Startup Happy Hour

One of the challenges facing gig workers and hourly workers today is to get paid regularly and on time. Nico Simko founded Clair to solve this problem. It’s a platform built to provide instant payment to hourly and gig workers.

Nico explains what on-demand pay is and how it works, and what Clair’s overall mission is. He dives into some of the tools and features the platform offers to workers and outlines instant payments. He also talks about upcoming new features and how Clair could shape the payments space as a whole.

Nico also talks about his journey from working for J.P. Morgan to becoming an entrepreneur, the lessons he has learned from being a founder, and what he thinks made Clair a success.

In this episode of Startup Happy Hour, we’re talking to Rafael Cosman, the founder and CEO of TrustToken. Decentralized finance and cryptocurrency are grabbing headlines all over the world today, and Rafael is here to share his insights about this space and what TrustToken is aiming to do.

He explains what TrustToken is and how it works, and we talk about the importance of crypto and what it means for the overall economy. Rafael shares some ideas on how decentralized finance can solve many of the problems with today’s financial systems, and outlines some of the advantages of crypto over fiat money.

Rafael also talks about what compelled him to create TrustToken and tells us what’s next for the project. He gives his predictions on where the decentralized finance space will be in ten years and talks about his journey as an entrepreneur along with some lessons for aspiring founders.

In this episode of Startup Happy Hour, we’re talking to Mike Cheng. He is the co-founder and CEO of a company called Lumen5, which is one of the fastest-growing companies in Canada right now.

Their goal is to democratize video production by helping over 700,000 companies, including big brands like Salesforce, SAP, and Forbes, create high-quality and ready-to-publish videos in minutes.

We talk about Lumen5, how it got started, and what it does, along with how someone can get started making videos on the platform. Mike explains some of the different features and tools, and we discuss who is using the platform right now.

Mike also gives his views on how this space looks set to evolve over the next ten years, and we dive into the future of VR, and VR social media. Mike shares some of the challenges involved in a company that grows so fast, along with his experiences as a founder and any lessons he learned along the way.

In today’s episode of Startup Happy Hour, we’re talking to Celine Tien, Founder and CEO of Flowly, an app for managing your pain and anxiety.

Celine takes us through how Flowly works to help people with chronic pain and anxiety, and explains how people can get started with the app. We discuss the types of people who are struggling with chronic pain and how they’re using Flowly to manage it better.

Celine also shares what inspired her to start working on the app, like her parents’ background in medicine and biotech, and early experiences with pancreatic cancer patients. She talks about her strategies for building a customer base, and how the pandemic impacted both building the app and attracting users.

We touch on the fascinating topic of biofeedback and VR, and how this combo could be used in the next decade and beyond. Celine talks about Flowly’s exciting plans for the future, about her background in the film industry, and how she transitioned into being an entrepreneur.

In today’s episode of Startup Happy Hour, we’re talking to Dan Burcaw. He's the co-founder and CEO at Nami ML, which is a service that helps you launch, scale, and optimize your mobile app subscription business.

Dan talks to us about what Nami ML is, how it works, and what exactly it does. We talk about how to maintain the value alignment between brands and consumers over a long period of time — something even giant brands struggle with.

Dan shares some of the most common mistakes that he’s seen subscription businesses make, and talks about some communication best practices for a subscription business, like email frequency. He tells us what sets Nami ML apart from similar businesses, and talks about his experiences running a business during the pandemic.

Finally, we discuss where the subscription space could be in a decade or two, and Dan shares some advice for any young people who aspire to be a founder one day.

David Sun is the CEO of Proof of Beauty, a community-driven crypto art project that builds commentary on crypto using crypto itself as the artistic medium.

In this episode of the Startup Happy Hour, David shares insight into how crypto art is allowing creatives to become more creative, empowered, and able to reach wider audiences. He also dives into where he sees blockchain technology and crypto art going in the next ten years, and explains why he believes that blockchain is helping people work together in a way that transcends culture, language, politics, and more.

Tune in to hear David talk about being interested in creating but not in being a founder. He also shares why he always prioritized working in organizations that push the very idea of work, and discusses how people will be able to understand NFTs more when they lose the tangibility of value.

Matthew Yahes is CEO at Extend Your Team, a company that connects remote workers for mid- to upper-level positions with US-based companies and entrepreneurs.

In this episode of the Startup Happy Hour, Matthew talks about how his personal experience with needing to hire an experienced management professional spurred the idea of starting Extend Your Time. He explains his process for onboarding the best remote talent, and shares how that has led to him achieving a 95% success rate of matching remote workers to companies on the first try. Matthew also provides advice for hiring the right candidate, starting out a company remotely, and dealing with the inevitable ups and downs of running a startup.

Tune in to hear Matthew’s thoughts on why LinkedIn is the best tool for building out your network remotely, why a decentralized, global workforce is a good idea for any company, and why aspiring entrepreneurs should spend a few years working for and learning from someone else first.

