On this episode Abadesi talks to Josh Howarth, co-founder of Exploding Topics.

In this episode they talk about...

His early days as a maker and what he would change if he could do things over again

“It’s not the case that you build it and they will come. It took me two months to build and then I was like, now what? I hadn’t thought at all about marketing channels.”

Josh talks about one of the projects that he created at the start of his journey to becoming a maker. He worked on a website plugin that he had seen other people implement where you spun a wheel to see what kind of discount code you would get for entering your email.

He says that he didn’t realize how difficult getting distribution for the plugin would be and spent a lot of his time after releasing it reaching out to different people trying to get business to sign up. He achieved some revenue from it but it seemed to quickly fizzle out.

“You can usually tell pretty quickly whether it will work or not if you’re putting it out there for people to see. I probably should have quit sooner, like after two months instead of six on my previous project.”

He realized that he didn’t have any passion for the project and that it would have been better to work on something that he cared deeply about. In hindsight, he also realized that he spent too much time working on it when it was fairly clear that it would always be a slog to try to keep the revenue up.

“If the goal is to run your own business, you should go for a space that you’re interested in because someone else who is passionate about it will beat you in the end.”

The genesis and evolution of Exploding Topics and the lessons he’s learned through the process

“It’s 100 times easier to bootstrap a profitable online business if you ride one of these big market trends. You will grow with the opportunity and the competition won’t be too fierce either. That’s when I started to build a project that would spot these trends, to scratch my own itch.”

His experience with his previous project led him to research emerging trends that he could potentially build an online business out of. He did a lot of research and turned his research project into a web app when he realized that the results might be of use to other people as well.

“I didn’t intend for it to become a product in itself but I decided I had solved this problem for me, I may as well turn it into a web app and see if other people are interested in it.”

He started to post the project on the web with lists of the top trends that he was seeing at the time, which proved to be very interesting to people. One day his site was near the top of Hacker News when his database went down, leading him to scramble to upgrade to a paid solution before losing all the traffic that he was getting.

He explains what he learned and what he would have done differently with Exploding Topics if he was starting over again.

“You can feel it when you have something that people like and that is taking off. With the with the previous SaaS app it felt like I was pushing like a boulder uphill, but this thing was like snowball, everywhere I posted it people loved it and it just kept growing and growing.”

How writing updates kept him accountable as a solo founder and his advice for finding a co-founder you can work well with

“Make sure there’s a good co-founder fit, make sure that you know them and they’re going to bring a lot.”

Josh says that it was very gratifying to see people use Exploding Topics to create their own sites based on emerging trends. This was what he had hoped to do with his original project with the web plugin.

He says that it was important as a solo founder to write updates on Medium for his users. This encouraged him to make sure that he was making progress consistently on the site, because he needed to show his users and readers that he was always working on it. He also heard a lot of useful feedback from users who would use the site and sometimes even from people who were simply following his journey.

He ended up taking on a co-founder for Exploding Topics via the sale of his site. He explains what the most important attributes in a co-founder are and why he and his co-founder work well together.

“Writing updates and keeping people updated on your progress is fantastic as a sole founder because it keeps you accountable. It also helps to clarify your thoughts and direction. It helps to get support from other people who reach out to offer support, advice and guidance.”

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. 😸

On this episode Abadesi talks to Matthew Paul, software product designer, researcher, and front-end engineer. He’s a former product designer at InVision, he’s worked on software and design systems at IBM, and has designed prototypes at Apple.

In this episode they talk about...

The open-source design project he’s working on, and how to make good design more accessible

“As a designer you always have to bring the customer back to the conversation, and you have to invite the engineers, product directors, VPs, into your conversations with the customers, and let them hear what the customers have to say.”

Matthew points out that type is being used on screens in more and more places these days, including in non-traditional places like in heads-up displays in vehicles and in VR headsets. He says that it’s important to make sure that good type is accessible to everyone, everywhere, and explains how the project he’s working on will enable that.

