments to debt.

Todd: Picking up on a couple of more technical pieces, how long does it take to say integrate with a lender because if they are using old technology, you are bringing new technology, kind of what does that match look like?

Danielle: Yeah. So, we try to make it as easy as possible for the lender themselves so you could think of us as providing the APIs or building it on their site so that they can receive deep data and the payments without actually doing any extra work. But, of course, working with these providers who were built in the 1970’s does take a lot of time and forging those relationships as well. So, I’d say their first integration end-to-end will probably take about eight months and so when you’re speaking about how there are thousands of lenders and loan servicers across the US, it’s really a big moat to be able to have these relationships and to forge these types of integrations.

Todd: Going back to kind of the other aspect of the conversation, you know, the financial inclusion and financial health portion, how much of a difference can it be to a borrower and just to an individual generally if they were to use something like you guys are providing versus the either spreadsheet or calendar invites or whatever that ultimately probably don’t account for you should be paying more than the minimum. You’re doing this and they’re setting up all these things versus what you guys provide, like how much of a difference can that be for them?

Danielle: Yeah. And even the folks who are doing the spreadsheets are in, I would call them like the healthiest state possible and that’s such a small group, it’s like 2% of people are the spreadsheet type group, the one who’s like really on top of their debt. Most of the people who we spoke with say, I think about it all the time, I wake up in bed, I check all of my different websites, I’m trying to keep track of it, but it’s just like really hard for me to do so I’m trying to just forget about it. And so, ultimately, what we’re not trying to do is necessarily go into like educating a borrower and saying, here are the things that you should do for yourself, but really guiding people on their journey and there’s so much flexibility when you have APIs to be able to come in and say, what do you want that experience to look like. 

And a lot of the partners we work with, some banks and financial institutions will have a lot of relevant data on each person so they’ll be able to really tailor that experience and make it personalized for each person. So, ultimately, when you think about the power of being able to help them with their debt, you know, more than 80% of households in the US have consumer debt. So, when you don’t think about debt an you’re just trying to say, oh yeah, you should invest here, you should save for retirement this much, you have no idea if that’s right or not. And so, being able to really compliment their stack and come in and say, here for the first time is a full view of assets and liabilities together as they should be then you’re able to start working and then start benefitting the borrower holistically.

Todd: When hearing you describe it and talk about it, generally, how much has the shift in the other fintech market overall towards an embedded type technology help kind of set the groundwork for what you guys are ultimately providing. I mean, if this was 10 or 15 years ago, I don’t know if this would be possible just yet.

Danielle: Totally, totally, yeah. It’s all about timing, right, so you’re spot on. There are a number of different companies, I’d even say like larger banks who were in beginning relationship stages who say, hey, you know, our team would have never spoken with you even a year ago, right, like we’re all focused on building everything in-house, everything under our own brand, like we don’t want anyone else helping out. But this idea of them starting to realize and come to the realization that hey, I’m going to, you know, instead of it taking you six months to launch something, it would have taken me four and a half years and it’s that I could use Rightfoot to get to market fast. 

All of a sudden, the messaging is changing and it’s really about sweet market, I’m not saying every company is open to those types of partnerships or relationships, but 100% we’re seeing that change, even, you know, since we started our company, I would say, more and more towards that embeddable adoption. How can I leverage different fintech partners, how am I not viewing them as a foe, but actually a friend who will help me get to market with a better comprehensive product in a shorter amount of time.

Todd: What’s the, if not the biggest and one of the biggest lessons that you’ve learned since starting Rightfoot?

Danielle: I think focus is always the number one, you know, lesson to come away with. I think, specifically for us, when we started out we said, you know, everyone has debts, here are all the different ways that we can help people. And specifically looking at clients, you know, our first four customers were across four different verticals, it’s like lenders, retirement firms, benefit firms, fintechs, financial institutions, these massive brokerage firms and these smaller other startups. And so, when you think about, you know, lessons or takeaways if I was doing this again from scratch would it look like, I would just focus on one of those groups. 

I would look at who’s the fastest growing sector, what are the possibilities there and then really narrow-in on nailing that versus going much wider because the problem is that even though, you know, they’re all using our technology in the same way and the APIs are the same, you can’t cater to them in a very specific way of you’re not only focusing on that. And so, as we kind of approach Rightfoot to a point of that’s what we’re gearing up to, it’s very specific solutions in each of the different spaces so that we can deliver the best possible solution and make no excuses about that.

