The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/HR/slice podcast
slice podcast artwork

somrat niyogi / recall capital

slice podcast · 2026-03-17 · 37 min

0:00--:--

Key moments - from our scoring

Substance score

66 / 100

Five dimensions, 20 points each

Insight Density13 / 20
Originality11 / 20
Guest Caliber16 / 20
Specificity & Evidence12 / 20
Conversational Craft14 / 20

Somrat Niyogi's journey reveals how operator experience shapes a fundamentally different venture approach. After founding Miso (acquired by Digit in 2013) and Stitch (sold to Sugar CRM), then operating at Clary and Gusto, he started angel investing with the philosophy that value comes from leveraging relationship capital rather than just deploying checks. Recall Capital, launched in 2023, scales this operator-centric model with $14M in committed capital (building $25M Fund II) focused on $300-500K pre-seed checks into AI-native B2B companies. Rather than just being a capital provider, Niyogi positions Recall as a go-to-market partner - helping founders build pipeline, close deals, run events, and navigate the sales engagement category he knows intimately from his time at Salesforce and as a founder. This fills a gap he observed: even experienced founders starting B2B companies struggle without active sales coaching and network activation. His fund operates with collaborative ownership models, avoiding the dilutive early-stage ownership expectations of larger funds while maintaining 10x return potential relative to fund size.

Key takeaways

  • →Recall Capital differentiates by providing hands-on go-to-market coaching and pipeline-building support rather than passive capital, filling a void most VCs don't address at the pre-seed stage.
  • →Somrat's angel investing success came from lending relationship capital and social capital to help founders get traction before they had anything, becoming the most active non-institutional investor on cap tables.
  • →The founder thesis behind Recall is that AI-native B2B companies need a partner who understands sales engagement, revenue generation, and founder support through multiple pivots and stages - not just institutional branding.
  • →Even at Recall's smaller check size ($300-500K), targeting 3-5% ownership relative to the fund size allows for 10x return potential while staying collaborative rather than ownership-focused.
  • →Somrat's operator background across Salesforce, multiple founder exits, and roles at Clary and Gusto gave him credibility and pattern recognition that pure VCs with no sales or go-to-market experience lack.

In this episode

  1. 1Early career at Salesforce and transition to startups
  2. 2Founding Miso in social TV and the ecosystem around Salesforce
  3. 3Building and exiting Stitch as a mobile email company
  4. 4Operating roles at Clary and Gusto to learn enterprise dynamics
  5. 5Angel investing and the philosophy of value creation over capital
  6. 6Starting Recall Capital to support B2B AI founders from inception

Mentioned

Recall CapitalSalesforceSiebel SystemsRight 90MisoStitchClaryGustoGoogle VenturesServiceMaxCaptivate IQSomrat Niyogi

Guests

Somrat Niyogi

Topics in this episode

SalesforceGustoClaryRecall CapitalAI-native B2B companiesGo-to-market coachingSales engagement categoryMisoStitchServiceMax

Questions this episode answers

What is Recall Capital's investment thesis and check size?

Recall Capital is a $14M pre-seed fund (building a $25M Fund II) that writes $300-500K checks into AI-native B2B companies. The fund operates collaboratively, targeting 3-5% ownership relative to fund size rather than high absolute ownership, with the core thesis that founders need active go-to-market partnership and revenue support from inception.

How does Somrat differentiate Recall from other venture funds?

Unlike most VCs, Recall provides hands-on go-to-market coaching, pipeline-building support, sales coaching, event facilitation with founders and buyers, and active customer sourcing - leveraging Somrat's decades of sales and operator experience rather than just deploying capital passively.

What companies did Somrat found before starting Recall Capital?

Somrat founded Miso (social TV startup acquired by Digit in 2013) and Stitch (a mobile email company for salespeople, sold to Sugar CRM), both of which taught him lessons about founder challenges, market fit, and the importance of go-to-market execution.

What was Somrat's first successful angel investment and what did it teach him?

His first was an advisory relationship (not capital) with Maxplor Technologies in 2009, which rebranded as ServiceMax and sold to GE for $900 million. This showed him that value comes from relationship capital and time, not just money, a principle he carried into all his angel and venture investing.

Why did Somrat leave operating roles to start a venture fund?

After running an angel fund while at Gusto, he saw a market need for a strategic go-to-market partner for B2B founders at inception, especially as AI companies all started looking the same. He wanted to write larger checks and build portfolio construction while scaling the support model that had worked in angel investing, rather than continuing to operate or join an existing fund.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

13 / 20

The episode contains solid operational insights about B2B founder support, sales coaching methodologies, and fund construction, but is heavily padded with career narrative and biographical detail that reduces insight density. The valuable substance - how Somrat operationalizes founder support through monthly engagement, event programming, and sales coaching - is interspersed with lengthy storytelling about Salesforce, Miso, and Stitch that, while interesting, doesn't directly teach B2B operators new operational lessons.

