The Tech Trek

In this episode, I sit down withMatt Birnbaum, Partner atPear VC, to discuss one of the most critical aspects of early-stage startups:structuring equity for early hires. We dive deep intohow founders should allocate equity, common pitfalls, and how to ensure flexibility for future growth. If you’re an early-stage founder, considering joining a startup, or just want to better understand the mechanics of equity distribution, this episode is packed with valuable insights.We also discuss Pear VC’sstartup equity calculator, amust-have resource for founders and candidates alike. If you're navigating startup hiring or negotiating an offer, this episode is for you!Key TakeawaysEquity Allocation Matters: The way you structure early equity sets the tone for compensation and expectations in your startup.Early Hires Take More Risk, So They Get More Equity: The first technical hire should receive significantly more equity than the tenth, but many founders don’t account for this.Equity Pools Need Strategic Planning: Many founders either set aside too little or too much, leading to dilution or a lack of hiring flexibility.Plan for a Buffer: Keeping a25% buffer in your option pool allows flexibility for future hires, key recruits, and strategic pivots.Technical vs. Non-Technical Equity: While technical hires often receive a premium, some non-technical roles can be just as critical—founders should plan accordingly.Candidates Should Ask Smart Questions: If you’re negotiating equity, ask about the total equity pool, planned headcount, and how your grant was calculated.Timestamped Highlights[00:00:00]Introduction – Welcoming Matt Birnbaum, Partner at Pear VC, and discussing the episode’s focus on startup equity.[00:01:16]What is Pear VC? – Early-stage investment approach and how Pear supports founders beyond capital.[00:02:37]Why Startup Equity Structure is Critical – How it impacts long-term hiring and company growth.[00:05:22]Common Mistakes in Equity Planning – Founders often rely too much on benchmarks without understanding the logic behind them.[00:07:56]Equity Pool Size & Flexibility – Why 10% is the typical equity pool and the importance of maintaining a buffer.[00:10:44]Negotiating Early Hires’ Equity – How to balance offering enough equity without overcommitting.[00:14:19]How Founders Should Talk About Equity – Advice on explaining equity offers in a way candidates understand.[00:19:35]Technical vs. Non-Technical Hiring – Does a non-technical hire deserve as much equity as an engineer?[00:23:47]The Risk vs. Reward Equation – Why the first hire gets significantly more equity than the tenth hire.[00:27:28]Final Thoughts & Resources – How to reach Matt and access the Pear VC equity calculator.Quote of the Episode"Instead of closing your eyes and picking numbers from a benchmark, take the extra steps to plan your equity spend. It’s the difference between thriving and struggling down the road." –Matt BirnbaumResources & LinksPear VC Startup Equity Calculator: https://pear.vc/how-to-structure-startup-equity-for-early-hires/Matt Birnbaum on LinkedIn: linkedin.com/in/birnbingConnect with UsSubscribe to The Tech Trek for more episodesShare this episode with a founder or candidate who needs to hear it!

In this episode, Amir Bormand speaks withSandeep Bhadra, General Partner at Vertex, about the journey and challenges of early-stage founders. Sandeep dives deep into the psychology of being a founder, the importance of support systems, and how investors can serve as mentors. They also discuss essential skills founders often lack, navigating pivots, and the role of distribution in building a business. If you're a current or aspiring founder—or just curious about the world of startups—this episode is packed with valuable insights!Key Takeaways:The Lonely Road of Founders: Founders often feel isolated as they navigate personal growth and business challenges. A co-founder or coach can make the highs less high and the lows less low.Skills Gaps in Founders: First-time founders often underestimate the importance of distribution and managing teams with diverse skill sets.Pivoting with Purpose: Instead of building endlessly, test new ideas by pre-selling or validating hypotheses before committing resources.The Role of Coaching: Coaching isn't just for founders—investors need to hone their ability to guide without dictating and foster trust with their portfolio companies.Customer-Centric Thinking: Successful founders prioritize understanding customer pain points over the technical capabilities of their product.Timestamped Highlights:[00:01:00] - Introduction to Vertex and Sandeep's role in backing technical founders.[00:02:00] - The psychology of founders: loneliness, personal growth, and the need for mentors.[00:05:00] - Building non-consensus ideas: What makes a startup truly innovative.[00:08:00] - Gaining trust as an investor to help founders open up about challenges.[00:13:00] - Founders’ common blind spots: Distribution and managing cross-functional teams.[00:16:00] - The art of pivoting: How to avoid endless building and validate ideas effectively.[00:19:00] - Amazon’s strategy: Writing the press release first to refine the product vision.[00:21:00] - How to connect with Sandeep: Twitter (X), LinkedIn, and Vertex’s website.Memorable Quote:"The best athletes in the world have coaches, the best musicians have coaches, and founders are no different. Having someone in your corner who can provide perspective makes all the difference." – Sandeep BhadraConnect with Sandeep:Twitter (X):@BhadraSandeepLinkedIn:Sandeep BhadraVertex Ventures Website:vvus.comCall to Action:If you enjoyed this episode,share it with a friend who’s a founder or considering starting their journey. Don’t forget tolike, subscribe, and comment with your thoughts on the episode or topics you'd like to hear more about!

