Ventures

In this episode of Ventures, my guests Kim Porter (https://hatchone.com), Eric Sullivan (https://thumos.io/), Sol Cates (https://www.linkedin.com/in/sol-cates-649736/) and I go “meta” and ask questions about questions. We discuss creatively in career paths, finding purpose, doing good, helping humans flourish, proving middle-schoolers with mentorship and encouragement, pursuing interesting professional questions, and connecting people. Visit https://satchel.works/@wclittle/ventures-episode-39 for detailed notes and links to resources (videos, articles, etc…) mentioned. You can watch this episode via video here. In this episode we cover the following:     1:27 - Sol tee-up and introduction of Kim and Eric2:54 - Kim introduction 4:52 - Eric introduction8:24 - Sol introduction 10:53 - Creativity of the career path. What is your advice for college students today or those who are reinventing themselves right now? (Kim first) 16:38 - Eric’s thoughts on the above question. 23:30 - Recap on advice for life, Dharma, calling, purpose, what wakes you up… Sol’s thoughts on the above question.29:40 - Purpose of life is to find your purpose. For Kim, where is she in this journey and what questions are coming to mind that she is pursuing? 32:40 - Clarity on doing good. Eric’s thoughts on the above question. 37:32 - Building on the foundation of purpose and personal questions, what professional questions are driving you?  (Starting with Kim’s thoughts)38:51 - Sol’s thoughts on the above question. 42:30 - Eric’s thoughts on the above question (“Am I asking the right questions” // “Do I have the right exposure I need in order to correlate the right data points in order to ask the right questions”?)46:15 - The way to “tool up” getting exposure to the right things to ask the right questions.49:32 - Origin of the “flywheel”. For Kim, she had someone who noticed her earlier in life. Human Flourishing. Question: how do we solve the problem of helping more people get noticed and have mentorship from other humans? (Sol’s thoughts re: an app) 54:14 - Kim’s thoughts on the above question. 56:52 - Eric’s thoughts on the above question. 58:35 - Creating the room to bring the right team around a person to notice them. “You can create leaders”. 1:00:13 - Sol’s special superpower to bring people together. He’s a super-connector. One of the most valuable superpowers in the history of the world.1:01:10 - Final thoughts from the group. Reflections and questions for the future. (Kim’s thoughts regarding gratitude)1:02:37 - Eric’s thoughts on the above. Optimism that human flourishing is possible. Advice for a young person: you can create your own reality. Don’t settle for what the world tells you to do. 1:03:55 - Sol’s advice: pay it forward. Be a good samaritan. Find a way to help others. 1:04:57 - Where can people find Kim (https://hatchone.com) // Eric (https://thumos.io/) // Sol Cates (https://www.linkedin.com/in/sol-cates-649736/) 

In this episode of Ventures, my guest Jenna Langer (https://www.linkedin.com/in/langerjenna/) and I discuss the nuances of product and growth from the perspective of an early stage startup (Livefyre) all the way through acquisition by Adobe. We talk about Jenna’s entrepreneurial story, wearing many hats, team composition strategies, the skill stack of a product manager, professional life in an enterprise, and lessons for startup founders. Visit https://satchel.works/@wclittle/ventures-episode-38 for detailed notes and links to resources (videos, articles, etc…) mentioned. You can watch this episode via video here. In this episode we cover the following:  1:10 - Jenna intro, journey from preparing for work with startups, through building a startup, through being acquired by Adobe, to now working again with startups.5:59 - What was Jenna up to personally and professionally that prepared her for startups?12:08 - Intuition around “why Livefyre” ?.. Why did Jenna choose to invest her time into the new startup? 15:40 - Wearing many hats. What was Jenna’s story of the hats she wore to help the company grow in the early stages?18:51 - From an education standpoint, how does Jenna think about “product” vs. “design” vs. “product management”? 22:00 - re: Startup Rocket (appreciate the shout-out). The importance of learning from others. Team composition design and nuances. Where does Jenna see common holes in early stage startup teams? 