Niket Desai is a serial entrepreneur and mastermind behind design and product strategy at Time by Ping, a platform that leverages AI and machine learning to free lawyers from manually tracking their billable hours.

In this episode, Niket shares his experiences transitioning from investor to employee at Time by Ping, taking a risk by founding a company right out of college, and making large scale innovation commonplace in India through Flipkart. He also dives into the importance of finding the ‘why’ in everything, which is what drove him to adopt a non-traditional title at Time by Ping and create his own roles in previous companies.

Tune in to hear Niket discuss why universities need to invest in their own talent, what his day-to-day working in product and design looks like, and printing a physical book of all the tweets he’s ever tweeted.

Patrick Gardner is the CTO at Time by Ping, a platform that leverages AI and machine learning to free lawyers from manually tracking their billable hours.

In this episode, Patrick dives into the technology behind Time by Ping. He explains why timekeeping can be instrumental in reducing incentive misalignment and increasing productivity in lawyers, and shares what it was like leaving his 20-year-long role as SVP at a large corporation to transition into a leadership role at an early stage startup.

Tune in to hear Patrick talk about the future of the billable hour in the legal industry, the most surprising thing he discovered from working at Time by Ping, and his advice for others looking to work at a startup for the first time.

Brian Flynn is the Co-Founder and CEO of RabbitHole, a company that educates users on crypto by taking them through a task-based journey that allows them to earn crypto by completing tasks.

In this episode, Brian shares the reason why he decided to tackle the gap in crypto education, dives into the present and future significance of NFTs, and discusses using crypto in the context of media businesses.

Tune in to hear Brian talk about what our digital lives could look like in the future, universities being built on the chain, and whether he thinks NFTs are a bubble that will pop.

David Kobrosky is the Co-Founder of intros.ai, an introduction infrastructure company that facilitates connections between individuals in existing communities.

In this episode, David chats about the role and importance of intention when forming a relationship. He dives into his thoughts on what connection and meeting people will look like in the future, and touches on the gap that is being bridged between NFTs and digital communities.

Tune in to hear David describe what it was like starting his first company in middle school, share how he was able to land a job with Gary Vaynerchuk during university, and provide insight into the thought process that went into dropping out of university, twice.

Jeffrey Silverman is Co-Founder and Managing Partner at Laconia Capital Group, a venture capital firm that invests in B2B startups at a seed-stage level. Laconia is sector agnostic, but they focus specifically on startups that are building technology to replace analog workflows.

In this episode, Jeffrey talks about how he first stumbled into his venture fund and why he decided to invest exclusively in early-stage startups. He also provides insight into his process for determining which startups to invest in and compares the startup pitching process with going on a first date.

Tune in to hear Jeffrey dish on what his day-to-day as managing partner at a VC firm is like. He shares his take on trends he sees taking off in the startup space in the future, and explains why being able to handle rejection is a crucial skill that can lead to great outcomes.

Peter Voss is the CEO and Founder of Aigo.ai, an AI company that centers around creating intelligent chatbots with human-like abilities, such as memory and reasoning.

In this episode, Peter shares insight into how artificial general intelligence differs from regular AI. He explains that while regular AI relies on the intelligence of an external party, such as programmers or designers, artificial general intelligence builds intelligence directly into the computer.

Tune in to hear Peter talk about what he believes artificial general intelligence and Aigo will be capable of doing in the future, his approach to morality and how it applies to Aigo, and the challenges and obstacles he anticipates facing as Aigo becomes more widely used.

Eddy Badrina is the CEO of Eden Green Technology, an agriculture technology company that provides food suppliers and distributors with patented hardware and proprietary software to put in their warehouses and controlled environment facilities.

In this episode, Eddy dives into Eden Green’s mission to change the way that people farm food and feed people. He describes the technology they use to support this mission, and provides insight into the issue of food insecurity in the US.

Tune in to hear Eddy’s thoughts on how Eden Green’s technology will impact food insecurity over the next ten years. Learn from his experience bootstrapping a company, selling it, and buying it back again, and his advice for founders at a crossroads over what their next steps should be.

Christiana Cromer is the Marketing Manager at Coiled, a software company that increases access to scalable computing and equips data scientists with the tools they need to solve problems quicker and more efficiently.

In this episode, Christiana explains the connections between Coiled, Dask, and Python. She dives into what differentiates Coiled from its competitors, and shares her thoughts on where the technology behind Coiled and Dask will be in the next ten years.

Tune in to hear Christiana describe her experience working as a non-technical marketing manager in a highly technical industry. She also provides insight into why marketing and community building go hand in hand, and sheds light into her plans for starting her own company one day.

Rachel He is a product designer on Spotify’s Podcaster Mission team, a team that focuses on various podcaster-related services including podcast creation, distribution, and analytics.

In this episode, Rachel shares her day-to-day as a product designer. She describes her experience working on a startup-like team within a big company, and details her journey transitioning from studying computer science to becoming a product designer.