In this episode, Amir Bormand sits down with John Cottongim, Co-Founder and CTO of Roots Automation, to explore how automation and generative AI (GenAI) are revolutionizing the insurance industry. John brings deep expertise from his 13-year tenure at AIG, sharing insights on legacy systems, data challenges, and the evolving role of digital co-workers. He discusses the intersection of process automation, data quality, AI adoption, and how companies can strategically implement AI without disrupting their workflows. Key Takeaways 🔹 Insurance’s Tech Debt is Massive – Large insurance companies operate on hundreds or even thousands of legacy systems, making modernization complex. 🔹 Process Automation is a Game-Changer – Digital co-workers can handle high-volume, structured processes like claims intake and underwriting, improving efficiency without drastic process overhauls. 🔹 The Data Quality Dilemma – Poorly structured, inconsistent data has been a barrier to AI adoption, leading many insurance firms to struggle with leveraging data lakes effectively. 🔹 Choosing What to Automate – The best automation candidates are high-volume, repetitive tasks with clear guidelines. Avoid low-impact projects that don’t drive ROI. 🔹 The Future of AI in Insurance – Instead of a single "super AI," the industry will see a network of narrow AI models trained specifically for underwriting, claims processing, and other specialized tasks. 🔹 Adoption Challenges – Employees are often comfortable with inefficient processes. Successful automation integrates smoothly without demanding drastic workflow changes. Timestamped Highlights ⏳ [00:01:00] – What is Roots Automation? Introducing InsureGPT, digital co-workers designed for insurance automation. ⏳ [00:03:00] – The massive legacy tech burden in insurance: Why do companies still run on decades-old systems? ⏳ [00:06:30] – The data problem in insurance: Why data lakes failed and how AI can improve data capture and structure. ⏳ [00:10:00] – How to pick the right automation projects: Find high-impact, high-volume tasks rather than niche, low-risk ones. ⏳ [00:15:00] – The tech debt of insurance processes: How decades of quick fixes have created a tangled mess of workflows. ⏳ [00:19:00] – Change management and adoption: How to help teams transition from manual work to digital co-workers. ⏳ [00:24:00] – The rise of narrow AI: Why insurance AI models must be specialized rather than all-purpose. ⏳ [00:26:00] – The future of AI in insurance: How companies will need to orchestrate multiple AI models for efficiency. Quote of the Episode "The biggest mistake in automation is choosing a process that’s ‘safe’ but not impactful. If it’s not a high-value problem, no one will care when you solve it." – John Cottongim Connect with John Cottongim 📩 Email: john@rootsautomation.com 🌐 Company Website: Roots Automation Enjoying the Podcast? 💡 Share this episode with a colleague who’s interested in AI and automation in insurance!📩 Subscribe, rate, and leave a review to help us keep delivering great conversations.

In this podcast episode, Amir Bormand interviews Michelle Avery, Group VP of AI at WillowTree, a TELUS International Company. They discuss the process of prototyping Generative AI (Gen AI) solutions and transitioning from prototypes to production-ready applications. Key points include identifying business problems, the importance of intentional prototyping, overcoming data access challenges, and ensuring user acceptance and ROI. Michelle shares insights from her work at WillowTree, emphasizing the role of strategic planning and cross-disciplinary collaboration in successful AI implementation. Highlights 01:34 Prototyping Gen AI Solutions 03:25 Identifying Business Problems for AI Solutions 06:40 Challenges in Prototyping and Data Access 07:55 From Prototype to Production 09:57 Ensuring User Acceptance and Feedback 16:01 Moving Beyond Chatbots Guest: With 17 years of experience across engineering, AI, FinTech, and Robotics, Michelle Avery is a technical leader in the Data and AI space. As the Group Vice President of AI at WillowTree, a Telus International Company, Michelle is passionate about building responsible, production-ready AI applications that address real-world business problems. She leads innovative initiatives in generative AI, oversees impactful research projects, and drives the development of data-intensive applications for Fortune 100 clients. www.linkedin.com/in/michelle-avery-63729bb7 ---- Thank you so much for checking out this episode of The Tech Trek. We would appreciate it if you would take a minute to rate and review us on your favorite podcast player. Want to learn more about us? Head over at https://www.elevano.com Have questions or want to cover specific topics with our future guests? Please message me at https://www.linkedin.com/in/amirbormand (Amir Bormand)