26:44 - What did the support structure around the core team of Jenna’s startup look like? (investors, advisors, supportive customers, etc…)28:36 - Thinking you are good at product and then realizing you aren’t. How do you “teach product”? 33:10 - The skill stack for a product manager. Worth re-listening to the previous section. How does Jenna think about the “growth” part of the product/growth dance? 38:09 - The concept of a “local maxima” - what if we are climbing the wrong hill? How does Jenna think about the dangers of climbing the wrong hill regarding product vision?42:37 - The desire to “pause” and identity and solve problems. The pitfalls of running too fast that break things. 45:05 - Discussion about Jenna’s work in Adobe. What was attractive to Adobe about Livefyre? 47:56 - Was the transition into enterprise life like for Jenna after the acquisition?51:21 - Holistically, from the frame of going from startups to enterprises, what are the things to learn? What can startups learn after going into enterprises after an acquisition? 55:27 - Learning from Jenna’s holistic story. What’s next for Jenna? 59:53 - Where can people find Jenna online? https://www.linkedin.com/in/langerjenna/ //  http://www.jennalanger.com/ 

In this episode of Ventures, my guests Kelly Jo Horton (https://www.linkedin.com/in/kellyjohorton/), Sol Cates (https://www.linkedin.com/in/sol-cates-649736/) and I discuss marketing operations from a startup and enterprise perspective. We dive into Kelly Jo’s story entering the space, the need for a marketing operations expert as early as possible in a startup, how to avoid technical debt with your MarTech stack, why to setup a centralized command center, and how/why to retool a broken MarTech data infrastructure.Visit https://satchel.works/@wclittle/ventures-episode-37 for detailed notes and links to resources (videos, articles, etc…) mentioned. You can watch this episode via video here. In this episode we cover the following:  1:47 - Sol tee-up and introduction of Kelly Jo2:58 - Kelly Jo personal intro, background, brief career story, tech history, and overview of marketing operations.8:04 - What was the career path that Kelly Jo thought she was going on in the early days and how/why it pivoted.14:47 - Where did in Kelly Jo’s career did she turn toward data and marketing operations?17:48 - In the hypothetical example of a 3-person team (technical, business, and creative), how should they think about setting themselves up for success to learn from their data.20:32 - Until the archetypal founder team has the money to hire a senior marketing operations expert, what should be the foundational work that the team should do in order to not rack up too much technical debt with their data.23:01 - Does Kelly Jo have a recommended MarTech stack for early stage founders?26:44 - Valuing a marketing operations expert. More discussion about an ideal stack from an enterprise angle for B2B work. 35:15 - Comments about the quantity of strong female leaders in marketing operations. 35:43 - From an enterprise angle, what are the common problems that Sol sees on the marketing operations side of things? 37:40 - The importance of having a centralized command center, at least the admin functions. 41:02 - Identifying yet another hole in startup capabilities (tech/marketing). 42:55 - Customers buy business outcomes43:38 - Resetting the marketing operations team/stack, what is Kelly Jo’s experience of retooling a marketing operations team and associated software tooling? 46:02 - Yet another “type of CMO to hire” in startup land.46:33 - Where can people find Kelly Jo and Sol online? https://www.linkedin.com/in/kellyjohorton/, https://www.mopspros.com/mopstalks, https://www.linkedin.com/in/sol-cates-649736/  

In this episode of Ventures, my guests Steve Crepeau (https://www.truesalesresults.com/), Sol Cates (https://www.linkedin.com/in/sol-cates-649736/), and I discuss the nuances of sales, including characteristics, values, tactics, and techniques for helping people progress along the buyer’s journey. Our discussion expands from complex B2B sales to how the “inflection point” concept can be applied to other areas of startups and enterprise sales, including “selling” your team and investors on your idea as a startup founder.  Visit https://satchel.works/@wclittle/ventures-episode-36 for detailed notes and links to resources (videos, articles, etc…) mentioned. You can watch this episode via video here. In this episode we cover the following:  1:01 - Sol tee-up and introduction of Steve2:40 - Steve introduction, background, and story of True Sales Results.5:23 - Sol’s reflections of meeting Steve and learning about sales leadership.6:35 - Did Steve always have the personality of a salesperson even in his childhood? 