Keep Going

John Biggs
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When you're going through Hell, keep going." This is a podcast about failure and how it breeds success. Every week, we will talk to amazing people who have done amazing things yet, at some point, experienced failure. By exploring their experiences, we can learn how to build, succeed, and stay humble. It is hosted by author and former New York Times journalist John Biggs. Our theme music is by Policy, AKA Mark Buchwald. (https://freemusicarchive.org/music/policy/) www.keepgoingpod.com

  1. Keep Going: Identity Collapse in the Age of AI

    23H AGO

    Keep Going: Identity Collapse in the Age of AI

    On this week’s episode of Keep Going, I spoke with Patricia Martin, writer, researcher, and author of Will the Future Like You? She has spent a decade studying what happens when failure is not just professional but personal. The kind that makes you wake up and ask, who am I now? Patricia calls it identity-threatening failure. Not every setback qualifies. Missing a target or losing a client stings. But when your business is your baby, when your persona is fused to your public presence, when your work becomes your self, a collapse can feel like rejection at the level of love. The brain codes it that way. Cortisol rises. Adrenaline spikes. Dopamine drops. Executive function weakens. You feel empty, hypervigilant, unmoored. Entrepreneurs are especially vulnerable. We are taught to invest identity in what we build. In the attention economy, we perform ourselves across platforms, post after post, video after video. The persona gets muscular. The inner self gets quiet. Patricia calls the result “persona fog.” We externalize the self so thoroughly that when something breaks, we do not know what remains. What struck me was how physical this all is. This is not motivational poster talk. There is a somatic reaction to identity collapse. A rewiring. Some people pivot sharply. A tech founder goes back to the family farm. A software executive returns to the factory floor. Not because they failed, but because they need ground again. So what do you do if you cannot escape to a dairy farm? Patricia argues there is no hack. There is practice. First, discernment. Identity failure scrambles executive function. You lose clarity. You must relearn how to hear yourself. Second, reflection. We have lost the muscle of self-reflection. There is no app for the inner world. You have to sit with the question: what is this doing to me? Third, confirmation and witness. Own what is happening. Say it out loud. Find someone who can remind you who you were before the fog rolled in. As we talked, the conversation turned to AI, to coders who fear obsolescence, to journalists wondering what work remains. Patricia’s answer was not comfort. It was responsibility. You must know who you are. You must identify what you bring that cannot be replicated. Creativity. Imagination. Sentience. The ability to feel and transmit meaning. Machines can perform. They can flatter. They can automate. They cannot enact being. We are entering what she calls an age of hyper reinvention. Pivots will not be rare events. They will be routine. That means resilience can no longer be grit alone. It has to include an active relationship with the unconscious, with creativity, with reflection. There is a line Patricia shared that I keep returning to. Every defeat of the ego is a victory for the unconscious. In a culture built on dominance and performance, that feels radical. The question is not whether the future will like you. The question is whether you can hear yourself clearly enough to survive it. Transcript Welcome back to Keep Going, a podcast about success and failure. I’m John Biggs. Today we have Patricia Martin. She’s a writer, she’s a podcaster, she’s a researcher, and she’s recently wrote a book. It’s coming out soon, Will the Future Like You? Which I’m afraid to hear the answer for, so welcome, Patricia. Patricia (01:26.852) It’s a pleasure to be here, John. John Biggs (01:28.942) So you’re an old hat at podcasting. You’ve been doing this for quite a while. A million views on your stuff. I want you to welcome to mine. And I’m actually really happy you’re here because this book sounds fascinating. Why don’t you just give us a quick recap about what you wrote. Patricia (01:45.167) So I researched this material in the book for 10 years. And I entered into the research originally to understand the impact of the digital age on the human psyche. And I encountered not only a variety of people and their stories, and then also, you know, as an entrepreneur myself. I underwent a massive change in my life and in my business. And I woke up one morning asking the age old question, who am I? And that is when my research took a fresh direction. And I began focusing on what it means to lose and rebuild identity in the digital age. John Biggs (02:34.144) Mm-hmm. So you were talking earlier about the identity destroying failure. I guess reducing failure, right? A failure so poignant that it changes essentially your entire life. So tell me about that. Patricia (02:49.378) So not every failure that we have affects us at an identity level. What tends to happen though with entrepreneurs, and I would say this is generally a cultural issue for Americans, is that we invest a lot of identity in what we do. Entrepreneurs more so because it’s your baby, it’s your creation. You’re doing something, usually it can be out of a passion or you’re addressing a need in the marketplace. But it is something that you have spotted and you internalize as part of yourself. So what happens when we fail at an identity level, especially in the attention economy, is that we begin to recruit differently from the interior world of ourselves. So let’s say, for instance, you have somebody who has built an online business and they’re an influencer. That is persona heavy identity. And the persona is the weakest part of the psyche. It has never been, it was never designed to undergo the garrulous rigors of online life, right? And yet we’re pounding it day after day, post after post, video after video. And so when something goes awry there, there are some specific things that start to happen. when we tip that into an identity problem. So first of all, it’s a social neural pain. We treat that failure as a rejection, just like we would treat it as a love rejection. And that’s how the brain codes it and the body feels it. The other thing that happens is it’s probably not a surprise that we get a cortisol rush from that kind of failure, but it has a lingering effect. Probably I think the most intriguing thing that came out of the neuroscience is the amount of adrenaline that courses through the body during a failure that is specific to the loss of identity. So it’s as if we are now hyper vigilant to find our sense of self again and we begin the search to recruit back the sense of who we are. Patricia (05:10.536) And so that has an effect that is, you know, and your dopamine goes low. So now you’re operating on cortisol, adrenaline, and low dopamine. So it’s kind of a perfect storm for feeling really empty, lost, stuck, disconnected. So, you know, you’ll talk to people who have had a failure like that. And it requires in the attention economy more than just grit. Because it’s moving so fast, you’re not just, you know, pulling yourself back up by your bootstraps and standing back on your feet. Back on what? What ground? The territory is moving so fast. So this is where you find people tend to tumble out. You’ll also find people at this point sometimes will take a sharp pivot. I talked to people who went from running software companies to working in their father’s box factory. One woman was in a tech startup that got really big. She sold it, and she went back to running the family dairy farm. So it was kind of like they needed an antidote to kind of clear themselves. some of these were success stories. But what was interesting is that some of them didn’t go back to the hurly burly and the grind of something that was as intense. as an online business. John Biggs (06:38.67) So I love that you’re able to codify this and describe it in a very clear way. think a lot of people have that. I mean, first off, a lot of people have that fantasy, right? I think that every single Hallmark movie is about that, where you go back to the small town and you become a dairy farmer after having a hard business, like a hard charging business life. So I think the primary question is, you’re in that mode, once you end up failing out of it, out of an entrepreneurial situation, you described the persona being destroyed to a degree. from a layperson’s point of view, the persona would be just, I don’t know, just my day to day happy-go-lucky whatever. But it sounds like you’re talking about something a lot deeper here. what happens when that identity is destroyed? And how do we get it back, aside from working at a dairy farm? Patricia (07:30.989) Well, here’s the thing. Yeah, because we can’t all do that, right? And some people genuinely like to learn and ladder up. Failure, success, failure, success. I think, though, what’s important to understand about the difference between a more linear type of set of milestones in one’s career and the matrix of what we’re experiencing now. So pivots and turning points happen more frequently. I think we’re going to see with the rise of AI, that is going to become an annual event for people. I’m just putting a pin in that. We’re going to be pivoting more and more and more. And so I think the problem with the internet age is it has made us externalize the self. So, you know, there’s no app for the inner world. We are always out there. We’re always on. We’re always pushing content. And we’re dividing our sense of self across multiple platforms and multiple personas. So when we’re externalized like this, we’re vulnerable. We’re vulnerable to the kind of change. the kind of failure that we’re talking about that have real bodily consequences and psychological consequences. So I would say the plague of our time is something I identify in the book as persona fog. And what happens is that when this gap opens between the true self and the externalized self, we’re no longer in search for the self. We’re performing a self. That’s a very different proposition. The self is at arm’s length to begin with, also making us vulnerable. And so when we take a loss and we’re in this fogged state already, first of