Common design pitfalls to avoid and advice for working with designers

“Seriously, don’t be afraid to ask for help. At a decent company, at a decent place, no one’s gonna get dinged for asking for help. You’re going to get dinged, not right away, but you’re going to get dinged if you don’t. You just end up burning out or not doing a good job at any of the things.”

He runs through a bunch of different common mistakes that people make when they’re designing a product or working with a design team. He walks through some projects in the past that he’s been a part of that didn’t work out as intended and what the key issues turned out to be on those teams.

“Don’t run a design sprint unless you actually know what it is and how to do it and have a plan to make it successful.”

He explains the right ratio of designers to software engineers, saying that you want to usually have one designer for every eight software engineers. He also talks about the pitfalls of running a design sprint without really knowing what you’re doing.

He also talks about what it means to be “neuro-atypical” and why we need more inclusion of different thinking, learning, and communication styles in the workplace.

“They expect them to be a certain person, to fit a certain mold, to have good executive functioning, to have a set of cognitive processes that allow you to work in a linear fashion. The fact is, our brains are not all built that way. That’s neurodiversity.”

How he’s working on his personal development and where he learns the most

“I try to meet new people. I literally have gotten every single job that I’ve ever had through Twitter, just through them reaching out to me, me reaching out to them, and introductions happening that way.”

Matthew explains the evolution in his thinking over time on how best to keep up with the latest trends in design and says that he used to follow all the blogs very closely when he was younger but has moved away from that as he’s grown as a designer.

He offers a book recommendation if you’re interested in getting into typography, and says that he learns the most from other people. He tries to travel often to be exposed to new people and talk to them in person about what they’re working on.

“I think I just learn the most from meeting new people and hearing what they’re working on — taking a little spark of what they’re working on and seeing if I can include that in my work.”

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Headspin Mobile for their support. 😸

Books and Products Recommended in This Episode

1Password — Save your passwords and logins with one click.

AirPods Pro — New AirPods with active noise cancellation.

Detail in Typography by Jost Hochuli

Headspace Sleep — Sleep section of the popular meditation app.

Magnet — Window manager for Mac.

Simplenote — Simple, lighter alternative to Evernote.

On this episode Abadesi talks to Pieter Levels, founder of Nomad List, a global community of international travellers working around the world, RemoteOK, a job board for remote jobs, and Hoodmaps, a unique neighborhood map app.

In this episode they talk about...

Bootstrapping versus VC, and why he doesn’t want to build a team around his products

“I don’t want to lose my skills. If I stop making stuff and become a manger, I’m going to learn a new skills but I’m not a business guy. I’m a creative person. I get happy from making stuff that works and people use.”

Pieter says that he originally thought about creating a venture-backed business, which was going to be a proto-Uber in Amsterdam, before he pivoted to bootstrapping businesses. They discuss the questionable ethics of big venture-backed businesses who have often had to compromise on their values to get really big, really fast.

He says that he works with one other person on his products but otherwise works on them all on his own — and he likes it that way. He explains why he doesn’t want to become a manager and instead prefers to keep working on his current products and potential new ones on his own, instead of delegating them to someone else once they’ve become successful.

The difference between creating a website and building a community, and how to think about charging for your product

“It’s psychologically difficult to charge people money.”

He talks about how Nomad List has evolved over time and the features he has added to the site. He explains how it transformed from a website to a community. He breaks down the benefits of a community in expanding the reach of a movement and the intangibles that a community brings with it.

He talks about how he got over the psychological barriers to charging money for access to a community, and says that at one time he explained to a member that he was even somewhat embarrassed to be charging, though now he hears from people all the time about the value that it brings to their lives. He also talks about the difficulty of managing and moderating a community.

What the future of remote work and the digital nomad lifestyle will look like

“You start off as a nomad thinking that you are going to travel the world forever but you go insane if you travel too fast.”