What we try to do is consistently show up and create value in a revenue oriented mindset every single month until they get to the next round. That sometimes is directly in the context of, let me go build pipeline. Some of that is also saying, hey, you have pipeline, let me help you close it.
I actually do sales coaching as though they're hiring a professional sales coach. Maybe that's not the need in month one. Maybe month two is now I'm stuck in stuff. Maybe three, I got pipeline and now I got to close it.

Originality

11 / 20

The core thesis - that emerging VCs should provide hands-on sales support and founder coaching beyond capital and intros - is increasingly common in early-stage VC positioning. The 'help founders get revenue traction' angle and event-programming approach are somewhat original to Somrat's execution but not conceptually fresh. The investment thesis around AI disrupting legacy SaaS stacks is well-worn territory by 2024.

There is going to be a complete disruption of cloud legacy SaaS. What do we think of the top companies, whether public or private equity owned, we think that in five years it's going to be a completely different stack.
I don't think there's some aspects that's probably a bubble, but there's also some real fundamental opportunities we're seeing that are really impressive at the business fundamental level.

Guest Caliber

16 / 20

Somrat Niyogi is a strong guest with legitimate operating credentials - two exits (Miso, Stitch), roles at Salesforce, Clary, and Gusto, plus active angel investing experience before launching Recall Capital. He's a true practitioner rather than a career podcaster or pure theorist, and his dual founder + operator + investor background is genuinely relevant for B2B audiences. However, he's an emerging manager with a small fund ($14M F1, $25M F2), not a marquee figure with massive exits or category-defining wins.

His whole career has been in the Valley as an operator, founder, and now investor in venture capital, early stage ecosystem.
I was very fortunate the way that Andy and the leadership ran their board meetings. I sat through every board meeting. How does Sequoia and Bain Capital and other investors operate in the room?

Specificity & Evidence

12 / 20

The episode has moderate specificity. Somrat provides named companies (Salesforce, Miso, Stitch, Clary, Gusto, Recall, Captivate IQ, ServiceMax) and specific fund sizes ($14M F1, $25M F2, $3M Stitch raise, $900M ServiceMax exit). However, on operational details, specificity drops: fund check sizes are ranges ('3 to 500K', 'average 400-500', '600 to 900'), portfolio construction lacks numbers ('30 to 35 investments'), and the sales coaching methodology is described in general terms rather than specific frameworks, metrics, or examples.

ServiceMax and they ended up selling to GE for $900 million.
For fun too, we are going to write larger checks. Our average is around 400, 500 right now. We're going to be writing 600 to 900 and fun two.

Conversational Craft

14 / 20

The hosts ask solid, probing questions about fund structure, investment thesis, and founder support mechanisms. There are genuine follow-ups ('Is that part of your diligence?') and some light pushback ('everyone gives capital and everybody gives intros. That's a pitch that we hear quite often'). However, the hosts rarely challenge Somrat's claims or press him on contradictions (e.g., how monthly sales coaching scales across 30+ portfolio companies, or specifics on 'kingmaking' in AI). Most questions are open-ended invitations for Somrat to tell his story rather than hard interrogation.

Is that part of your diligence? Do you offer customer introductions before you invest?
Everyone gives capital and everybody gives intros. That's a pitch that we hear quite often from different emerging managers. What do you think that you're doing that founders can't get anywhere else?

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

speaker39fund34founders29help28capital22called19salesforce18ended18angel17back16early15sales14building14started14founder13market12

Episode notes

Somrat Niyogi is the Founder and General Partner of Recall Capital , a $14M Fund I now building a $25M Fund II, writing $350-900K checks into AI-native B2B companies. Before Recall, Somrat joined Salesforce as an early employee. He went on to build two venture-backed companies, and spent years as an early operator at Clari and Gusto. His network runs deep because he was there early, at most of the companies that matter in San Francisco. He and his wife Sarah , first general counsel at Plaid, six years at Scale, started angel investing together out of their own network. Recall was the natural next step. Somrat runs buyer dinners for his founders, fills the room himself, and does sales coaching the way a hired coach would. He’ll also tell you he was one of the worst CEOs during his first company. Decades of operating and building, and he still hasn’t found the ceiling. You get the sense that clarity about what didn’t work is what makes him sharp about what Recall is supposed to do and the resilient founders they back. Full episode below, or on Spotify / Apple Podcasts

Full transcript

37 min

Transcribed and scored by The B2B Podcast Index.

speaker-0: What we try to do is consistently show up and create value in a revenue oriented mindset every single month until they get to the next round. That sometimes is directly in the context of, let me go build pipeline. Some of that is also saying, hey, you have pipeline, let me help you close it. Which is a whole different art than most VC funds don't play in.

Most founders have never been classically trained, well, let me help you. I'm stuck in opportunity. actually do sales coaching as though they're hiring a professional sales coach. Maybe that's not the need in month one, maybe month two is now I'm stuck in stuff.