    25 min
  2. Keep Going: What to Do When the Bottom Falls Out

    MAR 2

    Keep Going: What to Do When the Bottom Falls Out

    Kevin Gaskell walked into a room expecting to be fired. Instead, he was handed the keys to Porsche UK. That moment says a lot about his career. He is an engineer by training. Then he added an MBA. Then accountancy. Blueprint and balance sheet. He joined Porsche in his twenties, rose through operations, and found himself in a company that was sliding. Three years of unsold inventory. Brutal headlines. Public jokes about pigeons and deposits. He thought he was getting a ten minute exit interview. He stayed for four hours. He told the owners exactly what he thought. What to cut. What to fix. Where to aim. He expected consequences. He got promoted. Five years later, Porsche UK went from last to first. That sounds like a clean arc. It was not. They cut costs by 50 percent. They simplified. They endured press attacks. They carried the weight of three years of unsold cars. That is not glamour. That is grit. Then he did it again at BMW. Then he quit. This is where the story turns. He left one of the best jobs in European automotive to build Cars Direct Europe. Rented office. Desk. Phone. Two young kids at home. American backers. Big plan. Six months in, the investors pulled out. Gone. Now what? No salary. No bank support. No track record as a founder. Just a business plan and three colleagues. This is the part people skip. The terror. The mortgage. The silent nights staring at the ceiling. They negotiated a sliver of funding. Raised money from friends and family. No safety net. Then they pivoted. Consumers were not ready to buy cars online. So they went after fleet operators. Boring. Back office. Massive inefficiency. Two hundred people on phones sourcing cars. They built a platform. They became the backbone. They prepaid dealers with token systems, which quietly funded their growth. Five years later they sold for nine figures. That does not happen because someone is lucky. It happens because when the bottom falls out, you do not flinch. Kevin talks about luck. He was in the right room at Porsche. That is true. But courage matters. When you think you are about to be fired, you can shrink. Or you can speak clearly. He chose clarity. There is another thread running through his story. He does not build fragile companies. He stays five to eight years. He builds teams that can run without him. He does not asset strip. He builds foundations. Today he runs multiple companies in parallel. Fiber networks. Data platforms. Investments. He has rowed oceans. Walked to the poles. Climbed mountains. That part is dramatic, but it is not the point. The point is this: failure comes first. Success is the fight that follows. When the press mocks you. When investors leave. When no bank will return your call. That is the test. Do you believe in the thing? If the answer is yes, you keep going. That is the through line. Not hype. Not trends. Not whatever the market is excited about this week. He is openly skeptical of herd behavior in investing. Dot com. AI. Railways. The pattern repeats. Tools matter. Products matter more. Service matters most. Build something real. Tell the truth about where you stand. Simplify. Cut what does not work. Double down on what does. And when you think you are about to be shown the door, speak up anyway. You might walk out unemployed. Or you might walk out in charge. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