Pieter talks about the evolution of the digital nomad lifestyle from its infancy to now, and why it’s being talked about more than ever. He says that it was at one time a somewhat fringe movement and that he never expected it to expand like it has.

He says that creating the community around the lifestyle has helped accelerate its acceptance in mainstream culture and has resulted in there being more resources than ever for digital nomads.

He says that in time we won’t be calling it nomadism anymore, it will just be something that becomes a normal part of life as remote work gains more and more acceptance. He says that eventually “digital nomadism” will become a term like “netizens” (an early term for people who used the internet) that we don’t use anymore, because it is so pervasive, just like the internet has become.

“I flew less than my Dutch friends last year. Travel’s really fun but it’s more about finding a place where you feel better than where you were born and grew up.”

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Headspin Mobile for their support. 😸

On this episode Abadesi talks to Waseem Daher, founder and CEO of Pilot. Pilot is bringing bookkeeping into the modern age. He has started (and sold!) two other companies prior to Pilot.

In this episode they talk about...

The story of starting Pilot and what Waseem learned from his two previous companies

“The end-to-end solution is really what made the business work. We are going to be your bookkeeper, your finance team, rather than sell you software.”

The story of Pilot goes back to his first company, where they tried to do their books themselves, but realized how tedious it was and how much could be automated.

He explains why he tries to have a more focused approach to company-building now:

“I try to have a better sense of what is actually important. We were so worried about all of the stuff that we thought represented an existential threat but in practice literally zero of those things mattered. Of all the things I remember agonizing about, none of them had any actual effect on the business.”

He also says that he makes sure to take time to rest and recharge, rather than working all the time:

“In the first company we worked all the time, 6 days a week, 12 hours a day. Despite having worked that long, there were Saturdays where I still felt behind so I worked then as well, and every time I did that, it was always a mistake.”

When it makes sense to take venture capital versus bootstrap a business

“There’s a very pervasive and harmful narrative in Silicon Valley that the VC way is the only way to do it. I actually think the VC way is the unnecessarily difficult or hard way.”

Waseem explains how to think about starting a company and talks about the principles to keep in mind when you’re thinking about the risk and reward of different approaches:

“If your objective is wealth creation, you should not start a startup, you should go work on Wall Street or something. The easiest way to make $10M is to own 100% of a company that’s worth $10M, not to own 1% of a company that’s worth $1B.”

He says that “lifestyle is not a bad word” and that as a founder you don’t need to care about serving a massive market unless you’ve taken venture capital funding.

“Venture capital is not right for 99% of businesses. You have to be building something that is targeting a gigantic market to have a company worth billions of dollars doing hundreds of millions of dollars of revenue.”

How to think about a potential acquisition

“By raising a bunch of institutional capital, you’re prevented from taking exits that are otherwise very good or very profitable.”

Waseem shares what he’s learned from two previous exits, one to Oracle and the other to Dropbox. He says that it’s most important to think about how you and your company will mesh with the acquirer and choose the offer that provides the best fit rather than the highest dollar amount. He says that if the fit is good, you will create much more value through the relationship together than the value of the acquisition.

“Look at the acquisition as the start of a new relationship, not the end of something.”

How Waseem stays productive

He explains that he keeps most of his apps on his phone in folders rather than on his home screen. This creates friction and ensures that he has to be intentional about what exactly he is doing when he takes out his phone.

He also explains exactly how to write emails that get responses from busy people:

“Craft something that is really short, that is to the point, and that has a very crisp and clear call-to-action at the end of the email. Ideally the call-to-action is as easy to respond to as possible.”

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Headspin Mobile for their support. 😸

On this episode Abadesi talks to Ethan Eismann, VP of Design at Slack. He has previously worked on flagship products at Google, Uber, and Airbnb, as well as at Adobe back when Flash was still a thing!

In this episode they talk about...

The consumerization of the enterprise and bringing personality to software

“You need somebody who is really able to think of your customers first and who can translate your customers’ perspective into your own unique tone and personality.”