9:10 - Backing up, what is sales? What kind of characteristics do you need to be good at sales?15:27 - Business to Business (B2B) buyers are interested primarily in purchasing business outcomes. (Sol talking about his past as a Sales Engineer). 17:36 - Deep dive discovery and discernment process as part of True Sales Results services, including talking to customers of customers.21:30 - For a growing startup, from an education perspective, how do you build and scale a sales team?27:17 - Not as simple as having someone in your network shadow you...it requires building story narratives and the types of things that True Sales Results provides for their clients. (hint: not “rolodex selling”)32:55 - Sol reflecting on early bootcamps with Steve, learning functional sales techniques, including understanding “the inflection point” during the buyer’s journey. 35:42 - Steve reflecting on Sol’s video testimonial in a busy conference hall36:24 - During the discovery process with Steve’s customer’s customers, Steve uncovers the emotion during the decision making process. The emotional impact. Sales people are good at making people feel very uncomfortable. Example question to ask: “What is the cost of doing nothing” ? 38:00 - More discussion around “the inflection point”. 40:40 - Making a buyer “troubled” to get to the inflection point. Examples from cybersecurity. 42:37 - Sol recalling a story that Steve shared in the past around buying a car...about a customer coming to the inflection point.45:40 - Other examples outside of Cybersecurity. (e.g. AI/Medtech). The inflection point is literally life or death for some buyers (such as hospitals). 55:02 - Remapping sales stages. Thinking you know why your customers buy your stuff (and being wrong).57:01 - What can founders learn from the insights from this episode regarding “selling” their team, investors, partners, etc… (including themselves). 59:31 - Avoid random acts of selling. Focus. Lessons learned. Sol recommends focusing on the problem, understanding it from multiple angles...and then, understanding if it’s valuable to make the problem go away…..then innovate. 1:01:29 - The best way to convince a team and investors to join you is to focus on the business outcomes of your customers.1:02:08 - Where can we find Steve and Sol online? www.truesalesresults.com & https://www.linkedin.com/in/sol-cates-649736/

In this episode of Ventures, designer/developer Perry Azevedo (https://www.linkedin.com/in/perryazevedo/) and I discuss the importance of a co-founder team having product and design capabilities, the important nuances between “product” and “design”, examples from products that Perry and I have built together, and the future of UX design in the era of low-code/no-code applications. Visit https://satchel.works/@wclittle/ventures-episode-35 for detailed notes and links to resources (videos, articles, etc…) mentioned. You can watch this episode via video here. In this episode we cover the following:  1:43 - Perry introduction. From “Webmaster” to designer/developer over the last few decades.10:31 - Going back to when Perry was first in his government job, from an education standpoint, what was “design” and “tooling” for the web back then in the late 90s?14:30 - How did Perry’s understanding and development of the design/development craft from Perry’s experience in formal education? 18:56 - In startup land, there is typically a business person, a technical person, and ideally a product/design person -- i.e. a Hustler, Hacker, and Hipster. What is Perry’s advice for Business/Technical founders looking for Product/Design help? 24:04 - What should the business and technical person be aware of when picking a co-founder - and if they had to lean one way or another, which way should they lean? 26:53 - A word of caution to business/technical people out there (hint: you probably aren’t very good product people). 30:40 - Walking through product examples and the Design/Product: VendorHawk https://www.geekwire.com/2018/servicenow-snaps-vendorhawk-help-customers-manage-saas-spending/ 35:35 - Another example of a product that Perry and Will built: https://www.startuprocket.com/ 39:50 - The story behind the hexagon logo for Startup Rocket - and the story behind logos in general.41:22 - More about the history and founding story of Startup Rocket41:56 - What is the next stage of learning for Perry as a world-class designer? (No-code/low-code; we may not need to write code anymore soon)45:41 - Going from design to coding up a product - are there any downsides to this personally for Perry?48:51 - The “T” analogy for people; how founders should identify people to fill out their team.49:50 - Where can people find Perry online? @perryazevedo on the socials, or go directly to https://www.protaventures.com 