Maybe three, I got pipeline and now I got to close it and then I got to go back again. I do it all over again. It evolves. So it's that consistency of engagement that really matters for a founder and they can count me on it.

speaker-1: Episode four, happy St. Patrick's Day, everyone. Today we're talking to Shamrat of Recall Capital. His whole career has been in the Valley as an operator, founder, and now investor in venture capital, early stage ecosystem.

People know him for his better half and the fund that they've built together and how deeply embedded they are as a true power. capital in the Silicon Valley ecosystem. speaker-2: Yeah, Shumrat does a lot of work to put together really great events between his founders, buyers, and LPs where he then becomes aware of a lot of the signals across the Valley. He's definitely a sales guy through and through always hustling to find the best people to connect his portfolio founders to, whether as a customer or just to bring clarity to his go-to-market support that he likes to do for his founders.

speaker-1: Now without further ado, let's get into it. speaker-2: So Marat, welcome to the Slice pod where we uncover the stories of fresh emerging managers across the early stage venture landscape. You're the founder and general partner of Recall Capital, a $14 million pre-seed now building a $25 million fund too, writing three to 500K checks into AI native B2B companies. You've had this long career in B2B software, founding companies, working at Salesforce, Clary, Gusto, Angel Investing.

Was venture capital always the plan for you or did this kind of just unfold over time? speaker-0: If you have a plan, you're not really experiencing life. Life is a journey of experiences, meeting people and learning more about yourself. And so it would be foolish to say I've had this aspiration of being an investor.

It's been a journey of seeing what it meant to start companies. I've been a family of entrepreneurs and both of my brothers are entrepreneurs. started college in Austin. In 1999, Austin was another growing area of entrepreneurship.

I think that's where I caught the bug and have had the unique fortune of joining great organizations, seeing companies go from the early stage to growth. you know, once you've experienced it, you kind of want to be a part of it and activate it. speaker-2: Let's go back to University of Texas, where you studied computer science. What were you thinking your life would look like?

speaker-0: My parents are of Asian descent. So as always, ⁓ there's only a handful of logical paths, become a doctor, become an engineer and find a stable job. I'm very fortunate that I have an older brother. He's 10 years older than me.

He went to MIT and he's always been on the forefront of innovation and technology. lot of my early interest in startups was through him. My break into. Silicon Valley, this was 2003.

I really wanted to come out here. University of Texas is kind of a recruiting bend for a lot of big companies, but when it came to startups, a lot of the startups in the Bay Area could recruit from Stanford and Berkeley and so forth. 2003 was a really tough time in technology. There was a lot of layoffs.

I actually had a job at a company called Siebel Systems. Siebel was the initial pioneer of CRM. I was supposed to come out here. Ended up just happenstance that I literally met my manager at Siebel on a Sunday.

And then the next day he calls me while I'm looking for an apartment in San Mateo and he says, Hey, I have to let you go. Unfortunately, we're doing a downsizing. had a friend at Austin who was a COO of hire.com.

These are the type of relationships that last decades. He said, Hey, you should go interview for a competitor. So I actually Googled Siebel competitors on page six of Google. was this little upstart called salesforce.

com. I found an email address and I said, Hey, I just got laid off from Siebel. They said, we don't really recruit out of the Bay area because there's a lot of great talent here. And I said, Hey, think of me as a local.

I was like, I'll just price line a flight from Austin to San Francisco. When I joined Salesforce just launched their API. It was called S-Force at that time, the tools to migrate data from one CRM to Salesforce were nonexistent. There was a lot of bugs around the initial version of the API.

They needed someone young to really learn not only Salesforce, but every other CRM system on the planet. If your data is not there, it's really hard to visualize what's possible. I would work the midnight oil and in lot of cases, some of the largest accounts and shown what Salesforce can do. For several years, I became the data person and ended up selling data services and building some of the initial data programs that are continuing to be used today.

I trained. some of the first consultants from Accenture, from TCS at the time. speaker-2: And I think it was around 2006 and maybe a few years after Salesforce, you ended up joining another startup called Write90, sales forecasting startup. Did you see data moving in a certain direction that you wanted to follow?

speaker-0: I was part of the consulting organization in Salesforce. I remember flying to Mobile, Alabama, to Seattle, and someplace in the middle of Iowa. There are certain markets that are fairly large and unique that have unique challenges. This was 2007.

Salesforce launched their ecosystem called the AppExchange. There's a famous story of Mark Benioff selling AppStore to Steve Jobs. I saw this opportunity of the ecosystem building around Salesforce. This is when legacy SaaS companies, Marketo, Was just getting created, which was a fairly large market tech company that Adobe acquired.

There was another company called Viva, which is now public. There was a company called service max, which was centered on field service. I saw the vertical market evolving and there was a company called right 90, which was focused on advanced manufacturing. I wanted to go in super early.

I wanted to be a jack of all trades. They needed someone who could help sell, who could help service, who could be SSE. You're young in your life and this is the best time to learn how to do things. so, ⁓ took the leap of faith, joined right 90.