Ethan talks about the trend of the “consumerization” of the enterprise, why workers are demanding better software, and how Slack has played a role in the trend. He talks about how they’ve brought some personality to software that is typically utilitarian, to the delight of millions of users. Ethan tells the story of the pivot that Slack made from being a gaming company called Glitch to a communication tool for the enterprise. He also talks about how one of the early employees helped to shape the unique personality that Slack has today.

The design philosophy at Slack and how they use hypotheses in designing their products

“It’s critically important to have a perspective on what your customers need. They will often tell you where to focus. They have these unsatisfied needs and deep wants and desires. They will tell you the path.”

Ethan breaks down the design philosophy at Slack, explaining some of the unique processes that they use to develop software. He says that they iterate rapidly, and are constantly testing new features on their own live data from their internal Slack channels. He says that they encourage their engineering teams to contribute design ideas as well.

“We try to keep a history of our prototypes and we document the learning that comes along with each prototype. We have a library of the past experiments that we’ve tried and what we’ve learned.”

He explains their process for testing their hypotheses and how they determine what to do based on the results of their experiments. He says that sometimes they find unexpected results which change the direction of their efforts.

“When you're thinking about your product, consider that people only have so many cognitive calories to spend at any given moment. If you have a complex product that could be okay, as long as you break it down into simple concepts that people can consume.”

Customer-centric design and what it means to communicate energy as well as information

“Fundamentally, the companies that have been most successful are the ones that have prioritized their customers. They’re always making time every week to get closer to customers. Having a customer-centric company means that everyone has a perspective because everyone in the company is spending time with them.”

Ethan talks about the importance of listening closely to what your customers have to say. He says that at Slack they are constantly co-creating with their users. He breaks down exactly how they do this, including how they uses shared channels to interface with power users around the world who are always sharing feedback and helping them shape the direction of the product. He also breaks down why communication is not only about information, how they are using things like emojis to communicate energy in addition to information, and how this is allowing workers to express their unique voice.

“Communication is information as well as energy. Software tools are often great at allowing you to create information but don’t always let you express energy. We try to design in a way that allows individual personalities to shine.”

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Headspin, Safety Wing, and Trulioo for their support. 😸

Companies and Products Recommended on This Episode

OP-Z Synthesizer — An advanced fully portable 16-track sequencer and synthesizer.

OXO Spatulas — Designed to serve dishes with comfort, efficiency and style.

Slack Shared Channels — Allows Slack teams in different organizations to use Slack to collaborate together as easily and productively as they do internally.

On this episode Abadesi talks to Michelle Bacharach, founder and CEO of FINDMINE, a retail technology company that uses machine learning to scale the currently manual and tedious process of product curation. They are a fast-growing company with clients like Adidas, Perry Ellis, and Callaway.

In this episode they talk about...

What led Michelle to found FINDMINE, and how they’re changing the buying experience

“We’re trying to close the information gap between the customer, who isn’t an expert on what they’re buying, and the brand, who is an expert at what they’re selling. The customer gets better information and spends more money and the brand is happier because they make more revenue and they save time."

The inspiration for FINDMINE came from Michelle’s experiences as a shopper. She says that she struggled with buying things that might have looked intriguing at the point of purchase, but realized later that she didn’t have the use for it that she thought she did, or it didn’t work with the rest of her purchases, as with a couch that didn’t match. She says that she started the company to help the people at companies who know the most about products and their potential use cases transfer that information to the buyers of those products. She says that they are using machine learning to hone the marketing campaigns for products and in the process saving time for those selling products and increasing customer satisfaction on the buyer’s side.

“Artificial intelligence and automation are very valuable when there’s a bottleneck of human effort, and we scale out creative human effort. The starting point is a human they set the vision for what this fashion brands stands for and how they define style.”