What if the best way for your child to learn wasn’t in a traditional classroom?In this episode, Amir Bormand sits down with Amir Nathoo, Co-Founder and Head of Outschool, a live online learning marketplace that’s rethinking how—and where—kids learn. With over a million learners served, Outschool has quietly become a powerful alternative for families looking to break out of the one-size-fits-all education system.Amir shares the backstory of Outschool’s creation, how the pandemic accelerated online learning, and why education must be rebuilt around engagement, not just content. From the future of AI in personalized learning to working around rigid school systems, this conversation challenges everything you think you know about education.Key Takeaways:Marketplace models can drive systemic change in education—not just convenience.The best teacher for one child might not be the best for another. Fit matters more than credentials.Online learning isn’t a fallback—it can be a powerful first-choice when designed for engagement.AI can support personalization in education, but it can’t replace the human element that sparks true learning.Standardized testing may be holding back students who simply haven’t found the right learning environment.Timestamped Highlights:[01:00] – What Outschool is and why piano lessons over Zoom actually work[04:00] – The “aha” moment: why Amir believed education needed a new system—not just tweaks[07:00] – What happened when Outschool grew 20x in one year during the pandemic[10:00] – Why parents now get online learning—and how that changes everything[14:00] – The hidden tragedy of students thinking they’re “bad at math” because of the wrong fit[21:00] – The two biggest problems in education: personalization and engagement—and how AI fits in[24:00] – Why banning AI is the wrong conversation—and how we should be talking about learning motivation insteadQuote of the Episode:"We created the game. If kids are using AI to jump through hoops, that’s on us—not them. The real problem is they’re not motivated to learn." – Amir NathooResources Mentioned:Outschool – Explore the platform and sign up for freeKhan Academy – Referenced in the discussion of EdTech and learning contentChatGPT / LLMs – Discussed in the context of student use and AI-assisted educationCall to Action:If you're a parent, educator, or just someone who cares about the future of learning—this episode is a must-listen.🎧 Subscribe to the show, share this episode with a friend, and explore the classes at Outschool.com.Let us know what you think learning should look like in 10 years.

In this engaging episode, Amir Bormand sits down with Brian Moseley, Co-Founder and CTO at Sixfold, to explore the nuances of making critical technical decisions. They dive into the concept of technical debt, balancing short-term wins with long-term scalability, and how context plays a crucial role in decision-making. From real-world examples to thought-provoking discussions on collaboration and the evolution of work, this episode offers valuable insights for anyone navigating the challenges of technology leadership.Key Takeaways: Technical Debt Defined: Brian explains technical debt as a trade-off—achieving short-term goals by borrowing from future scalability or efficiency. Context is King: Decisions made without documented context often face harsh judgments in hindsight. Capturing reasoning through comments or specs builds future empathy. Collaboration & Whiteboards: The role of real-time collaboration tools, like whiteboards, is vital in identifying and solving architectural challenges early. The Role of Experience: As teams grow, written documentation and shared knowledge become critical to avoiding pitfalls of tribal knowledge. Remote Work Challenges: The shift to remote work has impacted collaborative decision-making, with teams grappling to replicate the fluidity of in-person brainstorming. Future of Collaboration: Emerging tools, including VR and Gen AI, may bridge the gap for remote teams in technical discussions and knowledge sharing.Timestamped Highlights: [00:01:00] - Introducing Sixfold and its mission to empower insurance underwriters using generative AI. [00:03:00] - What is technical debt? Brian’s analogy of “charging the card” and trade-offs. [00:06:00] - The importance of documenting context to avoid harsh judgment on past decisions. [00:10:00] - Video snippets and asynchronous communication for capturing context. [00:14:00] - Writing, diagramming, and their role in scaling teams effectively. [00:16:00] - The value of whiteboard sessions in identifying potential technical challenges. [00:20:00] - Work-from-home limitations and their impact on collaboration. [00:23:00] - How incorporating collaborative activities can accelerate team productivity. [00:24:00] - Looking ahead: VR and advanced tools as potential game changers for remote collaboration.Memorable Quote:"If you write down your reasoning around the choices you're making and record them, it helps future engineers understand the context. It builds empathy and keeps you from being judged harshly." – Brian MoseleyConnect with Brian: Email: brian@sixfold.ai LinkedIn: Brian MoseleyFollow the Podcast:Don’t forget to like, subscribe, and share this episode! Have thoughts on critical technical decisions? Leave us a comment or connect on social media to continue the conversation.

