Alex MacCaw is the founder of Clearbit and Reflect, and his journey with each company has been wildly different. Clearbit took more of a “classic” startup approach—raising VC money, hiring hundreds of people, and working from an office in SF. In 2020, he charted a new course by replacing himself as CEO at Clearbit, selling all his possessions and living full-time on a sailboat in the Atlantic. And now he’s building his new company Reflect in with a totally different approach —building a fully remote & asynchronous “lifestyle” company that decidedly eschews VC money and the other common hallmarks of a tech startup. Alex shares everything he’s learned as a founder and why he believes building startups should not be one-size-fits-all. Blake and Alex talk through: (7:07) Pros/Cons of being asynchronous by design(09:01) Why Alex doesn’t believe in remote work for large companies(10:11) Remote work pitfalls(14:21) When to replace yourself as CEO(15:52) How to find your zone of genius(18:31) When do startups hire a CFO or COO?(21:14) #1 piece of advice for founders(24:14) Things to know before you found a startup (B2B vs. B2C)(27:27) Why not raise venture capital(28:28) When startups should (or shouldn’t) raise venture capital(29:40) How Reflect started crowdfunding(39:14) What AI and ChatGPT is good for(44:13) Best time to start a company(46:20) Not all startups need VC funding(47:16) Advice for VCs from a founder

Patrick says work-life balance is the wrong framework. It’s more about work-life fit and finding what suits you best. This is especially true for startup founders, where your work is often all-consuming.Episode Highlights[00:32 - 02:30] Thoughts on work/life balanceMentioned in this episode:Sign up for OpenView's weekly newsletterConnect with Patrick on LinkedInFollow Patrick on TwitterSubscribe to Blake Bartlett on YouTube.Podcast produced by OpenView.View our blog for more context/inspiration.OpenView on LinkedinOpenView on TwitterOpenView on InstagramOpenView on Facebook

Culture at a startup is always tricky, but there’s one common mistake founders should avoid at all costs. It’s the desire to make everyone happy all the time. Patrick says this leads to a “culture of accommodation” which ultimately ends up not working for anyone. Hear Patrick’s journey as a founder to define the culture at ProfitWell, and how you can do the same at your startup.Episode Highlights[00:03 - 01:31] Episode intro: Patrick Campbell[01:59 - 04:04] What is the role and importance of company culture in today's market environment?[06:39 - 10:26] The culture of ProfitWell and the journey to get there[12:15 - 16:26] The most charitable interpretation[17:23 - 20:08] ProfitWell values and four principles[20:21 - 23:16] Speaking their mind, being human in the most charitable way[21:11 - 23:16] Values and principles must have trade-offs[23:16 - 25:41] Here's how we operate, transparency in hiring[25:46 - 32:10] Advice for making culture something more than theoretical, a real experienceMentioned in this episode:Sign up for OpenView's weekly newsletterConnect with Patrick on LinkedInFollow Patrick on TwitterSubscribe to Blake Bartlett on YouTube.Podcast produced by OpenView.View our blog for more context/inspiration.OpenView on LinkedinOpenView on TwitterOpenView on InstagramOpenView on Facebook

Every startup wants to create a category. This is often a mistake. Or at least it’s prioritized too early by many founders and marketers. Ryan Carlson, longtime CMO at Okta, explains why this falls flat with customers and what to do instead.Key Takeaways: [00:31 - 01:53]  A noted skeptic on category creation[01:54 - 02:15] Everybody wants to be a category creator[02:16 - 03:19] Focus on how they're better than the alternativeMentioned in this episode:Sign up for OpenView's weekly newsletterRyan Carlson, Chief Marketing and Strategy Officer at WizLinkedInTwitterSubscribe to Blake Bartlett on YouTube.Podcast produced by OpenView.View our blog for more context/inspiration.OpenView on LinkedinOpenView on TwitterOpenView on InstagramOpenView on Facebook

Okta’s CMO for 5+ years, Ryan Carlson, says marketing’s guiding light should be the company mission and values. Marketing’s job is to tell the story of the company, not to merely promote the product or drive leads into the top of a funnel. Authentic marketing is rooted in the BIG questions. Why does this company exist? Who should care about that and why?Today’s episode will help you:Understand this strategic approach to marketingSee the impact strategic marketing has on your audienceHow to hire mission/values-aligned marketersLeverage Ryan’s playbook for company storytelling by working directly with customersKey Takeaways: [00:19 - 03:37] Introduction to Ryan Carlson, and thoughts on company culture in the world of marketing[03:44 - 06:53] What should define culture is the mission, values, and vision[06:54 - 10:00] Imparting importance, and showing why culture mattered at Okta[10:02 - 13:32] Authenticity, avoiding hyperbole and marketing BS[13:43 - 16:10] Who do you hire to marketing leadership to operate more authentically?[16:13 - 18:18] Hiring true believers, and avoiding a "customer's wrong" mentality with product market fit[19:26 - 22:45] Understanding why people like the product and the people behind it[22:48 - 25:40] Combining pen to paper with mission, values, and vision[25:42 - 28:27] Storytelling and presentations, how they impact retention[28:30 - 32:26] Story and history of your company is different[32:32 - 35:37] Figuring out if a company operates by its values as a candidateMentioned in this episode:Sign up for OpenView's weekly newsletterRyan Carlson, Chief Marketing and Strategy Officer at WizLinkedInTwitterSubscribe to Blake Bartlett on YouTube.Podcast produced by OpenView.View our blog for more context/inspiration.OpenView on LinkedinOpenView on TwitterOpenView on InstagramOpenView on Facebook