Her advice for startups pitching big companies as potential clients

“Pitch the companies that you’re trying to land as clients. Maybe one takes a chance on you and if nothing else, you’re going to learn a lot, like what features are important and what the product feedback is.”

Michelle explains how, as a relatively young company, they have landed contracts with so many big-name brands. She explains the process that she used to pitch them, and talks about her key pieces of advice for smaller companies pitching bigger ones. She says that it makes sense to aim for clients that have fewer legal requirements for suppliers when you’re just getting started.

“People don't necessarily always know they have a problem or the severity of the problem that they have or how to tackle it. You can get analysis paralysis from a customer sometimes. When they realize there's a problem, that's half the battle. They may realize we are the solution, but they don't know how to start using the tools.“

How to close enterprise customers

“It’s so funny because our whole mission is to help the buyer understand how to be successful with the product that they’re buying and that’s exactly the same thing that we have to do for our customers. They have less information about how to be successful with our FINDMINE technology than we do and we have to close that gap for them. It’s so full circle.”

She walks through the process of landing a client from the initial pitch to signing the contract. She says that it’s important to educate your customers on the true value of the product to them when they don’t know exactly what kind of problem they have or how to solve it, let alone with new technologies that they may be unfamiliar with. She talks about the value of case studies and why successfully landing just one client can lead to many more.

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Headspin, Safety Wing, and Trulioo for their support. 😸

On this episode Abadesi talks to Ryan Simonetti, co-founder and CEO of Convene. They call themselves commercial real estate’s first workplace-as-a-service platform. He co-founded the company in 2009 and have raised $260M in funding to date. He is also an investor in and advisor to tech startups.

In this episode they talk about...

The story of founding Convene and his advice for finding a co-founder

“Partnerships evolve over time. You have to be open-minded enough to go on that journey together.”

Ryan grew up in an entrepreneurial household and worked in the finance and real estate industries in New York City where he saw an emerging need in the space. He says that they’ve seen lifestyle becoming a primary concern for people that they view their clients as users rather than as customers. He co-founded the company with his business partner and long-time friend Christopher Kelly, intending to disrupt the commercial real estate industry. He also explains his philosophy for finding a co-founder.

“When thinking about choosing a co-founder, you have to know yourself first. You want to make sure that you are aligning yourself someone who is complementary.”

How they have created a strong company culture and the importance of gratitude at Convene

“We obsess over customer experience but we put that same energy and attention into team member experience.”

Ryan explains how they have created a team that can deliver the consistently high standards expected by their members. He says that it starts with the right culture and philosophy, which means hiring the right people. He says that building the right culture begins even before someone is hired. It starts right at the initial interview process, where they eliminate candidates if they don’t meet the high standards that Convene has for culture.

He also talks about the culture of gratitude that they have instilled in the workforce and says that their executives pass around handwritten notes about what they appreciate that other team members have done.

Ryan’s predictions for the future of work in an increasingly distributed world

“I think that there is a whole generation of companies today that are being born that will never sign a lease for their own office and will outsource to companies regardless of how big they ever get. It’s remote-first and experience-first.”

He explains the three big trends that he says will define the future of work and explains the implications for his business of the remote-first companies that are being created around the world.

“Even though the future of work will be more distributed… no matter what happens, place will continue to be really important in the future of work.”

How he is investing in his personal development

“Don't be afraid to ask for help and surround yourself with people with more experience than you. Never be afraid to steal wisdom. I like to think of myself in the wisdom theft business — the more I can steal, the smarter I feel.”

Ryan says that it is important to him to relax and de-stress, and that this is part of the key to his productivity. He also explains how he makes time to be present with his wife and children consistently. He also says that he was not afraid to “ask dumb questions” when he was a first-time founder starting Convene. He credits surrounding himself with mentors and coaches that he could ask for advice for his success thus far, and suggests that founders do the same.

He also talks about some of his favorite products and a great book that he read that helped him as he scaled Convene.