In this episode of Ventures, my guests Susie Kataoka (https://www.linkedin.com/in/susiekataoka/), Norris Liu (https://www.linkedin.com/in/thenorrisliu/), and I discuss the origin story of Zebra Health, the work they are doing to bring transparency to the Personal Protective Equipment (PPE) global market, starting a joint venture between their startups, distributing rapid antigen and antibody tests for COVID-19, and aspiring toward blockchain/Web 3.0 opportunities for any marketplace that involves brokering trust. Visit https://satchel.works/@wclittle/ventures-episode-34 for detailed notes and links to resources (videos, articles, etc…) mentioned. You can watch this episode via video here. In this episode we cover the following:  1:45 - Susie introduction and background, Transpara to Zebra Health3:00 - Norris introduction and background, EHLP to Zebra Health, describing the origin of the name “Zebra Health”7:43 - for Susie and Norris, was being entrepreneurial something they did as kids or was it something they picked up later in life?10:00 - What was the process like of starting a formal Joint Venture? At what point did Susie and Norris know that was a good idea?13:59 - Regarding trust, communication, and transparency (or lack thereof); what is going on in the Personal Protective Equipment (PPE) marketplace globally? (A discussion about the fraud and scams going on in the industry)18:35 - More discussion about the “good” and “bad” side of the global PPE market. 27:13 - What products and services does Zebra Health offer? 29:30 - What is the vision/mission of Zebra Health today? 31:03 - What is the difference between a COVID-19 antigen test and antibody test? (FYI, Zebra Health is a distributor of these tests - visit https://zebra.health to learn more)39:04 - Does having COVID-19 make someone immune from getting it in the future?41:23 - Who is Zebra Health for?  (Geared toward health care professionals, health care organizations, and governments)41:59 - Would manufacturers of PPE/tests and distributors be partners with Zebra Health? 43:27 - What needs to change in the USA and the global system regarding PPE distribution? (Setting standards, transparency, and open markets) 46:57 - Web 3.0 / Blockchain considerations for brokering trust / supply chain management, even outside the PPE world (e.g. in commodities trading).55:26 - Call to action for Web 3.0 developers to help build a decentralized application for brokering trust. 55:39 - How can people best find Susie/Norris and learn more about Zebra Health? Go to https://zebra.health and feel free to contact susie@zebra.health and norris@zebra.health56:25 - Zebra Health is more than just PPE. They are distributing test kits (antibody and antigen) and equipment such as air filtration systems and sanitation stickers).57:39 - Results from testing internally. We tested 13 members of our team, check out https://zebra.health/blogs/news/thirteen-members-of-our-team-were-given-covid-19-rapid-antibody-tests-here-s-what-we-learned   

In this episode of Ventures, my guests Bill Murphy (https://www.linkedin.com/in/williamwmurphy/), Sol Cates (https://www.linkedin.com/in/sol-cates-649736/), and I discuss the worlds of private equity and investment banking, how founders should think about engaging strategic investors, the different stages of technology leadership as a company grows, and the services that Cresting Wave (https://www.crestingwave.com/) offers to help tech companies mature operations and execute go-to-market strategies. Visit https://satchel.works/@wclittle/ventures-episode-33 for detailed notes and links to resources (videos, articles, etc…) mentioned. You can watch this episode via video here. In this episode we cover the following:  1:35 - Sol tee up and intro of Bill3:03 - Bill introduction, initial stories from being part of the founding teaming of CapitalIQ, CTO of Blackstone, and Managing Partner at Cresting Wave. 10:15 - From an education standpoint, what is investment banking? Why should people care about it? 12:04 - What is private equity (PE)? At what point should founders think about having meetings with PE folks?16:11 - Interacting with PEs/VCs that can bring real value-add, i.e. those that want to go on that journey with you. 19:14 - Getting the early company engine started - first customer and first loss. 20:30 - The balance of having a “north star” versus pivoting.21:22 - Brief background of Sol and how his journey interacts with these topics.25:30 - Customer segments/targets: broad vs. specialized. 