In this episode, Amir interviews Jen Kodner, a Talent Partner at Threshold Ventures and DFJ Growth, to discuss best practices and challenges in leadership hiring for startups. They explore the importance of finding the right leadership fit for different growth phases, professionalizing key functions, and balancing the hands-on approach required at early stages. Jen shares insights on the dynamics of player-coach roles, setting appropriate expectations for new hires, and the intricacies of delegating responsibilities from founders to new leaders. The conversation provides valuable advice for founders and those involved in talent acquisition at growing startups. Highlights: 02:56 Challenges in Leadership Hiring for Startups 03:54 Professionalizing Functions in Early-Stage Companies 04:45 The Role of Sales Leaders in Startups 06:31 Navigating Founder Expectations and Leadership Roles 17:29 Traits of Successful Leadership Hires Guests: Jen Kodner is the Talent Partner at Threshold Ventures and DFJ Growth, where she advises portfolio companies on strategies to identify, attract, and retain top talent. Before joining these firms in 2018, Jen was a Talent Partner at Box, where she also led recruiting efforts. With extensive experience in talent acquisition, Jen plays a crucial role in helping companies build world-class teams. LinkedIn: https://www.linkedin.com/in/jenkodner/ ----- ---- Thank you so much for checking out this episode of The Tech Trek. We would appreciate it if you would take a minute to rate and review us on your favorite podcast player. Want to learn more about us? Head over at https://www.elevano.com Have questions or want to cover specific topics with our future guests? Please message me at https://www.linkedin.com/in/amirbormand (Amir Bormand)

In this episode, Amir Bormand sits down with Joe Emison, CTO and Co-Founder of Branch Insurance, to discuss how modern software development can be made cheaper, faster, and better. Joe shares insights from his book Serverless is a Game Changer and explains how embracing managed services and serverless architectures can lead to greater efficiency and scalability. He also dives into the cultural and organizational shifts required to truly optimize software development for speed and cost while reducing technical debt.Key Takeaways:✅ Managed Services = Speed & Efficiency – Leveraging third-party managed services allows teams to develop and scale faster while reducing maintenance burdens.✅ Code is a Liability, Not an Asset – The more code you maintain, the more complex your system becomes. Focus only on writing code that directly differentiates your business.✅ Continuing Education is Critical – Software development evolves rapidly, yet many CTOs and engineering leaders fail to keep up with new technologies.✅ Breaking the Myth of IP in Code – Not all in-house software is valuable intellectual property. If a managed service can replace custom code, it often should.✅ The Power of High-Velocity Development – Companies that iterate daily rather than monthly will always outpace their competition.✅ DORA Metrics are Essential – If your team isn’t shipping multiple times a week, you need to rethink your development processes✅ CTOs Must Stay Hands-On or Stay Informed – Leaders who lose touch with modern development practices risk making costly, outdated decisions.Timestamped Highlights:⏱ [00:02:00] – The evolution of software development: How managed services like Twilio have simplified engineering.⏱ [00:05:00] – How Branch Insurance built a full-stack regulated insurance company with 1/30th of the engineering headcount of its competitors.⏱ [00:08:00] – Why software leaders struggle with continuous education and how it leads to outdated development practices⏱ [00:13:00] – The danger of engineering leaders making high-impact decisions without technical awareness.⏱ [00:16:00] – The reality of technical debt and why sometimes rewriting from scratch is the best solution.⏱ [00:21:00] – The biggest mistake companies make: Treating all code as valuable instead of focusing on high-impact differentiators.⏱ [00:26:00] – The Shopify analogy: Why most applications contain large portions of non-differentiated, commodity code⏱ [00:27:00] – Joe’s final thoughts: Optimize for business impact, not code complexity.Quote from the Episode:"The value of a business isn’t the amount of code it writes; it’s the experience it creates and the customers it serves. The less custom code you need, the better." – Joe EmisonResources & Links:📖 Joe’s Book: Serverless is a Game Changer 🔗 Follow Joe Emison: https://www.linkedin.com/in/joemastersemison💡 Enjoyed the episode? Like, subscribe, and share with your network! Leave a comment or review to let us know your thoughts.