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Headspin,Safety Wing, and Trulioo for their support. 😸

Companies, Products, and Books Mentioned in This Episode

Blinkist — Key insights from 2,000+ non-fiction books.

Headspace — Meditation made simple in just 10 minutes a day

Peloton — World-class indoor cycling wherever you are.

The Messy Middle by Scott Belsky

On this episode Abadesi talks to Jill Salzman, founder of The Founding Moms, a “global collective of offline masterminds and online resources for mom entrepreneurs.” She was formerly the founder of a music management firm and was also the creator of a line of baby jewelry.

In this episode they talk about...

The story of the creation of The Founding Moms and how it’s helping mom entrepreneurs around the globe

“No one wants to say that they’re a mom entrepreneur. They’re an entrepreneur. They don’t like to use the word mom. They don’t want people to know they’re distracted by kids. There are tons of moms who are making things but don’t want to say it because nobody else is.”

Jill tells the story of the businesses she founded prior to this one, including her time managing bands and how it was akin to building communities, although in a very different manner than she does today with The Founding Moms. She says that the community and business grew out of an inauspicious beginning after she created an informal meetup in Chicago for moms with businesses.

She was surprised at the number of people who showed up and also that there were people from outside her city who were requesting a chapter in their own cities. The Founding Moms has since grown to include countries around the world, with chapters in Singapore, Guatemala, and more.

“I posted on Meetup and I said ‘if you’re a woman with a business and a baby, please come have coffee with me and tell me how you’re doing it because I think I’m going to lose my mind.”

How she grew the community and her advice for those who are new to community-building

“I think we need to eradicate the idea of networking being a dirty word.”

Initially, Jill showed up to the meetups without a formal plan or agenda for what should take place. She realized that when she showed up with a piece of paper with handwritten notes, people commented on how organized she was. She then started showing up with a printed piece of paper, and has since created much more structure for the meetups.

She says that in her case and for those new to community-building, it’s best to show up and listen and ask a lot of questions of your community members. If you listen to them, they’ll tell you what they need and lead you to the ways that you need to change to grow the community further.

She explains why you shouldn’t feel the need to include absolutely everyone in your community and why in fact it’s actually best to set yourself a goal to make sure that the wrong types of people are not feeling a part of the community.

She also gives her advice on branding, outreach, and content marketing.

“I know in my heart of hearts ten years in there is nothing that trumps meeting up in real life at all.”

How she approached the decision to charge for access and subsequently increase prices, as well as how she stays productive

“If you learn to lean on the community and become a little more vulnerable than you’re used to, I can’t tell you how exponentially you’re going to grow.”

Jill talks about the thought process that went into deciding whether to charge for access to the community and how she came up with the number that she would charge per month. She started at $10 and has since increased it to $35. She says that everything she does is “literally trial and error” and that she simply Googled what other communities were charging. She explains why you shouldn’t be afraid to charge for your community and how to overcome your fear that your members will leave if you do so.

She also explains how she manages her schedule, why she uses three (!) virtual assistants and the work they each do, as well as how her team of contractors at The Founding Moms works together.

“I have three virtual assistants. I am a huge VA proponent. I think you’re all missing out if you don’t have one because they’re extremely affordable and amazing at getting things done for you.”

She also talks about some of the products she’s loving right now.

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Headspin for their support.

Companies and Products Mentioned on This Episode

Loom — Seamless screen, mic, and camera recording for Chrome.

Marco Polo — Find your phone by shouting MARCO!

Slack — Be less busy. Real-time messaging, archiving and search.

On this episode Abadesi talks to Brianne Kimmel, founder of Work Life, an early stage venture firm in Silicon Valley that invests in tools and services for the modern workplace. She was formerly head of product and GTM strategy at Zendesk.

In this episode they talk about...

Why she started Work Life and what she learned while fundraising

“There are a lot of non-traditional folks who are breaking into venture, many of which are solo GPs.”