30:12 - Stages of technology leadership: beginning phase to that first transition into management/delegation?33:51 - Where can Cresting Wave help as technology founders grow their companies? (the go-to-market side).36:47 - Creating a good culture when company building37:35 - Personality diversity / personality tests40:15 - The next horizon in the growth of a technology leader, after the delegation mode has been in place for a while.   42:18 - Communication and processes, openness and transparency. 44:00 - Commentary on waterfall design vs. agile. 45:13 - More about Cresting Wave. Who is the ideal customer? (Free services and ideas to tech leaders curious about optimizing their game, and go-to-market services for technology companies...helping the first handful of conversations with potential clients)48:48 - Where can people follow up and learn more? https://www.crestingwave.com/ // https://www.linkedin.com/in/sol-cates-649736/ 

In this week’s episode of Ventures, my guests Tony Rutkowski (http://www.circleid.com/members/6809/), Sol Cates (https://www.linkedin.com/in/sol-cates-649736/), Tony Sager (https://www.cisecurity.org/) and I extend last week’s conversation about cybersecurity and web 3.0. We dive into topics related to international data controls, entrepreneurship in a global landscape, 5G, SSL certificates, and the evolving definition of trust. Visit https://satchel.works/@wclittle/ventures-episode-32 for detailed notes and links to resources (videos, articles, etc…) mentioned. You can watch this episode via video here. In this episode we cover the following:  1:31 - Sol briefly recapping last week’s episode2:17 - Tony S. introduction of Tony R. 3:33 - Tony R.’s introduction, 50+ year history in cyber and cybersecurity, from a radio amatuer to launching Saturn 5s, to federal service, to his work in telecommunications and security, to 5G. 20:43 - Recap of the questions from last week regarding lessons for Web 3.021:32 - Longer recap from Sol through Web 1.0, 2.0, and 3.0 conversations from last week.22:42 - Tony S: “This is not the first round of utopian thinking”. The struggle of moving to cloud and the body of enforcement. He grew up in a world where trust was a binary decision. Today’s world of trust is a much more nuanced “negotiating” decision.28:47 - Tony R’s commentary on FCC attempts to implement international reporting mechanisms of problems. (Also commentary on antitrust efforts and 5G)34:59 - Creating trust and encouraging anti-corruption in cyber35:46 - Cloud computing, fog computing, and edge computing: implications of 5G38:25 - Question for TonyR - what should bright-eyes entrepreneurs be aware of in terms of problems/potholes with international cybersecurity. 40:41 - Advice for entrepreneurs: everybody has an idea, but not everyone understands the context they are selling into. 42:15 - Commentary on Alibaba, Google, Elon Musk, and AWS. Matching users/funders with people who know how to code.44:28 - Commentary and education on extraterritoriality49:43 - Sovereignty and Data51:20 - CA/Browser forum53:48 - Let’s encrypt - what happened there and why is it problematic? Rational decisions individually versus systemic risk (e.g. Solar Winds). http://www.circleid.com/posts/20200209_truth_in_web_digital_identity/ http://www.circleid.com/posts/20190124_creating_tls_the_pioneering_role_of_ruth_nelson/1:02:28 - Are SSL certificates as simple as ensuring the data from point A to point B is encrypted? (No, they also should signal trust and verification of the provider)1:06:43 - The slight of hand and scaling of trust1:07:30 - The importance of an international perspective, especially amongst USA-based entrepreneurs. 1:08:40 - Where can we find Sol, Tony S, and Tony T online. https://www.linkedin.com/in/sol-cates-649736/, https://www.cisecurity.org/, http://www.circleid.com/members/6809/ 