In this episode, Amir interviews Rehgan Bleile, Co-Founder and CEO of AlignAI, about her transition from founding a nonprofit organization to leading a for-profit AI company. Rehgan shares insights into the differences between nonprofit and for-profit ventures, the skills required, and the lessons learned. She discusses the origins and mission of Women In Analytics (WIA), a nonprofit aimed at increasing visibility for women and diverse voices in AI and analytics. She details the challenges and strategies involved in scaling both WIA and AlignAI. Rehgan also talks about her passion for entrepreneurship, the importance of intentionality in business, and the evolving role of data science. The episode offers valuable takeaways for aspiring nonprofit founders and startup entrepreneurs. Highlights 01:40 Women In Analytics: Mission and Recent Conference 03:25 Challenges and Growth of Women In Analytics 10:43 Transitioning to AlignAI: Motivation and Journey 16:38 Skills and Lessons from Nonprofit to For-Profit 19:07 Intentionality and Unique Positioning in Business Guest: Rehgan Avon is the Co-Founder and CEO of AlignAI, a company focused on developing tools and strategies to help organizations effectively implement AI and data-driven initiatives. With a background in industrial engineering and a passion for advancing AI education, Rehgan has a strong track record in the tech industry, including founding Women in Analytics, a nonprofit dedicated to increasing visibility and opportunities for women in data science and AI. She is a recognized leader in AI, analytics, and education. https://www.linkedin.com/in/rehganavon/ https://www.womeninanalytics.com/ ---- Thank you so much for checking out this episode of The Tech Trek. We would appreciate it if you would take a minute to rate and review us on your favorite podcast player. Want to learn more about us? Head over at https://www.elevano.com Have questions or want to cover specific topics with our future guests? Please message me at https://www.linkedin.com/in/amirbormand (Amir Bormand)

In this episode, Amir sits down with Eli Wachs, Co-Founder and CEO of Footprint, to dive into the real-world challenges of building a startup with long-term intent. From resisting the hype of building fast to making strategic bets with limited data, Eli breaks down how he and his co-founder crafted a one-year roadmap, how they reassessed it, and how they make calls about what comes next. If you're a founder, product leader, or builder navigating roadmap trade-offs, this one’s for you.🧠 Key Takeaways:Founding with purpose > founding for hype: Eli challenges the "build fast" startup mentality and advocates for building when the problem is truly worth solving.One-year clarity: Footprint launched with a tightly scoped one-year plan that drove team formation and product focus.Betting on the unknown: Not every decision is backed by data—some are smart bets that may take months (or years) to pay off.Choosing the right customers: Not every early user is a good design partner. Pick customers that will co-build with you, not just use your product.Diverging co-founder visions can be an asset: Differing long-term views, when managed well, can surface better strategic outcomes.💬 Quote:"Entrepreneurs don’t have diversified portfolios. So if you're starting a company, you better be damn sure the problem is worth a decade of your life."⏱️ Timestamped Highlights:[00:01:00] Footprint explained: “Stripe for identity”—a modern take on KYC and secure onboarding.[00:03:00] Why Eli pushed back on the “smart people should start companies” narrative.[00:05:00] Launching with a clear one-year product roadmap—and why it mattered.[00:07:00] Building around the founding team’s strengths and sequencing product development accordingly.[00:09:00] The two big product bets they made—and how one took a year to pay off.[00:13:00] The emotional and mental weight of making roadmap decisions under uncertainty.[00:15:00] Why early customers should be intentional picks, not just any logo.[00:17:00] Finding signal for long-term product ideas through prospect conversations.[00:20:00] Whiteboard moment: when a co-founder’s product pitch finally clicked and redirected priorities.[00:22:00] How to evaluate what you're uniquely positioned to build (and what to leave alone).[00:23:00] Eli's contact info and his open-door policy for helping other builders.🔗 Connect with Eli:🐦 X: @EliWachs💼 LinkedIn: https://www.linkedin.com/in/eliwachs/