Brianne started angel investing on the side when she was working at Zendesk. She enjoyed working with and meeting new entrepreneurs so decided to start her own fund to “do what she was doing on evenings and weekends full-time.”

She explains the focus of the fund and talks about the fundraising process for it. Initially, she says, she started with a “friends and family'” round before she became comfortable raising from other people. She started pitching to people outside her network and tried to run a “tight process.” She explains her strategy for follow-up and why her personal productivity regime was such a big part of her pitch. She also talks about why she created her own list of questions that were often asked by potential investors and how she continually weaved those back into her pitch deck.

“The list of FAQs kept getting smaller because the pitch was getting incrementally better every time I give it.”

No-code tools, distributed teams, and the future of work

“Only 0.5% of people can code, so for the 99.5% of us code is actually a real barrier.”

Brianne is passionate about no-code tools, especially those that can help employees be more productive in the workplace. She talks about the importance of growing “bottom-up” in the enterprise market and talks about some of the companies she’s investing in that are employing that strategy.

“Increasingly, startups will compete on culture and culture alone and having great tools and creating a very inclusive work environment is one great way to do that.”

She also talks about some of the tools that are enabling remote work and why more and more early-stage teams are going fully distributed. She says that people are traveling more, the world is getting smaller, and people who formerly didn’t have flexibility at work now have the flexibility to work from home or anywhere else in the world.

“The question is not, ‘can you find enough work?’ It’s, ‘can you find the right problems that you want to work on?’”

How she’s building a community around her fund

“People are a little bit tired of networking. They have to be the best version of themselves at all times and come in very confident but you end up leaving with something that doesn’t feel truly authentic.”

Brianne started building communities while at Zendesk. She also runs a program called SaaS School in San Francisco. She talks about how she built a community of fellow product managers who met regularly in an informal setting where they could be open, authentic, and vulnerable with each other. She says that she’s doing the same for her fund and explains why it’s important to build a community when investing. Brianne also gives tips for fellow community-builders.

She also talks about some of the products she’s loving right now.

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts.

Companies and Products Mentioned on This Episode

Bunches — The easiest way to start a paid group chat about anything.

Canary — A complete security system in a single device.

Chroma Stories — Create stunning and engaging stories with easy-to-use tools.

Deep Sentinel — A robust, AI-powered home security system.

Muze — Messaging and social media platform.

On this episode Abadesi talks to John Henry, venture partner at Harlem Capital and host of Hustle on VICELAND.

In this episode they talk about...

How he got into entrepreneurship and how the expectations for today’s entrepreneurs have changed

“I think the world of business and entrepreneurship can seem pretty scary these days. There's so much at stake, you got to get it right, you got to raise money, you got to go public.“

John got his start as an entrepreneur through trying to help out his family when he was young, starting a dry cleaning service in New York. He says that he didn’t have big aspirations at the time and that he didn’t come to entrepreneurship with visions of a glamorous lifestyle in his future.

He says that these days entrepreneurship can seem very daunting and that rather than feeling the weight of the expectations that people have you should instead take the approach of doing something creative and fun and then see if you can sell it to folks.

“I have to be honest, if I were starting now versus a decade ago when I started I might feel like the weight of the the expectation might have crushed the seed of enthusiasm that I had to start.”

Why he says getting a regular job is riskier than starting a company

“There are a lot of macroeconomic changes and not only are older corporations cutting jobs but you also see it in new companies. For me taking a normal job felt riskier because your own income was not in your own hands.”

When John started working he realized that it would be better for him to put his time and effort into building a company instead of putting it into working for someone else at a conventional job. He says that although it can take years to get off the ground, it’s nevertheless better to work at something that you own entirely.

How he discovered financial literacy and how to be a “multi-dimensional earner”

“I’ve discovered this entirely new way of earning that I never would have known about when I was a doorman ten years ago because back then my best understanding of how to earn income was clocking in.”