In this episode of Ventures, my guests Tony Sager (https://www.cisecurity.org/), Sol Cates (https://twitter.com/solcates), and I discuss Tony’s journey through the National Security Agency during the cold war and dawn of the Internet. We talk about how Sol and Tony crossed paths, and how cybersecurity has evolved over the past 50 years, and how the Web 3.0 generation can (and should) learn from the Web 1.0 generation. Visit https://satchel.works/@wclittle/ventures-episode-31 for detailed notes and links to resources (videos, articles, etc…) mentioned. You can watch this episode via video here. In this episode we cover the following:  2:07 - Sol introduction of Tony2:41 - Tony intro, & background, including a history lesson of the Internet and his work with the NSA.8:53 - Sol background and intro for him and how his story intersects with Tony’s. 13:22 - A different mindset; “offense” and “defense” in cybersecurity.15:13 - Independence Day vs. Groundhog Day in cyber defense.  (it’s more like Groundhog Day) 16:50 - Reformed Government Monopolist19:00 - Public service in the DNA of the decision makers in the NSA21:17 - Tony’s story where his boss was the mainstay of the math program. “When we put this stuff out there…. Suppose somebody finds a mistake in it? What are we going to do?” 25:09 - Parallel in the outside world where entrepreneurs want to “do go” as well. “Crypto vs. OG Crypto”. More here about Will’s story. 30:19 - Education on cyber and security on the Internet.  Why is cybersecurity 101 more like “Groundhog Day” vs. “Independence Day”? 34:47 - Common Command and Control: Never go to war without your friends, you never know who your friends are until right before war, and many of your friends can’t stand each other. 37:45 - Why the internet was originally designed.  Remembering the cold ware. Web 1.0, 2.0, and 3.0. Are the Web 3.0 folks on to something real? 44:43 - Self-sovereign identity and security. How do we weed out the negative part of the system? 51:01 - Analogy of teeth getting pulled by barbers back in the day when there weren't dentists. It takes awhile to codify the knowledge and build the mechanisms around particular areas (like the Internet).  52:53 - Where can people find Tony and Sol online? Cisecurity.org & sagercyber.org // and @solcates on Twitter.   Special thanks to our sponsor: https://www.startuprocket.com

In this episode of Ventures, my guest Cheryl Kemp (founder of https://indifit.co/) and I discuss her journey of starting a company at the beginning of the pandemic, finding co-founders, leveraging no-code technology to validate her idea, pivoting into a completely different business model, providing software for fitness instructors, experimenting with growth strategies, and raising money in 2021. Visit https://satchel.works/@wclittle/ventures-episode-30 for detailed notes and links to resources (videos, articles, etc…) mentioned. You can watch this episode via video here. In this episode we cover the following:  1:45 - Cheryl quick intro, background, and high-level description of Indifit.3:16 - Did Cheryl have the entrepreneurial drive as a kid or did it come later in life? 5:31 - Will’s story of selling pictures of aircraft carriers as a kid.  6:06 - What kind of work did Cheryl do earlier in her career? 8:03 - Appreciation for entrepreneurs that start restaurants & cafes. 9:02 - Where did the idea of Indifit come from? (Cheryl mentioned this program: https://techcrunch.com/2020/04/28/cleo-capitals-sarah-kunst-launches-a-fellowship-for-laid-off-workers/) 16:22 - Was the program ongoing or a one-time thing? 16:50 - How did Cheryl go through the process of building and validating the idea?19:14 - Discussion about the Indifit business model22:00 - A discussion about the no-code/low-code movement. e.g. https://www.sharetribe.com/ 24:08 - How is indifit going? How are Cheryl and her team doing? 28:20 - How are Cheryl and her team building trust/culture remotely? 31:57 - Was there an “aha” moment with regard to Indifit’s pivot to sell software for instructors rather than be a marketplace? 36:19 - Did Indifit’s no-code approach help with their pivot? How did she surface the data to know when to pivot? 38:29 - How is Cheryl thinking about their growth strategy from here?43:05 - Fundraising conversation. What has the process been like to court investors? 47:54 - Commentary about the VC industry in general and strategically finding the right investors.57:22 - What is the best way to follow Cheryl and Indifit online? (Go to https://cheryl-kemp.com and https://indifit.co/ ) Special thanks to our sponsor: https://www.startuprocket.com