    22 min
  3. Keep Going: Social Capital Is Still Capital

    FEB 23

    Keep Going: Social Capital Is Still Capital

    I sat down with Constantin Kogan last week after we randomly met in Salt Lake City. We both live near New York. Sometimes the universe has a sense of humor. Konstantin is the founder of Holistic Capital, a multi strategy investment firm focused on digital assets. He also runs a podcast called Holistic Investments. Over 100 episodes. More than 600,000 followers across platforms. Not bad for something he started during COVID while stuck at home. But the interesting part of his story is not crypto. It is not Bitcoin in 2012. It is not Ethereum in 2016. It is not being early to hedge funds or registering with the SEC. It is this: social capital is capital. During COVID he found himself in a tough place. Like most of us. No travel. No meetings. No momentum. He asked a simple question. What can I do that I actually enjoy? His answer was long conversations. Honest conversations. The kind you have in a kitchen at midnight over wine. So he started a podcast. No monetization plan. No big strategy. Just curiosity and discipline. For five years he made nothing from it. Most podcasters quit before episode thirty. He kept going past one hundred. Why? Because he was not optimizing for money. He was optimizing for relationships and learning. That changes everything. We talked about failure. I asked him about bad trades. Crypto winters. Market crashes. He surprised me. The real failures were not financial. They were relational. Picking the wrong partners. He described business like a marriage. You can survive small disagreements. But when a real crisis hits, that is when character shows up. Do you share a vision. Do you share values. When it gets ugly, does your partner protect the mission or protect their ego. You cannot really test that in advance. There is no checklist. No personality quiz that guarantees success. At some point you rely on judgment and instinct. And you accept risk. That is uncomfortable. But it is honest. We also talked about investing. Early in his career he focused on technology and timing. Now he looks at people first. Ideas are abundant. Execution is rare. Motivation varies wildly. Some founders want status. Some want money. Some want to prove themselves. Some want to change the world. Only one of those types will survive when things get hard. If you are building something, remember this. Investors are not just evaluating your deck. They are evaluating your stamina. Your alignment with your team. Your ability to handle conflict without blowing up the room. And if you are thinking about starting a podcast or some other media project, understand what you are signing up for. It is a business. It consumes time. It demands consistency. It does not pay right away. Maybe not for years. But it builds something else. Reputation. Network. Intellectual capital. A record of your thinking. That can compound. Konstantin does not even call himself a VC anymore. He trades liquid markets now. Algorithmic strategies. Volatility. But the podcast still runs. The network still grows. Yesterday he met the co founder of Venmo and invited him on the show on the spot. That is how opportunity works. Quiet compounding. Relationship by relationship. You cannot fake that. You have to show up. You have to publish. You have to keep going when the numbers are small and the monetization is zero. There is a lesson here. Build things that create optionality. Build things that connect you to other capable people. Build things that make you better at thinking and listening. Money follows. Sometimes slowly. Sometimes indirectly. But it follows. In the meantime, protect your partnerships. Choose carefully. Align early. Agree on how you will handle conflict before it arrives. Because markets rise and fall. Technologies shift. Cycles repeat. Character does not. TRANSCRIPT Welcome back to keep going. A podcast about success and failure. I’m John Biggs today on the show. We have Constantin Kogan. He’s the, uh, GP at holistic capital. And you also have a, really cool podcast, which I’m going to be on eventually. So I get to actually, Constantin Kogan (01:18.537) Mmm. John Biggs (01:37.954) meet your audience. But we met just a week ago and you have a really, cool story. So tell us what you’re up to, Constantin. Constantin Kogan (01:47.235) Hi, John. First of all, an honor to be here. Yes, we met in Salt Lake City out of all the places, ironically, live in close by in New York. I don’t know where to begin the story. guess maybe just a little bit of background. I’m originally from Ukraine. was born and raised there, 11 years in the United States. I started my career as a... John Biggs (01:56.236) Yeah. Constantin Kogan (02:12.651) I’m a modernism future trader. Chicago Bota Trader was my first venue where I started to explore financial markets. From there, went through a hole and bought my first 5 Bitcoin in 2012. 2016, I a conscious choice to go all in when Ethereum got out and... thought that programmable money is definitely going to be the future of tokenization of all the assets. 2017, I became a partner in the first crypto fund of hedge funds in the world. We’re the first SEC registered firm. And from there, you know, I had a wild journey co-founding three companies, you know, investing in 80 plus venture startups and running my own. you know, my own hedge fund, working for hedge funds and now focusing on holistic capital, which is basically a multi-asset, multi-strategy investment firm, mostly focused on digital assets, but eventually we will work with different assets on blockchain as well, which I think that’s where the future is going to. And also, as you mentioned, I... also run Holistic Investments, which is the podcast which I started during COVID time. My first guest was Dan Moritz from Pantera Capital because we invested in Pantera so we good relationships with them. Since then, I 100 plus guests on my show and enjoy learning from incredible individuals. John Biggs (03:49.278) And you’ve got you got like 600 plus thousand followers across your across all your platforms. What do you think led to that level of success? And what is what does that give you as a VC? Like I know what this gives me as a I don’t know, just a putz on the internet. But what does that give you as a VC? Constantin Kogan (03:55.957) Yes. Constantin Kogan (04:10.313) Well, to be completely transparent, I don’t consider myself as a VC anymore. Like I used to be. Right now I’m... mostly with trading more liquid assets, right? So you can think about it as algorithmic trading firm, high frequency trading, right? Closer than, so I used to be at VCN. I thought that was incredible opportunity in emerging markets, right? But regardless, what it gives me, it gives me network. I think... Social capital is another form of capital, right? Not necessarily like people who invest in you is your, you know, main business partners in life. You know, some people like stay with you regardless of whether you succeed or you fail. And I think the more value you bring to other individuals, like what look what we’re doing today, right? You’re the first who allowed me to be on your podcast, which I’m very grateful for, and then you’re gonna be on mine, and that’s hopefully gonna inspire others to do the same and share thoughts, you know, learn from each other. I would say intellectual capital and social capital, that’s what’s the primary goal for me, and that’s how I’m giving back to the world by educating the future generations. John Biggs (05:28.396) Mm-hmm. So tell us about the growth of this media empire, I guess you could say. So you started out just deciding to do this. What was the impetus? Why did you want to do it? Constantin Kogan (05:40.105) Well, media empire, it’s a big word. love how you frame it. Future media empire, yes. Yes, I appreciate it. Look, I, again... John Biggs (05:47.03) Yeah, we gotta tuck each other up, yeah. Constantin Kogan (05:54.363) Wholeheartedly, was in a very tough spot during COVID. I think it was a very challenging time for everyone. And I thought to myself, what can I do? I mean, we’re sitting at home. There’s not much to do. you know, everything is digital anyway. You cannot go out. And I started to ask myself, it was more of a soul searching exercise. Like, what can I do to at least do something what I love to, you know, have a cohesive discussion and also somehow impact others to inspire them or to help them in some way and that podcast format was the most relevant for me. I’ve listened to a lot, I’m a big fan of know like Joe Rogan, Alex Hermosy, know and Alex Friedman and many other like greats know people who went bold and started to invite other individuals, have long discussions with them so my My format is about 60 minutes, right? So it’s enough time to learn about a person, about their journey, about where they’re coming from, and also how they achieve this success. And also ask them uncomfortable questions, which allows to bring less controversy, but more about what were the failures? What are the learning lessons? Something that you would not talk on your board meeting or somewhere in the traditional media, right? So more like honest, friendly conversations, you will have when you’re drinking wine with your friend in the kitchen. John Biggs (07:30.606) So tell me about some of those failures. think you, I mean, right now we’re looking at a crypto winter. So that sounds like, it sounds like you might have some issues right now, but tell me about the failures as you move through and try to enter this space. Constantin Kogan (07:44.255) Yeah, as a matter of fact, we’re doing great. maybe we like when you’re trading. the market is a strategy, you’re not like long like any asset like we’re making money even shorting right now. So for us, the volatility and big spikes is where we make most of our money. And that’s the exciting part. Like, and that’s when I finally un