Todd: Do you have a biggest regret or a regret that you could share.

Danielle: So, I guess the biggest regret was not having that focus at the beginning. I think, you know, for us that just meant that we really spread our attention and we had to hire different types of roles earlier on. I don’t know if you’ve heard of the…it’s a two-pizza role, just like if you have a team where you order two pizzas and everyone, you know, you can feed the entire team with just those two pizzas, like that’s great because you’re able to move really quickly. 

So, I think when you expand the team really early on even if you’re getting that traction, if you’re not specifically focused on one protocol or one type of customer it really hurts the team because then they’re growing at a faster pace and you’re trying to figure out, how do we all work together, how do you communicate differently. I think, especially in this remote world. So, our team is spread across the US, it requires a lot more documentation, a lot more intentional communication to make sure that everyone’s on the same page. So, another regret is not setting up that documentation and infrastructure to be able to have a remote first work force.

Todd: You mentioned before the experience you had by going into the retirement home versus maybe some people that were on Wall Street, I mean, how much, you know, of that experience shapes kind of how you’re shaping ultimately Rightfoot and do you think it could have been different had you gone that more traditional route of Wall Street or maybe interning at a big bank, like how much does that experience really shape what you guys are building?

Danielle: So, I think it shapes or building a lot because it all comes down to willingness to pivot and not being in love so much with an idea that you can’t see around the corner and understand that you could change a little bit to make it far more impactful. So, our legal name is Charitized, Inc. and it’s actually a tribute to our original concept or idea of how we started and launched and our lawyers kept telling us, why aren’t you just changing it legally to Rightfoot, it’s so easy, and we’re like, listen. this is a part of our DNA, we’re fast pivoters, we learn quickly. 

And so, I think you know, to your question, I worked at big companies before like IBM and I had tremendous experience there, but thinking about all of the quick learnings that you can have in launching your own company, there’s just nothing to compare to that and really figuring out, how do you learn fast, how do you fail fast, how do you make sure that you’re not blinded in any way and you’re looking around corners and asking the right questions.

Todd: You know, one thing that comes to mind, when you hire new people, do you tell them that story and kind of the legal name is this. I mean, I’m sure it gives a different color to a company versus just hey, we’re Rightfoot and this is what we do. That experience kind of gives you character versus say the maybe more traditional route.

Danielle: Definitely. So, we’re at 19 people now so it’s a nice, intimate group so you know, the people who come onboard are aware of our founding story, how we got started. You know, they’re all mission-driven and excited about maximizing welfare and underrepresented Americans, specifically, first starting out with tackling folks’ debt. So, you’re so right, I think it’s the kind of people who are attracted to a company like this, the ones who really want to go early stage, maybe they’ve been there before and they’re energized by it, maybe they took a break and then came back for more. But those are the kinds of people that you want to build a company with, who are just so excited about those future pivots and what’s in store around the corner.

Todd: You know, obviously all companies need capital. When going to investors and talking to investors, how was investment appetite and how do you think of choosing and looking at investment partners. Is it just a check, are you looking for a long term partner in a relationship, kind of how do you think of that investment relationship with VCs and other potential investors?

Danielle: So, for us, it’s definitely about that relationship, it’s about who are the people that we’re going to work with, that we can show up authentically saying that’s also really a big piece for us. So, having two female founders, you know, understanding that fewer than 2% of funding goes to women, like that’s something that’s so insane to think about. But it means that, you know, the way that you show up could look differently and we really wanted to make sure that the partners that we choose are, you know, behind us in our decisions, are aligned to our strategic viewpoints, that we can work with them, that they’ll push us to be better and those are the types of investors that we chose to partner with. We’re really excited about that. 

I’d also say, when we were raising our seed round previously, we had a really kind of great approach of finding these awesome angels in our space who are relevant to what we were doing. And so, we would kind of have this approach where we would have a list of people who are our targets and we would go after them and we would explain what Rightfoot does and really try to get them onboard. And when they would come onboard, we go to another angel who we really admired and respected and then say hey, there are other angels onboard, are you interested in joining this type of community. And we did an investor kick-off for everyone so they felt like they could all meet each other and so we had everyone from like, you know, former COO of Venmo to one of the founders of Plaid to the COO of Marqeta so all of these really great folks who we’re able to bring onboard and have as a part of our team.

