Miles Grimshaw

My guests today are Jack Altman and Miles Grimshaw. Jack is the co-founder and CEO of Lattice, an HR software platform. Miles is a General Partner at Benchmark, an early investor and Board Director at Lattice, as well as a former guest on Invest Like the Best. Jack started Lattice in 2015 and has scaled it into a multi-billion-dollar business that already serves over 5,000 organizations. In our discussion, we look at all aspects of building and scaling a software product from both an investor and operator’s perspective, which made this particularly fun to do. Please enjoy my conversation with Jack Altman and Miles Grimshaw. Listen to Founders Podcast For the full show notes, transcript, and links to mentioned content, check out the episode page here. ----- This episode is brought to you by Tegus, the modern research platform for leading investors. Stretch your research budget with flexible expert calls you can trust. At a fraction of the cost of traditional expert networks, Tegus customers pay only what an expert charges – with zero markups and no confusing call credits – netting an average 70% savings. Don’t want to conduct a full hour call? Tegus offers the ability to schedule 30-minutes, an offer you won’t find anywhere else. And they don’t stop there. With white-glove custom sourcing for every project and robust compliance measures, including a dedicated 50+ analyst team that vets every call transcript, Tegus ensures your privacy and protection. As the industry innovator for qualitative insights, Tegus helps you find the right experts you need at a quality and speed that can’t be matched. For a limited time, as a listener, you can trial Tegus for free by visiting tegus.co/patrick. ----- Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.  Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes (00:02:55) - (First question) - How Jack & Miles met at Y Combinator in 2015 (00:04:22) - Lattice found a niche in mid-market HR software (00:07:55) - Discovering Lattice's true market need (00:11:14) - Fear of stalling drove the need for business growth beyond initial product (00:12:06) - Deciding on multi-product focus over up-market expansion (00:17:01) - Prioritizing quality of usage over frequency for customer health scores (00:20:06) - Balancing customer health scores and actual needs (00:24:31) - Prioritized community by spotlighting HR voices (00:28:20) - Building community helps companies sell a vision or lifestyle (00:31:05) - Cultivating broad awareness instead of hard-selling (00:35:33) - Overcoming the culture of 'perfection’ (00:37:22) - Flywheel effect makes suites efficient: lower go-to-market costs, more focus on product (00:41:06) - The challenges of juggling current needs and future demands (00:46:27) - Navigating disagreements and trust-building within a company (00:50:36) - Investors' roles extend beyond founders, focusing on their own goals and interests (00:51:52) - How transparency eases the founder-investor dance (00:55:16) - The changing employer-employee relationship (00:58:37) - Navigating growth from startup to public equity (01:05:43) - Lattice's ultimate aspiration (01:07:42) - Evaluating founders' authenticity (01:11:18) - What Jack & Miles are most embarrassed about, the most proud of, and the most excited for (01:14:30) - The kindest thing anyone has ever done for Jack and Miles

Jack Altman

CEO

LatticeTeespring

Miles Grimshaw

General Partner

Benchmark

Miles Grimshaw is a General Partner @ Benchmark, widely considered one of the best venture capital firms in history. Prior to joining the Benchmark Partnership, Miles was a General Partner @ Thrive Capital where he led investments in Airtable, Monzo, Lattice, Github, Segment, Slack and Benchling to name a few. In Today's Episode with Miles Grimshaw We Discuss: 1. Straight into VC From University: From Yale to Thrive How did Miles come to land a role with Josh Kushner and Thrive right out of Yale? What are 1-2 of his biggest lessons from working with Josh @ Thrive for 8 years? What does Miles know now that he wishes he had known when he started in venture? 2. The Pillars of Venture Capital: Sourcing, Selecting, Servicing: What does Miles believe are the 5 core pillars of successful venture capital? 1-5, what is his strongest and what is his weakest? Does Miles really believe that VCs add value today? What are the most clear ways that Miles have seen VCs destroy value in portfolio companies? 3. Investment Decision Making: From Github to Segment: What is the single most important question that Miles has to answer to say yes to an investment? How does Miles think about both market sizing risk and market timing risk? What have been Miles' biggest hits? What did he learn from making those investments? What have been Miles' biggest misses? What did he learn from missing Figma and Plaid? What have been 1-2 of Miles's biggest lessons so far from working with Bill Gurley and Peter Fenton? 4. AI: What Happens Next: Does Miles believe we are in an AI bubble today? How does he assess the landscape? Why does Miles believe that the "Co-Pilot" strategy is an incumbent strategy? Where does Miles believe the value will accrue; the application layer or the infrastructure layer? What does Miles mean when he says the future is in "selling the work and not the software"? What business model disruption and adoption disruption does Miles believe AI will enable? Why does Miles believe that the analogy of AI to the rise of mobile is wrong?

Miles Grimshaw

General Partner

Benchmark

My guest today is Miles Grimshaw. Miles is in his early thirties and is a General Partner at Benchmark. His experience and success belie his age. He was an early investor in Segment, Benchling, and Airtable, all before they had 30 employees. I have learned a ton from Miles about software investing and that’s why I was excited to have him on the show. We discuss his biological approach to investing, whether pure API companies can be good businesses, and what most has his attention right now. Please enjoy this conversation with Miles Grimshaw.   Listen to Founders podcast   Founders Episode #136 A Success Story: Estee Lauder    Invest Like the Best with David Senra: Passion & Pain   For the full show notes, transcript, and links to mentioned content, check out the episode page here.   -----   This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern Saas platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick.   -----   Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.   Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.   Follow us on Twitter: @patrick_oshag | @JoinColossus   Show Notes [00:02:57] - [First question] - His notion of the investor as a biologist or a physicist [00:05:24] - Why he seeks out new companies with unique business models [00:07:53] - How his investments are based on present and future needs in the market [00:11:55] - Evaluating the genetics of a nascent or small company [00:13:38] - The half-life of information as it flows through a company or platform [00:17:26] - Unpacking how software companies can survive re-evaluation periods [00:21:03] - The power of environment creation and facilitation [00:25:10] - The importance of user conferences [00:25:45] - A company’s potential for a differentiated second act as a sign of good genes [00:30:21] - Product quality, timing, and reinvention in tech startups [00:33:10] - Why it’s crucial for companies to avoid copying their heroes [00:37:41] - Breaking down market perspective on pure API companies [00:41:29] - His views on software targeted to vertical versus horizontal markets [00:44:29] - Carefully leveraging relationships with core customers [00:48:06] - Operational lessons from his experience with the companies he’s invested in [00:50:26] - His maxim that software development is as much an art as a science [00:51:12] - His idea of a product magician in the software industry [00:52:19] - Effects of new products and categories at the forefront of the space [00:58:21] - How software founders should prepare for 2023 [01:01:41] - How both market structure and product shape the genetics of a business [01:04:32] - The challenge of pricing and packaging for SaaS companies [01:06:42] - Cardinal sins in software investing [01:07:42] - The kindest thing anyone has ever done for him

Miles Grimshaw

General Partner

Benchmark