    17 min
  4. The Innovators: Why AI Still Needs Humans

    FEB 18

    The Innovators: Why AI Still Needs Humans

    On this episode of Innovators, I spoke with Jason Ambrose of People.ai about what “agentic AI” actually means, why sales data is messier than most people think, and why blindly trusting large language models is a mistake. People.ai has been around long enough to see multiple waves of enterprise software come and go. Now it’s repositioning itself squarely in the agent era. Most CRM systems tell you what was entered. They don’t tell you what’s actually happening. People.ai takes a different approach. Instead of relying on manual updates, their AI analyzes the communications that define modern sales, emails, Slack messages, meetings, chat transcripts. The system maps that activity to accounts, contacts, and opportunities. That sounds straightforward until you scale it up. If you’re a startup selling to a small business, maybe one salesperson is talking to one buyer about one product. That’s simple. But when Microsoft sells to Verizon, you might have dozens of people on both sides, across legal, technical, procurement, and executive roles. Conversations happen everywhere. Mapping that complexity into a clean CRM record is hard. That’s where People.ai claims it shines. It uses its own AI models, trained on billions of transactions, to reconstruct what’s really going on inside a sales organization. What Is an Agent, Really? We talked about the shift from chatbots to agents. A chatbot answers a question. An agent has an objective. Jason framed it in terms of business process automation. Old-school automation works when the logic is predictable. If this, then that. Stay inside one system, follow a defined workflow. Agents step in when reasoning is required. They cut across systems. They pursue a goal. They have to decide what to do next. But that only works if they’re plugged into real expertise. Jason made a useful distinction. Public LLMs are trained on public data. Enterprise expertise lives in private systems. If you want an agent to act intelligently inside a company, it needs access to proprietary data. That’s a big trust ask. You’re effectively saying, “Let our AI read your emails.” That’s not a small decision. Avoiding “Build Trust With Stakeholders” Anyone who has used a generic LLM for business advice has seen the problem. You ask for guidance and you get vague platitudes. “Build trust.” “Accelerate the deal.” “Engage the customer.” That’s not actionable. Jason argues that this is where expert agents come in. Instead of spitting out generalized advice, they ground recommendations in specific deal data. Who hasn’t responded in three weeks? Which technical blocker hasn’t been addressed? Where did the last conversation stall? Without that grounding, AI defaults to corporate fortune-cookie language. The Capital Markets Reality We also touched on fundraising. SaaS is being repriced. Public markets adjusted first, and private markets followed. Companies that once enjoyed premium multiples are now being reevaluated in light of AI disruption. Capital is flowing into AI-native plays. If you look like “just another SaaS company,” you need a credible AI story. If you genuinely sit at the center of AI transformation, you’re in a stronger position. People.ai is not currently raising, but Jason sees the shift clearly. The market is asking who is being disrupted by AI and who is using it to build something new. Is AI Replacing Jobs? It’s the obvious question. Jason’s take was pragmatic. Technology changes work. It always has. He remembers the early days of the web and the anxiety that came with it. Some jobs disappear. Most jobs change. His line stuck with me: people should work with people, and let AI do the rest. Sales, at its core, is still about relationships. AI can summarize, surface risks, and suggest next steps. It can’t replace trust, empathy, or judgment. At least not yet. If you’re in sales and you haven’t started using AI, Jason’s advice is simple. Start. Use ChatGPT, Claude, Gemini, whatever tool you prefer. Have it rewrite emails. Summarize meeting notes. Draft follow-ups. But don’t copy and paste. He pointed out something many executives are quietly thinking: if you send a clearly AI-generated email without tailoring it, you’re signaling that you didn’t invest the time. And if you didn’t invest the time, why should the recipient? AI can amplify your work. It can’t replace the part that makes you human. People.ai is betting that the future of sales is agentic, cross-system, and grounded in real communications data. Not just dashboards, but reasoning systems that understand what’s actually happening inside complex deals. Whether you buy that vision or not, one thing is clear. The next phase of enterprise AI won’t be about novelty. It will be about integration, trust, and measurable outcomes. And that’s a much harder problem than writing clever emails. TRANSCRIPT Welcome back to the Innovators show about amazing people doing very cool things. I’m John Biggs. Today on the show we have Jason Ambrose from People.ai. It’s agentic and it’s for sales teams, but why don’t you add to that, Jason, welcome. Jason Ambrose (00:24.482) Yeah, thanks, John. So what People.ai does is our AI figures out what’s happening in a sales organization by looking at the communications between your field and your customers. So we analyze emails, chat transcripts, meetings, Slack messages, and the like to turn that beyond just the data to what’s actually happening. How does that how do you find the answers of what’s happening in the organization? And we provide that either to humans or to agents. So that’s been our big shift this year is to realize that the stuff that we were doing for humans in CRM is also very relevant when you have agents trying to figure out what’s happening in sales. John Biggs (01:04.094) So let’s explain agents to folks who might not even understand what’s going on. So the idea originally was that you had a chat bot. You asked it something, and it responded to you. But now we’re talking about agents, which are supposed to be autonomous to a degree. So how do you guys describe those, and how do you use them? Jason Ambrose (01:24.086) Yeah. And hey, look, you know, I may not have everything right on this too, but at least the way that I think about it is maybe starting from a business process automation, right? So, you know, for, for periods of time when we had predictable workflows and we knew, you know, sort of if then else, there’s not thinking that happens there, but we could automate work if that had to happen. John Biggs (01:28.188) Mm-hmm. Yeah. Jason Ambrose (01:48.302) In the case of agents, that now becomes something where they have some chain of thought, they have some reasoning. So they know they have an objective or a purpose that they’re trying to work through. They have to figure out how to get that done. So when there’s a little bit more, you know, thinking, reasoning that needs to happen to figure out how to get that objective, that suits an agent. What I think we’re seeing with customers is they’re figuring out how to unlock that for work that needs to get done across a lot of different systems, right? So, know, BPA, business process automation, or what you have in your workflow tools that tends to say within the silo of a system from data to business roles to presentation layer to humans. When you start to cut across the systems, that’s where there’s been big opportunities for agents. John Biggs (02:37.214) So in this particular case, you guys are focusing on sales leads, that sort of thing. So you basically take every single data point that you have and say, this person, I don’t know, emailed you two weeks ago and also was tweeting this and is interested in this. So why don’t you give him a ring? Is that generally how it works, or what’s the? Jason Ambrose (02:56.376) That’s yeah, that’s really close. Yeah. I think the difference is, you know, let’s think about two different types of selling, right? you could be a startup and you’re selling to a small business. That’s, know, pretty much one buyer. So, you know, if you think about it in the context of CRM, you’ve got one salesperson. You’re selling to one buyer at one account and you’re selling one product that that is pretty simple to figure out, right? Where it gets more complicated is if you’re. Microsoft selling to Verizon just to pick two big companies. You might have 30 or 40 people or more on the Microsoft side. You might have 30 or 40 people on the Verizon side answering different technical questions, having different conversations about different elements of your business relationship and how you match those activities to records in CRM that represent, you know, here’s a person that we’re talking to, here’s the account that we’re talking to. you know, here’s the specific sales opportunity that becomes really hard to do properly. And that’s, that’s where we, that’s where we shine. And that’s where we have, you know, pretty large customers like Red Hat, Verizon as a customer and some others. John Biggs (04:09.712) Would you be able to still do this without AI? Would this exist if we didn’t have this kind of, I don’t know, synthesis, right? Jason Ambrose (04:15.798) It would be really difficult, right? So we have our own AI that’s applied to do the math to figure this out. And it’s learned from looking at billions of transactions over the years, right? The second piece, I think, is how you integrate or interface with other systems. So you mentioned the chat interface. So a human does want to do that, right? So we put this alongside sales opportunity record. If you want to get the full story, you can ask the chat bot, are the risks in these deals or what’s happening in this account? Now with MCP, that same type of interaction can happen from an agent to our system.