Raj says that most of the PLG advice out there today is missing a key foundational point: data. Many PLG companies still rely on traditional sales & marketing software that keeps data in silos. The key to winning in PLG starts with your data infrastructure, and wiring it up early helps you scale later.Mentioned in this episode:Sign up for OpenView's weekly newsletterRaj Sarkar, CMO & AdvisorLinkedInTwitterSubscribe to Blake Bartlett on YouTube.Podcast produced by OpenView.View our blog for more context/inspiration.OpenView on LinkedinOpenView on TwitterOpenView on InstagramOpenView on Facebook

B2B marketers usually overlook brand in their marketing mix. Brand marketing is only for CPG companies, right? Raj makes the case that brand marketing is not optional, if you want to win your category.But brand marketing isn’t just buying a Super Bowl ad. Before you think about channels, you need to define your brand identity and build awareness. Done right, brand marketing can become an infinitely scalable strategy to drive growth.Key Takeaways: [01:19 - 04:05] What exactly is brand marketing? And why is it important?[04:06 - 05:41] Why we should dive deep into brand[05:41 - 07:36] Differentiation in branding, infinitely scalable[07:39 - 11:38] When to start thinking about brand, SEO, and the funnel[13:36 - 15:36] Determining your mission and values, brand attributes[15:36 - 17:26] Speaking ways that is consistent with identity[17:28 - 19:45] Balancing different brand attributes in messaging[19:47 - 21:04] House of brands or a branded house[22:08 - 25:31] Amplifying brand marketing and the channels of choice[25:38 - 28:58] Tracking efficacy in print and non-digital formats with modern tools[28:58 - 30:47] Where to take action on Raj's adviceMentioned in this episode:Sign up for OpenView's weekly newsletterRaj Sarkar, CMO & AdvisorLinkedInTwitterSubscribe to Blake Bartlett on YouTube.Podcast produced by OpenView.View our blog for more context/inspiration.OpenView on LinkedinOpenView on TwitterOpenView on InstagramOpenView on Facebook

Chris was Snowflake’s first sales hire, and he built the commercial business from $0 to $1B+ ARR. What is the optimal relationship between a VP Sales and the Founder/CEO during this journey?Many sales leaders solely focus on hitting their number. That’s certainly important, but sales also plays a pivotal role in product strategy by acting as the voice of the customer. The goal is to achieve a collaborative push-pull relationship with founders and sales leaders that drives more customer value. Key Takeaways: [00:34 - 01:39] Feedback and writing SQL[01:39 - 02:47] Founders interacting with customers to make product adjustments[02:47 - 03:25] Pivoting based on feedback[03:25 - 04:38] Early days are less about profit, more about scaling and feedback

Chris is CRO at Snowflake and has been leading sales there for 9 years. He’s helped grow from $0 to $1B+ ARR. He’s clearly a software sales legend. So how is Chris coaching his reps and leaders during today’s recessionary environment? What should you change about your sales playbook in order to keep winning in a down market? This is the perfect episode for sales reps, sales leaders, and founders/CEOs who are looking for advice on how to navigate selling in a downturn. Key Takeaways: [01:58 - 03:52] The mindset and action plan of a great sales reps in a recession[03:52 - 05:37] A passion and conviction for what you're selling[05:42 - 07:09] Addressing specific challenges of today, adding value, saving money[07:16 - 10:29] Understanding customer pain in difficult macro environments, solving for competitor gaps[10:34 - 13:03] Don't waste people's time, have a genuine conversation[13:06 - 15:27] The business value of Snowflake's model[15:28 - 18:42] Increasing sales, driving cost savings and business value[19:38 - 26:34] How sales reps and leadership should be thinking about success[26:35 - 31:27] Pipeline generation and sales success[31:26 - 32:45] It's easy to blame others[32:45 - 36:27] Dealing with smaller budgets and cultivating empathy and problem solving[36:27 - 39:14] Preparing for 2023 budgets and planning differently

Today’s shorter episode is a follow up to my longer conversation with Alex Su, Head of Community at Ironclad. In that conversation, we talk about his TikTok channel @legaltechbro and how he developed a personal brand strategy that compliments Ironclad’s community-focused GTM strategy. So if you haven’t heard that yet, go check it out now. In today’s episode, we dive into TikTok more specifically and why you shouldn’t overlook this huge new channel.Mentioned in this episode:Sign up for OpenView's weekly newsletterAlex Su, @legaltechbroIroncladTikTokLinkedInTwitterSubscribe to Blake Bartlett on YouTube.Podcast produced by OpenView.View our blog for more context/inspiration.OpenView on LinkedinOpenView on TwitterOpenView on InstagramOpenView on Facebook