John says that he is investing in assets rather than experiences these days. He says that through doing so he wants to “build something for your family that can’t be taken away.” He explains how he learned about how to effectively invest his money after coming from a disadvantaged background where he didn’t normally have much exposure to those types of concepts.

He also talks about how to find a good business idea for aspiring entrepreneurs and how he has diversified his income streams so that he’s not reliant on any one of them. He explains that he is making sure to “circulate” the funds that he earns so that he’s always re-investing and putting them to work instead of just stashing them away in a savings account.

“You have to meet the moment. For anyone who is listening who is curious for one reason or another what they can do to earn income, look around at the moment. There are a lot of changes that are specific to right now, to 2020.”

The history of VC and how they’re changing the flow of capital to underrepresented founders at Harlem Capital

John explains some of the ins-and-outs of venture capital and the history of the space including how it came to be that a “handful of zip codes and a handful of schools determine which companies go public.” He explains what kinds of barriers to entry exist for people who find themselves outside of the networks of privileged people with connections to the large institutions that normally contribute to venture capital funds (yes, venture capitalists have to fundraise too!).

He also talks about how he invests in personal development and talks about some of the products he’s loving right now.

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts.

Companies and Products Mentioned on This Episode

LED Ring Light — Beautifully lit photos and video calls.

Nespresso — The connected espresso machine.

Sodastream — Carbonated water, at home.

On this episode Abadesi talks to Kathryn Duryea Wyndowe, founder and CEO of Year & Day. They make beautiful tableware that they sell direct-to-consumer online via their website.

In this episode they talk about...

How she came up with the idea for Year & Day

“I felt very empowered by this idea of buying a new set of plates outside of this proposition of getting married and a wedding registry.”

Kathryn graduated from Stanford GSB and started working at Tiffany & Co., helping to bring them online. She was inspired by the new direct-to-consumer brands and had always loved the ritual of setting the table. She decided she wanted to make “tableware fun again.” Through trying to buy a set of tableware for herself, she found that the experience was confusing and uninspiring. After going through that, she “turned on the other side of her brain” and dug into the market for tableware, which accounts for $7B in annual spend, which led her to start Year & Day.

Her crazy year preparing to launch the brand

“It took about 11 months, almost a year, to go from basically this is my full attention, full-time professional endeavor to now we are selling to customers.”

Kathryn thought that she could launch in eight months, but it actually took almost a year. She talks about the wide range of tasks that she had to tackle, basically by herself, from design to manufacturing to fulfilment to arranging for web development. She talks about “fighting against the inertia of the world” to will the brand new company into existence. She says that her launch strategy was to email 500 of her friends about the company and that in the beginning she had her brother doing customer service. Since then they’ve grown to a team of 8 based in San Francisco.

“All aspects of starting a business are both wildly thrilling with high highs and low lows and real challenges, but what's so exciting about those early months and days is that this idea that you formulated, now you're starting to bring it into shape into the real world.”

The power of Instagram and the rise of direct-to-consumer

“A lot of the product discovery these days happens on social media on platforms like Instagram. People are relying more and more on people that they follow there to help them discover products that they’ll love, that suit their lives.”

The rules for marketing to the digital-native generation have changed with the advent of social media platforms and influencers. Kathryn explains why Instagram is such a powerful platform and why people are gravitating towards a different kind of shopping experience. She talks about the importance of curation when it comes to products like tableware.

She also talks about some of her favorite productivity hacks, including why she meditates, works from home one morning a week, and why she still uses good old fashioned pen-and-paper for her to-do lists.

“As an entrepreneur you could literally work 24 hours a day and still feel like your list is growing, so in order to have a healthy balance you need to actually set some boundaries.”

She also discusses some of her favorite products.

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Big thanks to Knowable for their support. 😸

Companies and Products Mentioned on This Episode

Audm — The world’s best longform journalism, read aloud.

Insight Timer — The best free meditation timer.

Snagit — The best screen capture software.