 Actually, it right before Christmas break, I had sent out an inventor update and I included a link for introductions that I’m looking to get and everyone was just so  active in it and some of our investors were offering 12 different connections which is just crazy, you know, that level of activity and you’re able to really leverage their connections because they want you to be successful ultimately. So, being able to say okay, great, it’s not just I’m updating them, but it’s how can we actually help each other and how can they help make my company successful.

Todd: I mean, you mentioned it when we started talking about, you know, the investment piece fewer than 2% of startups run by women are funded. You know, when going into the investment process, how A) is that daunting to look at that and say, wow, we have a higher bar to reach and then B) when you start getting those kind of how do you react to that and counter that because you talked a little bit about the process you have, but beginning the process did you have reticence, did you rethink or kind of what was the mindset going in knowing some of those daunting statistics?

Danielle: Yeah. So, great question and for anyone who’s listening, if you are a female founder, if you are an under represented founder, if you want to reach out to me and get tips, have me review decks, things like that, I’m happy to help out, but at a high level, 100%. So, you do have to approach it differently, you are graded with different criteria, whether or not folks are sort of understanding that that’s what they’re doing so the types of questions you will be asked will definitely be more around like show me proof points as opposed to tell me the story. 

And, I think, especially as we’re gearing up for or already are in a much tighter funding environment that means that even more scrutiny is going to be on women and underrepresented founders. And so, thinking about the ways that you could psych yourself up for success so that means really leveraging your network, getting introductions or back channels from founders of that portfolio company that you’re trying to get in front of.

So, never reaching out to an investor directly and saying hey, you want to take my pitch meeting, but really saying okay, great, how can I drum up the support, how can I be really succinct with my facts so growing at this rate here’s how much we have booked, here’s what they would look like in the future so really going for that future approach so our sales will cross X by the end of 2023, etc. So, those are just kind of a few things, but really it does take a lot of time so making sure that you give yourself that space and are gentle with yourself because, I think, oftentimes founders, you know, you get really caught up in the fact that you might view yourself, like your own identity is the same as your company. 

So, if I’m getting a no in fundraising, that means they are telling me, Dani, no, kind of like Dani and so I think that’s something that’s really important for founders to be able to, you know, talk with the therapist about which is something that I recently…. you know, I recently started doing therapy. I love it, it’s so helpful, but fundraising is really difficult in this environment. And so, being able to, you know, find the right support system is really important, but also know that there is money out there for great companies and you will be successful if you’re hitting the right metrics that you psych yourself up for so definitely happy to talk more with folks about that.

Todd: We have just a few minutes left so I’d like to end the episode a bit lighter than we started. Do you have a favorite book or the last book that you read.

Danielle: So, I just finished a book called “The Messenger,” that was a really interesting book, I’d love to chinkle, also “Circe” if you’ve ever read that one, I really like that. I think some of us like fun, light books are great, I’m also really into comedy, I think especially as a founder, but, you know, there’s a side of you that wants to just like take on something super light. So, TV shows that are fun and uplifting are always great.

Todd: You know, you’ve mentioned focus through the episode, you obviously just mentioned kind of watching or listening or doing something lighter, I mean, what else do you do to unwind? Obviously, founders work hard, sometimes they probably overdo it, but ultimately, you can’t run the company unless you are clearheaded and focused and energized, is there anything else you do to unwind and kind of step back a bit?

Danielle: So, last year I actually started an adult kickball game or like basically formed a team and had a bunch of friends pool together for that. And so, you know, when we’re like 30 year-olds who are just like playing kickball, it’s just this wild, hilarious adventure and so we would go every Wednesday to this field and we play against other teams and it was just a blast. You cannot forget what it means to feel like you’re on a sports team and you’re high fiving each other and you’re cheering for each other. 

And then it’s the same kind of environment that we try to create in the office, but it’s really hard to do remotely, like you can’t just high five someone so I’m feeling people crave that kind of energy so that was awesome. We’ll definitely be doing that again this year and running, getting out all of the, you know, energy, getting the endorphins going up. Those are some of the things that I really like, I think like being on a actual sports team and having people to high five is something that’s really motivating and something that I know I’ve been craving before.