And that kind of taught me about what it means to be at a really small company and doing whatever it takes to drive revenue. speaker-2: And then you co-founded Miso in social TV. What was the vision back in 2009? speaker-0: At that time, social was huge.

The intersection of enterprise software and social media was converging. When you see a technology shift, it's hard to sit on the sidelines. Having seen the movie at Salesforce, I wanted to be part of the next transitional technology shift with social. A colleague of mine at Write90, he and I were tinkering around building apps on Facebook.

This is before Facebook had Facebook connect and logging on Facebook. The way you would engage with Facebook data is actually through the walled gardens of the Facebook interface. There was this kind of crazy madness of large brands building apps on Facebook and they needed help. One thing led to another.

I ended up building apps on Facebook. joined an ad network through that experience of selling ads, building relationships with ⁓ advertisers. I had this sort of simple naive perspective, which was. Advertising is a lot of relationships driven and I built all these relationships with large advertisers.

If I can build something that could capture someone's attention and people use it, I can go sell CPA based ads. One thing led to another, and I was experimenting with things. One of my friends from college was transitioning. Hey, I'm looking to try something new.

And so we both quit our jobs and started building mobile apps. Twitter was becoming all the craze. We built a first kind of failed idea called FlixUp. Folks wrote about it.

was like a rotten tomato. were analyzing Twitter data and what people were chatting about. This is when Twitter just opened up their social channels. The thesis was if we can mine the data that exists in Twitter around what movies people are chatting about, maybe we can become a competitor to rotten tomatoes.

But not many people are watching movies. So we said, why don't we do this with TV data? Four Square came out and all of sudden people were checking into all these cool places and I was like, Hey, the average American in middle America is watching a lot of TV. What about the people that are not going to the cool kind of bar?

We were bootstrapping this whole idea over a curious of months. There was an office space in San Francisco, Pier 38. This is where Instagram got started. Twilio was in the same space as well.

Mesa was found in that same corridor. We got some press because of Flix Up about our early iterations of what they called the four square for TV. There was someone senior at Google that quite frankly just inbounded me cold and grateful for him. And he said, Hey, do you know what you're doing?

I was like, I don't know what I'm doing. We jumped on the phone and a lot of the inception of Miso, he helped articulate through that process. He was like, Hey, are you thinking about raising money? And I was like, I don't know any investors other than what I know in peer 38.

And he goes, well, why don't I connect you? There's this emerging fund that Google's creating Google Ventures. You should chat with them. This is.

before Google Ventures had a website before it was even announced. As a matter of fact, I actually said no to Google Ventures because I wasn't sure if they were legitimate when they came with an interest to invest and the rest is history. speaker-2: And that got acquired in 2013 by Digit. What was the story there?

speaker-0: Quite frankly, I was not the best. I would probably argue I was one of the worst CEOs out there. You learn a lot about yourself. You learn a lot about what it takes to build a company.

I went through a lot of hardship, a lot of pivots. We went from checking into TV to social experiences that Facebook built their own sort of check into TV. And I was like, now I got to be there. It's Facebook, which is not a good place to be.

Our team was relentless going along with every pivot. And at some time it just kind of wanes on me, not only on me, but more importantly, the team of like, where is this fucking thing going? We had raised money from Hearst. We raised money from Google Ventures.

We had money from COSLA. The truth is nothing took off. We had several million dollars in the bank. And the question was like, do we do a hard pivot?

And decided quite frankly, that the team was just exhausted by the category. Like no one won. The whole category didn't take off. So we decided to sell the assets.

return the capital and go back to the drawing board and figure out what want it to do next. speaker-2: And that next was Stitch, which you started pretty quickly after me. So what's going through your head? know Google Ventures invested again.

What were you hoping to change about the way you were going to build Stitch? speaker-0: At the end of Miso, I was like, I want to work on a problem I really understand. For whatever reason, I was engaged in a consumer market on an ad driven business and I had no place to be in those buckets. I did okay.

But was I the best person to start that company? Absolutely not. I remember having a conversation with my wife. Maybe this is ego.

Maybe this is a chip on the shoulder. It made a combination of all those things, but it was an idea that I had. And I said, Hey, Give me six weeks. think if I can go start something, which basically hire the team that I feel like is going to be great for this problem, let's go raise capital on an idea and let's go make something happen.

Six weeks ended up raising, I think like $3 million from great investors. I've always been traveling for sales related reasons and I can't be productive when I'm on the go. Leaving meetings, I'm missing follow-ups. I'm doing back-to-back meetings.

How can I be more productive? I was thinking about the intersection of email, calendar, CRM, going back to what I knew. This is a product that I could talk to hundreds of salespeople about. ended up starting Stitch, which initially started as a mobile email company geared towards salespeople.

ended up running that for two years. One of our competitors was a company called Relate IQ, who ended up getting acquired by Salesforce and Realized, ⁓ my God, like I'm literally in the Salesforce ecosystem and now Salesforce owns that. me go, you know, sell the company to another CRM player, end up selling it to another player called Sugar CRM. I ran this company way better than I did with Miso.