    11 min
  5. Keep Going: Building a Creative Business by Letting the Work Lead

    FEB 16

    Keep Going: Building a Creative Business by Letting the Work Lead

    This week on Keep Going, I talked with Chantelle Shakila Tiagi, the founder of Tiagi, a creative production and artist consultancy that works across fashion, beauty, and lifestyle. What struck me was not the scale of the work, which spans London, Los Angeles, and Mumbai, but how unplanned the entire thing was. Tiagi did not start as a master plan. It started as momentum. Chantelle came up through fashion and production, worked with a boutique agency, then went freelance because she needed a break. That break turned into opportunity. One shoot led to another. Porter Magazine. Big talent. Serious campaigns. At a certain point, the work was too big to pretend it was just freelancing. She formed a company not to build an empire but to protect herself. The structure followed the work, not the other way around. That pattern comes up again and again on this show. People imagine founders sitting down with a five year plan, a pitch deck, and a vision board. In reality, most businesses worth talking about start because someone is good at something, other people notice, and demand quietly grows until it cannot be ignored anymore. Tiagi’s model is simple in theory and hard in practice. Brands come with a brief. Sometimes it is detailed. Sometimes it is a single image. Tiagi builds the team. Photographers. Directors of photography. Set designers. Creative directors. Producers. Fifty moving parts, all of which have to work together. Chantelle described producers as conductors. The orchestra only sounds good if the right people are playing the right instruments. This matters more now, not less. We talked about the DIY turn in creative work. Ring lights. Instagram reels. Cheap tools. Anyone can make something now. The fear is that expertise no longer matters. Chantelle’s take was calm and practical. People always want the real thing. They want best in class. You can cut corners, but it shows. Quality reveals itself over time, especially when brands are putting serious money behind campaigns. The same logic applies to AI. We talked about virtual models, synthetic environments, and brands experimenting with fully generated shoots. Her view was not defensive. AI exists. Ignoring it is how you get left behind. Tiagi will use it where it makes sense, especially in post production. If AI can create a background instead of flying a crew to a beach, that can be useful. But the idea that all shoots will become synthetic misses the point. Production is human. It is logistical. It is relational. It is physical. AI cannot run an event, manage a crew, or solve problems on set when things go wrong. The more interesting part of the conversation came when we talked about growth. Tiagi looks big from the outside. Big brands. Big names. Multiple offices. Internally, it is small. Chantelle kept it that way on purpose. Contractors expand and contract based on projects. The core team stays tight. COVID reinforced this lesson. Many companies realized they were carrying internal weight they did not need. Tiagi leaned into being nimble. Boutique turned out to be an advantage. This is where the title of the show really fits. Keep Going does not mean keep scaling. It means keep moving forward without losing your footing. Chantelle was honest about the tradeoffs. She rarely produces shoots herself anymore. Her days are contracts, meetings, sales, and management. This is a shock for a lot of founders, especially in creative fields. You start because you love the work. If things go well, you end up doing less of that work. Her advice was blunt. You have to learn to love the rest of it, managing people, building careers, making decisions, and taking responsibility. Otherwise, you will resent the thing you built. What stood out most was her emphasis on doing good. Tiagi makes a point of supporting underdogs and bringing new talent into rooms with established names. That is not marketing copy. It is how they build teams. Access is power in creative industries. If you have it, you have an obligation to use it carefully. We also talked about being an operator. Chantelle now has to handle contracts, billing and legal details: the unglamorous parts. Chantelle likes that work. Producers have to. It is a thankless role. You only hear from people when something breaks. But when a massive project comes together, when the shoot lands, when the team pulls it off, the satisfaction is real. The admin is the price of that feeling. There was no grand lesson at the end of this conversation. No blueprint. No hustle sermon. Just a clear pattern. Do the work well. Let momentum build. Do not grow faster than you understand. Stay small longer than feels comfortable. Accept that success will pull you away from the thing you started with. Decide whether you are okay with that before it happens. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

    16 min
  6. The Innovators: Making AI Pay Its Own Way With Lava Founder Mitchell Jones