Todd: Speaking of sports, do you have a favorite team or favorite sport that you watch other than kickball?

Danielle: Oh, I‘m from Boston so I think I have to say Red Sox, always threw up with everybody, just loving the Red Sox. And, you know, I live in San Francisco now so the Warriors, they’re obviously great as well, I love to go to Warrior games whenever I could. What about you?

Todd: Well, obviously, you see that I’m wearing a certain sweatshirt here, the Buffalo Bil, who are playing this weekend in the playoffs and being from New York, I’m a big Mets fan and college football as well which is Notre Dame so.

Danielle: Nice, yeah, (cross talking) so I went to Tulane for undergrad.

Todd: That was a surprise and quite a win, especially over USC who Norte Dame fans hate so that was nice to see. (both laugh)

Danielle: Yeah, so that was great, I’m glad we could be helpful.

Todd: Do you have a favorite vacation spot?

Danielle: So, more recently, it was actually over Christmas break, I decided I really wanted to unplug so my boyfriend and I went to Maui so we got some really cheap flights on Southwest about a year in advance and then what we realized us there were not Airbnb’s and no hotels that were, you know, cheap and obviously at a founder budget I was like, what do I here, do we have to cancel the trip and then started researching. We found out that you could rent a van and you could actually sleep in a van and so we ended up renting a van for six nights and going around Maui and we just, you know, had a mattress in the van and we would open back the back doors and kind of pull into the beach so you could just hear the water behind you and it was absolutely magical. 

I’d say, just like from living in Southeast Asia for four years, you know, going to Sri Lanka and going to Bali and going to Indonesia, other parts of Indonesia, Mount Bromo was a wonderful trip where we were going up to craters, absolutely, I mean, I love Vietnam and Thailand. I’ll never stop traveling whenever I can, I absolutely love it.

Todd: Yeah. It’s funny, not many types of people would figure that out in terms of the van. I think founders, though, are different, are made from a different cloth because hearing you talk about it, even the story before about, you know, the founding story with the retirement home and everything. I mean, founders that I’ve talked to, they just think differently, they tend to not do alright, I’ll watch football every weekend or something like that. I had one founder who said he plays underwater hockey which I didn’t know existed. (Danielle laughs) So, there’s just this different mindset which I find fascinating when talking to founders.

We have one final question which is, you know, what do you find inspiring, what inspires you?

Danielle: People (laughs). I find people inspiring, I find traveling inspiring. So, when I lived in Southeast Asia for four years, I got to go to so many different countries and you’ll see so many different ways of life, like it’s really hard to not feel like you’re stuck inside a bubble, especially like as a founder in Silicon Valley, you cannot forget what the world is like. And so, I think the way personally to do that is by traveling, but in super scrappy ways like what I was talking about like doing a home stay, for example. 

So, I did that in Laos, I stayed on a farm with goats and so these kinds of things where you just really get to know people and get outside of the zone and people let their guard down and are talking to you about everyday life and you’re thinking like wow, our lives are so different, but they’re actually pretty similar. Here’s the way that we’re similar and ultimately, you know, the world is big, but it’s also very small at the same time. So, I think remembering that and staying down to earth, those are the things that I find inspiring.

Todd: Well, Dani, I appreciate your giving me a few minutes and coming on the show, If someone wanted to reach out, either about some of the founders tips that we were talking about before or wanted to get in touch with Rightfoot, how would they do that, how can they reach out?

Danielle: Yeah. So, you can go ahead and friend me on LinkedIn, it’s just Danielle Pensack or feel free to drop me a note at danielle@rightfoot.com

Todd: Thank you very much, continued success to you and the team and hopefully, we’ll get you back sometime in the future.

Danielle: Thanks, Todd, appreciate that.

Todd: Thank you.

  • Todd Anderson

    Todd is the host of PitchIt: the fintech startups podcast, a weekly interview show featuring emerging fintech founders and leading venture capitalists. He is responsible for leading the content team which covers fintech through daily & weekly email newsletters, editorial, virtual events, and in-person conferences. He has been covering fintech, banking, and venture capital for more than 15 years, including speaking regularly at industry events.