The way I led, the way I built relationships with our team. The second time founders, they learn a lot from their first time experiences. And I'm friends with every single person in that company today. speaker-2: And after building those two companies, go on to join Clary and Gusto.

Instead of starting another company, what was going through your head at that point? speaker-0: I was pitching as a founder does lots of different VCs. One of the partners at Sequoia, Olly said, Hey, you should take a look at this company called Clary that we seated. Maybe you can be helpful to the founding team.

You know a lot about the category. I was grateful that Andy Byrne and Venkat who are the founders of Clary, Hey, come here and help us out. And there was not the clear job description at the time. My wife was like, If you start another company, I'm going to be super pissed.

And you got to factor all those things into consideration. Ended up joining Clary as it was near zero ARR and played a lot of roles. I was very fortunate the way that Andy and the leadership ran their board meetings. sat through every board meeting.

How does Sequoia and Bain Capital and other investors operate in the room? How do you run a great board meeting? You just don't get to see these things. I ran my own board meetings, but I didn't get to watch someone else.

just did it myself. Now that I reflect back, I probably did a really bad job. And so I just really want to learn from folks that have been there, done that. Leaving Clary was a personal choice.

I really wanted to try something completely different. Sometimes as a challenge to yourself, you're like, Hey, I've done a lot of go-to-market stuff. I started a go-to-market company. I've been part of Clary.

I was at Salesforce. One of my executive friends said, Hey, they're looking for a BD leader at Gusto to help think about. all of the aspects in the build partner buy journey. And I was like, I don't know anything about HR.

And what ended up happening is I ended up chatting with the COO, Lexi Reese, who's actually a founder of a company called Lanai. And I said, I don't really know a about HR, but my favorite thing to do is to learn about markets and ideas and what's possible. And so I went down the deep end and then she's like, okay, great. Well, here's a project for you.

I probably have still the assignment, which was like, What are the various channels of growth that will 10 X our revenue? And I was like, all right, I'm to go do it because I need to learn about this category anyways. And that's when I learned about the massive market of HR and the different types of wedges. By the way, there was no deal.

There was no remote, no rippling. None of these things existed. If there's something I learned at my time at various companies, the market size matters. How do you differentiate yourself in a crowded ecosystem?

I actually. I don't think I was the best hire. There are people from other companies such as Workday, such as ADP that were probably better fits. They gave me a chance and I came into Gusto and knew nothing and left learning a lot about the category and starting doing some angel investing more aggressively at that time at Gusto around the ecosystem.

And that was my last stint and did a lot of things at Gusto, product partnerships, channel. And building our API or ecosystem. And then I ended up building our embedded payroll business, which was the last thing I did. speaker-2: And those angel investments became an angel fund that Bain Capital Inc.

speaker-0: Bain kind of knew me just because I was sitting through all the board meetings and they saw me as an operator, but they also started seeing me on cap tables. RF was like, Hey, have you thought about starting a fund? And by the way, I was like, I don't know you're talking about. I got this job at Gusto, but thankfully for these platforms like Angelist, you can do these things on the side.

So I ended up raising an angel fund, reaching out to some high wealth friends and running this. didn't have that much liquidity personally. so raising a small fund where we can run. 25, 50 K checks invest in 45 companies in problems and domains that I was super excited about and partnering with other venture capital funds as these companies graduated.

That was a 21 vintage. It's still running strong. lot of my passion areas of markets. I, it was kind of built from my time at Gusto, everything from HR to embedded FinTech to areas like vertical SaaS.

I was doing that full time while also running a team and starting a new business line at Gusto. speaker-2: Do you remember your first angel investment? speaker-0: Well, my first investment was in 2009. This was a bit more of an advisory experience.

It turned out to be a successful exit. This is going back to when I joined the emergence of categories around Salesforce ecosystem. There was a startup called Maxplor Technologies and emergence capital, which everyone knows about back in 2008, 2009, there was a gentleman. He just joined from Salesforce there and he goes, Hey, Shamrat, like.

This company is trying to navigate the Salesforce ecosystem. Can you help them out? I joined as an advisor. I didn't invest capital, but I a lot of time.

That company ended up rebranding as ServiceMax and they ended up selling to GE for $900 million. And so I was like, huh, it wasn't about capital. It was about value. And that has always stuck with me.

I didn't have money at the time. I was fairly young, but I can help someone. And if you can help someone, it can also create value. so my foray into investing started as, let me help people.

Let me advise companies. That was my first kind of foray. up getting an exit out of that and helped put a little bit of down payment on the house kind of thing. And in around 2018, 2019, as I started building a point of view, I ended up reaching out cold to a startup called Captivate IQ, which was a sales commission software company.

knew a lot about. sales comp and sales ops because of my time at Clary. And I said, Hey, love to help out. Maybe I can get you some early prospects, some customers.

There has to be a better alternative to the cloud-based exactly player who is at the time, this was 2018, still very early. This is before they got acquired by Vista. And so a lot of my early investing started with time and helping founders. Some of the early customers of Captive at AQ were sourced by me.