    FEB 11

    The Innovators: Making AI Pay Its Own Way With Lava Founder Mitchell Jones

    On this episode of The Innovators, I sat down with Mitchell Jones, founder of Lava, to talk about one of the least glamorous and most urgent problems in AI right now, getting paid without going broke. Mitchell is building what amounts to billing infrastructure for AI products. If you are running agents, LLM powered tools, or anything where compute costs change by the minute, you already know the problem. Traditional payment systems were built for flat subscriptions. AI is not a flat subscription business. Lava sits in the middle. It routes AI model calls through a gateway, tracks real time usage and cost, and lets companies price that usage in a way that actually preserves margins. You can choose how much you want to make per action, per credit, or per customer, and Lava handles the rest, including paying through to the underlying model providers. What makes this urgent is something most founders are only now learning the hard way. In AI, your best customer can be your worst customer. Power users can quietly rack up massive compute bills while paying the same monthly fee as everyone else. That model worked in SaaS. It breaks fast in AI. Mitchell’s insight is simple and hard to argue with. AI behaves more like a utility than a software license. Utilities are metered. SaaS pricing is not. Lava exists to close that gap. We also talked about where the company came from. Mitchell has spent his career deep in payments, running Facebook’s digital wallet in emerging markets and founding a prior fintech company before starting Lava earlier this year. He did not wake up one day and decide to build an AI company. He talked to customers. Over and over. When everyone said they were duct taping Stripe together and hated it, he knew there was a real problem. The conversation also veered into founder advice, especially for people outside the usual tech pipelines. Mitchell grew up in Dayton, Ohio. His path ran through finance internships, late CS coursework, Dropbox, Facebook, and then startups. His advice was consistent throughout, do not stare at the top of the mountain. Focus on the next step. Compounding effort matters more than pedigree. Lava has moved fast. The company landed its first customers within months, raised a $5.8 million round, and now works with AI startups and legacy companies trying to shift from flat SaaS pricing to usage based models. If you are building anything with AI under the hood and have felt that creeping sense of dread when the compute bill hits, this episode will feel uncomfortably familiar. You can check out what Mitchell and his team are building at lava.so. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.keepgoingpod.com/subscribe

    20 min

  7. FEB 9

    Keep Going: From Corporate Storyteller to Remaking the Story of Anne Frank From a Southern Perspective

    I caught up with Marcos Bravo, a Chilean guy living in Portugal, who has spent most of his adult life bouncing between tech, sales, marketing, and whatever paid the bills. He is 46 now. He has a family. And he is in that phase where you look at your work and ask a blunt question: Is this all I am showing my kids, that life is just paying bills. Marcus is not doing the clean midlife pivot. He is doing the messy version. He wrote a book because he had time, he was unemployed, and he needed to put the stories somewhere or he was going to lose his mind. He got the idea after seeing a tweet about how, with everything going on, we might see another Anne Frank “in our backyard.” That stuck with him. He started writing a kids book, got blocked, then wrote a different story that took shape. It became Ana Luz’s Diary, about a girl named Anna hiding in an attic with her brother and aunt, trying to stay quiet because noise brings the wrong people. He ran it past his daughter, she signed off, and he shipped it. At the same time, he is doing video work for companies because that is what keeps things running. He is starting an ice cream brand with his wife. He is putting together a punk band in Portugal. He is trying things, not because it is efficient, but because he is trying to figure out what feels like his life. He said he does not want to be a one road guy. When something feels right, he wants to take a shot. We also talked about why storytelling still matters when AI can generate words all day. His point was simple. The missing part is connection. You can generate a story, but you cannot replace the feeling of a real person looking you in the eye and saying something that lands. He ties it back to work, too. In marketing and sales, if you do not know people, you cannot connect to people. Your story falls flat. He is also clear-eyed about aging in tech. He worries about how long he can keep doing what he does, and whether the industry will move on without him. His answer is to stop chasing status. He does not want to manage people. He wants to deliver a specific thing well, mentor when asked, and stay useful. He thinks experience will matter again, not as a title, but as real history you can apply. The part that stuck with me was how he thinks about safety. He does not judge people who stay in the cubicle. He just does not want to end up like his dad, who spent decades in one company and now, at 75, feels like he missed his chance to do more. Marcos wants to look back and say, that was a lot, that was worth it. He framed his goals in a way I liked. He wants to give his kids a few core memories they will actually keep. A trip to Japan for his daughter. A steak in New York for his son, yes, Peter Luger. He wants those things, and he wants to be able to say his own life was good too. He even mentioned he stopped drinking and still enjoys life, which is its own kind of data point. This is the whole point. You do not need a clean plan. You need motion. You try things. You keep what works. You drop what does not. You pay the bills, but you do not let that become the only story your kids learn from you. Marcos is doing it in a way that looks chaotic from the outside, but it has a clear center. He is trying to make sure his life is not just a job history, it is a life. His book is Ana Luz’s Diary, by Marcos Bravo. If you want to see what he made, it is on Amazon. Transcript John Biggs (00:27.042) Welcome back to Keep