And I was like, this actually matters. Like actually helping a founder where you have conviction, you believe, but more importantly, doing something about it. Everyone has a network, but the question is, you do the uncomfortable thing and actually say, Hey, I know this is a startup and who knows whether it'll succeed or fail, but you should take a look at and have a meeting with this person in first place is kind of became the way I love to operate. Let me help people first.

The ethos of when I started an angel fund was when a founder has nothing, especially a B2B company, you have to help them get some traction. You cannot sit on the sidelines. If you take your relationship capital and your social capital and break through, what can you do for them? It's risky.

Most people don't want to do it because it could backfire. And yeah, sometimes it does, but I have been on that side and I'm just not going to be that person. If I believe in something, let me go help it. A lot of my angel investing started as advisor relationships.

I probably had half a dozen. I would lean into it, help them raise money as a second time founder. I knew a lot of VCs. Let me help you find your downstream capital.

I became more active than most of the largest investors in the cap table because I felt the other side. That became the way that I've operated and continue to operate. Along the way in 2019, I started writing angel checks. I was an angel in a company called Deal, which people know about.

I was an angel investor in a company called Finch. There's a company called Converse AI that has done very well in the AI staffing space. It's all very network driven. And now the word of mouth is out where people know, Charmant's not the type of person that just writes a check.

He's going to be there every step of the way. He can lean in if you want it. And if you don't, be happy to step back and take a back seat and help you just be on the sidelines. And so that's how the angel investing and angel funds got started.

speaker-2: 2023 launched Recall and could have joined an existing fund. Why did you end up starting your own? speaker-0: Still a question that I continue to ask myself every day. The jury is still out.

There's a difference between angel investing versus running a fund. Running a fund means portfolio construction, having ownership, writing larger checks. I've always felt when I was running the angel fund that if I actually had a larger fund, I could do it. A lot of the thesis was...

I'm going keep on doing what I'm doing. Now there's a tailwind around AI. For me, it was this passion of there's a need in the market to actually be a really strategic part to a B2B founder when they have nothing. What was interesting is even the most experienced founders know that you're starting a B2B company.

The only thing that matters is revenue and product. It's hard out there. Think about the last 10 years when I was a founder twice, all of these sales engagement as a category did not exist. And now it's like really hard to capture the attention.

How do you have a partner that's going to break through and help you break through the mold? A lot of folks have a network, but to actually be a partner to say, Hey, I'm going help you build pipeline. I'm going to help do events with you. I'm very passionate about that domain.

This is the time. And now with AI, everything looks the same. How do you break through? In 2023, I had no idea.

You said, Hey, do you know any LPs? I'm like, I don't know what you're talking about. Institutional LPs, fund to funds. I had to learn the hard way.

As I learned about myself, I leaned into what am I good at? What is the need in the market? And how do I play to my strengths versus chasing the next thing? We are a collaborative fund that invests at the inception round.

And we are not targeting high ownership. We're targeting high ownership relative to our fund size. To them, 3 to 5 % is not a lot, but for our fund size, that allows me to create a sort of 10x fund. And so I asked myself, what do founders need?

I'm not the brand that helps them hire recruits, but outside of the brand and capital, the second thing they need is help to go build their business and particularly get them in front of prospects, customers, and someone who can help them in every step along the way. Most founders have never done sales. Most founders have never ran marketing. Most VC funds, the partners have never ran those functions in a B2B context and have also done it as zero to one and has also been a founder.

So when you put all these things together, our pitch to founders is like, hey, listen, You need someone to help you get from where you are today to get your early customers. And you need someone who's not only just doing it for you, getting those doors open, but more importantly, when you're stuck, who do you call to unstuck yourself? And whether it's I'm stuck in a deal, my pipeline is dropping, the tactics that I'm using are not working. What do I do?

Who do you talk to about that? Most folks say, let me refer you to someone, but shouldn't that be an area that your VC fund should help you with? And so a lot of founders that want me on their cap table know that I'm going to help them get some early customer intros. And a lot of cases of the investments that we do, this is not true in every market.

I get this unique benefit personally, where I get to use all the technology and tools, you know, I think sometimes VC is kind of like, The game is changing on the field, but I'm on the field just alongside with them using all the AI tools. I think networks get stale. What's great is whenever I do an event, I meet new people. Therefore my network never gets stale because I'm constantly meeting new buyers.

In a lot of ways, I feel like I'm winning when I do this work. I'm creating more value for other portfolio companies because my network is continuing to evolve, let alone our LPs that back our fund. speaker-2: Is that part of your diligence? Do you offer customer introductions before you?

speaker-0: I remember one of our investors who I learned a lot from his name is Joe Krause. He was a Google Ventures for a long time. He's the president of Lime right now. He said this question to me, which is like, in the absence of data, what do think we should do?

It's still very conviction based. Sure. I can make an intro, but the buyer I make an intro may not be the best buyer for them. May not be the best person.

There's a lot of things that factor whether the signal tells you something. I still go on conviction on is this a prop? What business problems is this company solving? How big is that business problem?

How hairy of a problem is this? A must have versus nice to have, you know, and how are they going to do it better than anybody else? These are fundamental questions that I care about. One customer intro prior to making investment doesn't really mean anything because it's just the end is one.

speaker-2: For fund one, you built it with your wife, Sarah. both studied at UT Austin together 25 years ago, and she spent six years at Scale AI as journal counsel. What was it like building a fund together? speaker-0: Sarah's the best, not only because she's my wife, but she is incredibly bright.

She's incredibly networked. I'm very fortunate to have someone like her in my life, let alone have the opportunity to partner with her in a business capacity. We've always been angel investing. In some ways, doing this fund was just an extension of what we were doing.

It's weird living in Silicon Valley when we're both in tech. Because our entire life is around this, this work. She was at Dropbox 15 years ago. She was the first general counsel of Plaid.

She was at Scaly Eye. We've just been around, right? So it's like, how can you not talk about markets and ideas and founders and people we know starting companies? Everybody wants to recruit Sarah.

She's my wife. We made a calculated decision in mid-stage in fund one that her skill set. which is highly specialized being an AI expert in the context of legal to go back in house. I don't think she's shared where she is quite yet, but it's a very hot AI company.

The networks that she's a part of becomes a superpower in our sourcing. People know the Neoghies in some form, whether they reach out to Sarah or me, or then they somehow get to Sarah. Sarah has been around a lot of board rooms in the context of Plaid, Scale and Dropbox. A lot of our LPs are.

early execs, the Dropbox, Plaid, Ferry and Gusto. We lean into our networks, not only in terms of helping jumpstart our fund, but also the networks of founders that we ended up backing. speaker-2: Fun 1 is 14 million, Fun 2 is 25 million. What's the jump from 14 to 25?

speaker-0: When a lot of LPs talked to us about fun one, the questions are the right questions. Hey, can you write a larger check? Can you get more ownership? And the experience that we've had in the last two and half, three years doing this full time was that the answer is absolutely yes.

For fun too, we are going to write larger checks. Our average is around 400, 500 right now. We're going to be writing 600 to 900 and fun too. We know we can get more ownership.

have founders asking us, like, can you lead or can you write a larger check? We have to maintain our commitment to our portfolio construction and fund one. For fund two, let's lean into it more. Try to get more ownership and maintain a diversified portfolio of about 30 to 35 investments.

You go to our website and we have 60 video testimonials. Most VC funds don't have video testimonial funding about what is a fund done for you. The plan for fund two is to raise a 25 million dollar fund. Maintain doing AI applications where we think we're at the early innings of what we've seen in cloud 20 years ago.

This is a bigger transformation in what's happening in technology. I'm excited to be part of that adventure over the next decade or two. speaker-2: And talking about the founders, let's shift here into the thesis, the founders that you actually invest in, you focus on AI native companies, re-imagining enterprise systems. But what does being AI native really mean to you and what's your take on the bubble?

speaker-0: I invest in software applications, the future of work. When I look at AI native, like I'm looking at founders that are looking at what is the business problem you're solving. How can AI transform the business process or workflow? How can those workflows kind of compound to get to a hundred million gross profit?

We happen to have kind of core theses. One is we think that there is going to be a complete disruption of cloud legacy SaaS. What do we think of the top companies, whether public or. private equity owned, we think that in five years it's going to be a completely different stack.

CRM, ERP, accounting, you name those stacks, it's going be a completely different company. We have a bet on certain aspects of vertical markets. The front office and back office is going to change specifically a lot of manual labor that can be done through AI. The most obvious kind of examples of this is front office work, answering calls to triaging.

see what's happening in customer support. And a third area is services software bet. Rather than selling software to buyers, sell the outcome. We think there's going be different types of services businesses.

Accounting firms happen to be a great example of this, where you're going to see accounting firms that are going to have really technology behind the scenes that are going to start doing a lot of the work that accountants were previously doing. We have this macro thesis of the types of companies that we're excited about. In terms of the bubble, I don't know. It's still too early to tell.

Some of it's merited. Some of these companies are getting real revenue traction. This is not like 2021 where it's just frothy stuff. There are real companies that are getting real revenue traction very, very quickly that merits the valuations that we're seeing.

But there's also the opposite. We're seeing kingmaking happening. I ended up writing a post about this where there are certain categories that I think multi-stage funds are saying, Hey, this category is meant for disruption, regardless of traction. let's put a bunch of capital against the founding team.

And before you know it, they raise A series B very quickly at valuations that are inconsistent with the fundamentals. Founders that agree to taking that capital have to own the outcome. We've seen what happened post 21, where there were down rounds, the jury's still out on those types of companies. This is also a symptom of the fact that the funds are getting larger.

The multi-stage funds are now, you know, previously a billion dollar fund, now sort of six to $8 billion, they just have to deploy. But I don't blame those founders either. Like if someone says, hey, I'm going to give you a hundred million dollars. You only live once.