Going, a podcast about success and failure. I’m John Biggs. Today on the show we have Marcus Bravo. He’s Chilean. He lives in Portugal now. I met him in Poland when we were pros approximately, I think, six years old, I think. That’s what it feels like at this point, right? So welcome, Marcus. You’re an author, you’re a marketer, you’ve done loads of work. Marcos Bravo C. (00:46.072) Yeah, something like that. Yeah. John Biggs (00:55.252) over the years with multiple clients, multiple places, and now you’re kind of doing your own brand. You’re kind of building your own presence. So why don’t you tell me what you’re working on. Marcos Bravo C. (01:03.398) So, well, I like you said, I moved to Portugal from Poland two years already here. And yeah, I needed to start something else. I mean, felt that I was getting old for being the tech guy or the sales guy. And I just thought, well, let’s see what I can do. Right. So a mix of crazy stuff. You try to do everything that you think that you feel that it can. be sort of meaningful to yourself, but you really realize that you don’t know what’s meaningful to yourself. So you have to rediscover all of that. one of the things I’m doing now, I just wrote a book, which was on my bucket list, I guess. I wrote a book. I’m starting with video again. I started putting together a punk rock band here in Portugal. mean, Jesus, I’ve been trying to do everything just to figure out. what’s the right thing to do. And when you have a family, you have to figure out how to the bills. So I’m still having an affair with tech. But basically, I’m just trying to still discover things when I’m 46, which is I don’t know if it’s right or not, but it’s weird. John Biggs (02:06.734) Mm-hmm. John Biggs (02:11.011) What is that impetus to discover as we get older? Marcos Bravo C. (02:16.756) I guess I get so used to, well, I have to figure out how to pay the bills and that’s it. I started figuring out, well, what am I showing my kids? Is it all about money? Is it all about just to go through life without trying to not die of hunger? And I wanted to do something that is meaningful for me as well. I had to sort of ask permission. It’s like, do you mind if I don’t do this? crap, I make less money, but I do something else that might be more meaningful. And that’s what I’m doing. I mean, the whole book came out of almost an accident, just like watching videos of people writing books, trying to come up with an idea. And because I couldn’t write the book that I wanted to write, I ended up writing another book that ended up taking shape. And now it’s on sale. mean, every little step that I’m doing is just sort of showing me something new. And like you said, we’ve been around for a while. We’ve been doing tech. John Biggs (02:48.429) Mm-hmm. Marcos Bravo C. (03:15.374) all the stuff for many years, but there’s always a space for something new, something better, something meaningful. John Biggs (03:25.378) What does it mean to be meaningful, right? So your book is Analyst’s Diary, which is a kid’s book, right? And it’s about a little girl, why don’t you tell us the story? Marcos Bravo C. (03:37.382) So basically, Andalus came out, I was writing a kids book, I was writing a bunch of stories, like very cool, fun, weird, scary, whatever. And then when I was blocked, I was like, well, I need to write something else. And I remember seeing a tweet right before started writing. It says like, with all this happening around the world, we soon we’re to have an Anne Frank in our backyard. And I was like, right, well. What if Anne Frank’s still around? There are many Anne Franks around the world, especially with how things are. So I started to write the story, like, how would I see from maybe like a little bit of a Latin view or like trying to add my own experiences into this little girl called Anna who got stuck in the attic with her brother and her auntie and they’re trying to figure out how to be quiet because noise will bring more people, will bring the bad people. John Biggs (04:06.926) Mm-hmm. John Biggs (04:29.976) Mm-hmm. Marcos Bravo C. (04:30.38) And that ended up taking very nice shape. I started adding all of the things that I knew of storytelling. And I created a story that is maybe not an easy to read story, but it made sense to me and it made sense. mean, my daughter had to approve it. So it made sense to her too. It worked. John Biggs (04:48.782) Is the goal to just do this? Is the goal to allow this to be part of your personality, part of how you grow? Do you think it’s Marcos Bravo’s for the rest of your life? Or is it Marcos Bravo who does everything else that you’ve done before, Marcos Bravo C. (05:11.43) I think it has to be a mix. The first thing I realized for sure is that I don’t want to be the one road guy. But every time or anytime there’s something that feels good, that feels right. The world, let’s give it a shot. For sure I’m writing more. I love writing and I’ve been writing since I was a kid and this is the first time I actually said, and this is because I was unemployed. I’m like, I have all this time in my hand. I need to do something, otherwise I’m gonna go crazy. So I need to put stories in there and it felt right and that’s definitely something I want to keep exploring and we’re going to keep doing. John Biggs (05:52.014) Tell me about storytelling in general. How do you use storytelling in your career? How do you use it to, well, mean, first off, beat AI, right? Because right now we can blast out. We could feasibly blast out your book if we gave it the idea. We would just blast it out. It wouldn’t be any good. But how do you keep that humanity? How do you keep that aspect of storytelling? Marcos Bravo C. (06:09.989) Yeah. Marcos Bravo C. (06:16.271) Well, mean, AI, even though it’s been helpful with many things, I I use it quite often for work, but it was a huge threat for me because I mean, my whole career beside marketing and sense of whatever is because of storytelling is because I found that I can tell stories that people want to listen. And rediscovering that people, yeah, they’re okay with that. can create stories in AI like that. But it’s this connection that is missing, like you and I talking, you and I look at each other and having that feeling, that’s irreplaceable. That’s not going to happen anytime soon. It might happen. Absolutely. mean, anything