If you think you can do it, then do it. Go lean into that 500 million valuation with your 200K ARR. I'm not foolish to the notion that most founders will always prefer the multi-stage fund because it's like getting into MIT or something. This is going to carry me for the next two decades.

And I understand that, but now if you take it, you got to own it and grow into the valuation that you just signed up for. I don't really think there's some aspects that's probably a bubble, but there's also some real fundamental opportunities we're seeing that are really impressive at the business fundamental level. speaker-2: And as we come to a close, we're going to shift gears a little bit and get a little more personal. What do you think's been the hardest part about building Recall?

speaker-0: I think the hardest part has been just doing it all. I had a friend of mine email me last week and he's like, oh man, you're this fancy VC. And I was like, what are you talking about? There's nothing fancy about what I do.

I'm the web master investor relations, the investor, the analyst. I literally am doing all the functions. There's real accountability, running LP memos, communicating, fundraising. Every LP has different expectations, but The biggest thing that I've learned is the math of the fund.

To create returns is not easy. I think LPs have a really hard job picking among A versus B versus C, the stories that the people share. I choose to stay small because that gives me a higher chance to create a higher returning fund. And that's strictly the math of it all.

I think most founders, if I ask them, hey, Do you understand the math of venture capital? Most will say they don't really know. That's a problem. I think there's a lot of education that needs to be done in this market for founders to really say, hey, here's what it means to take venture capital.

speaker-2: question for me. You obviously operate at a place where most species won't touch and you also have the edge of having founded companies and an operator as well. Everyone gives capital and everybody gives intros. That's a pitch that we hear quite often from different emerging managers.

What do you think that you're doing that founders can't get anywhere else? speaker-0: What we try to do is consistently show up and create value in a revenue oriented mindset every single month until they get to the next round. That sometimes is directly in the context of, let me go build pipeline. Some of that is also saying, hey, you have pipeline, let me help you close it.

Which is a whole different art than most VC funds don't play in. How many VCs do you know ran enterprise sales? actually knows playbooks, understands methodology, understands tactics to use in certain situations. Most founders have never been classically trained.

Well, let me help you unstuck an opportunity. Hey, I got the situation. Let me describe it to you. I actually do sales coaching as though they're hiring a professional sales coach.

Maybe that's not the need in month one. It's like, Hey, let me get some meetings. Maybe month two is now I'm stuck in stuff. Maybe three, I got pipeline and now I got to close it.

And then I got to go back again. I do it all over again. It evolves. So it's that consistency of engagement that really matters for a founder.

And they can account me on it. The number of times founders text me and say, Hey, can I talk to you today about a deal that I'm stuck in? Not my regular monthly check-in. That's way too late.

One of the tactical ways we have programmatically done this is through events. We do a lot of events for our founders where they say, Hey, I want to meet more buyers in this persona. And I'm like, great. Tell me who you want to outreach.

I will start doing outbound and I'll fill the room. I love it. I meet new people. I facilitate the evening conversation.

I've done this in the context of CPG. I've done this to first in front of finance leaders. So it's kind of those programs that we actually run, not only in terms of sales coaching, intros, doing personalized buyer dinners, it's the collective value that is really what founders are gravitating towards. speaker-2: Thank you so much for your time today and for joining us on the SlicePod.

speaker-0: I appreciate the opportunity. Thanks for taking time and hearing it all out. speaker-1: And you've just listened to yet another amazing episode of the slice pod hosted by Sunwoo and produced by Sunwoo with a brief appearance by me, Fabri. Next week, we'll talk to another former founder turned angel investor now based in Berlin.

So we're going all the way across the pond. Don't miss it. Subscribe to the pod on Spotify, Apple podcasts or wherever you listen.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • How Fortune 500s Use Procurement to Manage Vendor AI Training Data RightsEnterprise Tech with Fexingo · on Salesforce90 / 100
  • Why revenue growth breaks down (and how great companies fix it) with Dan Bernoske If Prices Could Talk · on Salesforce89 / 100
  • Why B2B Brands Fail at Account Based Marketing AttributionThe Marketing Operator Podcast with Fexingo · on Salesforce88 / 100
  • #410 - How Mazy Dar found room in Google and Microsoft's market - and won the world's biggest banksThe Remarkable SaaS Podcast · on Salesforce87 / 100
  • How to Sell Against a Competitor Already in the BuildingSales Leadership with Fexingo · on Salesforce85 / 100
  • Why B2B Brands Are Using AI for Account PrioritizationThe Growth Operator with Fexingo · on Salesforce84 / 100

More from slice podcast

All episodes →
  • carmen alfonso rico / cocoa ventures78 / 100
  • suds sridharan / sf167 / 100
  • helena gagern & teddy schaumburg-lippe / embassy ventures56 / 100
  • daniel ha & gadi borovich / antigravity capital67 / 100
  • matt curtolo 81 / 100
Explore the best B2B HR podcasts →
All slice podcast episodes →