    17 min
  8. The Innovators: Inside a Startup on the Cutting Edge of Fintech

    FEB 4

    The Innovators: Inside a Startup on the Cutting Edge of Fintech

    On this episode of The Innovators, I spoke with Jasper Fu, CEO of CoinSub, about what crypto payments actually look like when you strip away the hype and aim for real adoption. CoinSub has been operating for roughly two and a half years and has grown to a 22-person team, most of them engineers. The company’s focus is narrow by design. Instead of trying to convince millions of merchants to adopt crypto directly, CoinSub sells infrastructure to payment service providers. These are the companies that already process card payments for thousands, sometimes hundreds of thousands, of merchants. CoinSub’s bet is that adoption happens faster when crypto looks like just another payment option, not a new system merchants have to learn. Fu framed the problem simply. Crypto and stablecoins are often described as liquid assets, but in practice they are hard to use for everyday payments. Merchants do not want to think about wallets, chains, or conversions. They want money in their bank accounts. CoinSub handles the movement behind the scenes, converting between dollars, Bitcoin, and stablecoins, then packaging that capability so payment processors can offer it under their own brands. For merchants, the experience is meant to feel familiar. Crypto becomes another icon at checkout, alongside cards or digital wallets. Whether funds settle as stablecoins or dollars is not something the merchant has to manage. Fu compared it to card networks. Merchants do not think about how Visa or Mastercard clears transactions, they just expect it to work. That distribution strategy also shapes CoinSub’s view of competition. While many crypto payment companies target merchants directly, CoinSub targets the providers upstream. There are billions of dollars flowing through a relatively small number of payment processors, many of which lack the technical capacity to build crypto infrastructure themselves. CoinSub positions itself as a way for those companies to keep pace without rebuilding their stacks. Usage data suggests there is real demand, even if it remains early. Fu said CoinSub processed roughly $400 million in transaction volume last year. That number varies widely by region and industry, but it reflects actual consumer-to-business payments, not trading or speculation. Some sectors adopt faster than others, including cross-border commerce and industries that struggle to maintain stable card processing relationships. Fu pushed back on the idea that crypto adoption hinges on hype cycles. He views blockchain and tokenization as infrastructure, a more efficient way to store and move data and value. Speculation and scams, he argued, appear in every new technology wave and do not define the underlying system. In his view, hype draws attention, but utility determines what survives. Stablecoins are central to CoinSub’s timing. Fu said regulatory clarity, treasury backing, and growing institutional interest have aligned incentives across governments, issuers, and payment networks. Payments and commerce, he said, are the logical next phase after issuance. Once stablecoins exist at scale, the question becomes how people actually use them. Fu’s path to CoinSub started outside crypto. After leaving a corporate role, he took time off to think about what he wanted to build next. Payments stood out as a place where incremental efficiency could have broad impact. Making money movement cheaper and more accessible, particularly across borders, felt like a net positive use of time and capital. That mindset also shapes CoinSub’s internal culture. Fu said he prefers the startup environment because it allows for empathy-first leadership and long-term thinking. He believes effort cannot be bought, only invited, and that teams perform better when people are treated as contributors rather than interchangeable resources. Looking ahead, CoinSub is expanding beyond its initial engineering phase. The company is working to capture more of the payment service provider market while it still has an early mover advantage. Longer term, Fu sees applications beyond checkout, including payouts, invoicing, and potentially ATMs, anywhere money needs to move across systems or borders. Fu is realistic about maturity. He expects fragmentation before consolidation, with many stablecoins and blockchains competing before a smaller set emerges as dominant. In that environment, CoinSub’s role is to abstract complexity away from customers and let them benefit from whichever systems ultimately win. Crypto payments, in Fu’s telling, are not about replacing everything overnight. They are about quietly fitting into existing workflows until their presence feels unremarkable. That, more than price swings or headlines, is what adoption looks like. Transcript John Biggs (00:07.982) Welcome back to The Innovators, a podcast about amazing people doing amazing things. Today on the show I have Jasper Fu. He’s the CEO of CoinSub, a stable coin operation. We do a lot of crypto on here, so I’m happy to have somebody back from the crypto world. Welcome, Jasper. Jasper Fu (00:27.501) Thanks for having me, John. John Biggs (00:28.588) Yeah. So tell us about CoinSub. How long have you been around and what are you up to? Jasper Fu (00:33.923) Yeah, absolutely. So we’ve been around for two and a half years. The team is about 22 people now with 17 being engineers. And what we jumped into the space to do is like everyone’s heard of this stable coin crypto blockchain Bitcoin stuff, right? And there’s a variety of value, value props. But what we realized is a lot of it’s just not hitting to the mass market. We particularly target payment service providers in fintechs, right? A lot of stable coin around, a lot of Bitcoin around, why can’t we pay with it was our first thought. You say it’s liquid, how do we make it liquid? And as we dug into the space, we realized this early, early stage of adoption, there’s a lot of demand from both the merchants, the businesses, as well as these payment providers to be able to offer this, right? But this is totally new tech to them. And most of the solutions in this space are either going for, hey, directly to the businesses themselves, or they’re these esoteric APIs that are hard for non-technical people to understand. So what we do is we pre-build out the infrastructure so that somebody could go from US dollars to Bitcoin to stable coin to US dollars. And we apply that to different things like payment acceptance and payouts. and we wrap and package that whole thing up and allow other companies, allow other payment providers who are already selling say card payments to now add this additional capability underneath their own brand. John Biggs (02:07.726) Interesting. in a nutshell, is the focus more on stablecoins? Is the focus more on general crypto? What am I as a merchant? So say I’m a merchant, want to sell my widgets online or I want to sell them in the store. What am I doing with you guys? How do you sell to me? Jasper Fu (02:25.924) So merchants usually get their payment products through their payment provider. So that’s the interesting insight that we had, right? You usually only want to work with one person and that might be say your stripe or your clover or whatever it is. So we actually sell to the clovers, you know, the clovers of the world, the payment service, the payment processors of the world. But what that looks like for the merchant is you reach a point of awareness where you’re like, I know that I should probably accept this kind of payment, but at the end of the day, I’m just trying to expand my business and grow my revenue. So for us, it’s just one more thing that gets added on at checkout, and that’s the last thing you have to worry about. Whether it ends up as stable coin or whether it ends up in US dollars in your bank, you shouldn’t have to worry about it. Focus on your business. You don’t worry about how your credit card gets there from Visa or MasterCard, and you don’t worry about how PayPal, Google Pay, Apple Pay, Clarion don’t work. And so that’s the kind of level of adoption we want to bring where people understand that there’s some value there and we just go, great, here you go. Let me make sure that it’s comfortable for you. John Biggs (03:32.383) So the icons when you check out are like credit card, don’t know, PayPal, Venmo, Alipay, and then crypto. OK. You’ve got a lot of competition in that space. How is that working out? Jasper Fu (03:37.997) with crypto. Jasper Fu (03:46.244) So the competition in this space would only apply if the target market is the merchants themselves. There’s very few companies that are actually targeting the payment service providers. If you think about it, there’s hundreds of millions of merchants in the world that capture trillions of dollars of payment volume. But there’s only really thousands of payment service providers, independent sales orgs, and these are the ones that are already kind of selling card processing. they’ve already captured the entire market. And the reality is most of these have been around for 15, 20, 25 years and they’re not tech savvy. So when you get these first movers like a stripe, right, offering stable coin payment acceptance, what that actually does for the rest of the industry is it pressures kind of the middle of the pack or the earlier adopters to take action. And there’s not enough time for them to build it because as you said, the space is saturated and it applies to not just crypto but traditional payments as well. And so the options to buy and to date, we think of ourselves as like orthogonal to the competition. Our difference isn’t in what necessarily we’re offering them as an end product but rather the deployment model. Rather than deploying it to the merchants and trying to onboard millions of merchants, we onboard a couple dozen. payment providers that then grant us access to hundreds of

    20 min
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About

When you're going through Hell, keep going." This is a podcast about failure and how it breeds success. Every week, we will talk to amazing people who have done amazing things yet, at some point, experienced failure. By exploring their experiences, we can learn how to build, succeed, and stay humble. It is hosted by author and former New York Times journalist John Biggs. Our theme music is by Policy, AKA Mark Buchwald. (https://freemusicarchive.org/music/policy/) www.keepgoingpod.com

Information

  • Creator
    John Biggs
  • Years Active
    2022 - 2026
  • Episodes
    154
  • Rating
    Clean
  • Copyright
    © John Biggs
  • Show Website
    Keep Going