Tune in to hear Rachel dive into her thoughts on the environmental impact of the cloud and what designers in all industries can do to design sustainably. She also talks about how climate and race are linked, and whether there should be an ethics requirement in tech.

Jonah Erlich is a software engineer at Bubble, a no-code platform that allows individuals to build a full stack web application using a drag and drop interface.

In this episode, Jonah dives into how no-code makes it possible to build on the front-end, back-end, and database without writing a single line of code. He shares his thoughts on what no-code will bring to the future, and elaborates on his role as a coder working at a no-code company.

Tune in to hear Jonah talk about how no-code and blockchain perfectly collide, what it was like building a VC organization from scratch, and the importance of creating and finding meaning in everyday things.

Sam Norton is the Founder of Heron Farms, an indoor vertical farm that takes an untraditional approach of using saltwater to irrigate plants.

In this episode, Sam gives listeners an overview on the basics of saltwater agriculture, shares his thoughts on how he expects the industry to grow and progress in the future, and provides insight into the environmental impacts of using saltwater over freshwater to irrigate plants.

Tune in to hear Sam dish on the future of Heron Farms, managing team dynamics at a growing startup, and going a full year without having a cell phone.

Michael Kovalcik is the Director of Operations at KODE Labs, a smart building software startup that optimizes commercial buildings’ energy usage and operations to create a sustainable and comfortable environment.

In this episode, Michael shares a behind-the-scenes look into the elements that make up building management, provides insight into how KODE Labs is disrupting the industry, and describes what his day-to-day as Director of Operations looks like. Tune in to hear Michael explore the concept of a net promoter score for cities, his opinion that the worst thing a bad product can have is good marketing, the idea that rent is essentially a subscription cost for living in a city, and more.

Arthur Shi is a software engineer at Snowflake, a cloud data platform that underwent a successful IPO last fall.

In this episode, Arthur shares insight into cloud data and, specifically, how Snowflake is revolutionizing the space. He also dives into how companies are currently using cloud data, the importance and power of using data, what the future of cloud data looks like. In addition, Arthur describes a day in the life of a software engineer and provides an honest take on his experience working at a high-growth startup through an IPO

Tune in to this episode to hear Arthur talk more about Snowflake, cloud data, startups, and software engineering.

Matthew Gould is the Founder and CEO of Unstoppable Domains, an innovative startup that builds domain names on the blockchain and sells them to customers for a one-time fee.

In this episode, Matthew takes listeners through the ins and outs of what blockchain and decentralization are, and he dives into blockchain’s revolutionary potential. He shares that one day, blockchain could allow everyone to have a single, cohesive digital identity, ownership over their online experience and data, and overall, greater online transparency and data verification.

Tune in to hear Matthew talk about why it’s important to own your digital assets, how cryptocurrency could disrupt the economy, what the future of blockchain looks like, and more.

“Talent is everywhere; opportunity is not.”

That’s why Andrew Hutton created Day One, an accelerator for early stage startups. He believes that entrepreneurship is going to be the most important skill of the 21st century and wants to make it accessible to more than just the 1% who know how to play the game.

Tune in to hear Andrew talk about what it was like to start a business at the start of the pandemic, what he learned from working at a VC firm, and how he started his career as a pig farmer in Africa.

When most people think about SEO, they still automatically think about keywords. But the truth is, there is so much more to SEO than just keywords.

Ryo Chiba, Founder of Topic, talks about how to take advantage of the ever-changing Google algorithms to create impactful content that ranks highly on Google. With Topic, you can create better content faster.

Tune in to hear Ryo talk about the technology behind Topic, the lucky break he credits for making Topic a success, and his projections for the future of content and SEO.

Work smarter, not harder.

That’s what Ashutosh Priyadarshy, Founder of Sunsama, helps the world’s most successful professionals do each day with his daily planner that organizes everything you need to do today in one place: tasks, meetings, emails, you name it.

Like many entrepreneurs, Ashutosh’s startup journey was not a linear one. In the first 4.5 years after founding Sunsama, Ashutosh and his co-founder, Travis, launched, iterated on, and sunsetted six different products in the meeting, collaboration, and productivity space. Now, seven years later, they’ve finally found product fit and feel confident about the product they have, in big part thanks to their time at Y Combinator.

Tune in to hear Ashutosh talk about how and why he stuck with his long journey toward building the Sunsama we know today, what he learned along the way, and what he’s working on for the future.

Can you really use data and AI to solve social justice issues like racism and do good for the world?

Andrew Ehrenberg thinks so. As a data scientist at DataRobot, Andrew works day in and day out with massive data dumps to build models and make predictions for the owners of that data. DataRobot has essentially operationalized the best practices of world class data scientists and machine learning engineers to help organizations turn their data (questions) into predictions (answers).

Andrew’s work at DataRobot has inspired him to think big and imagine other applications of data science and automated machine learning to create a larger impact in our world.

If you’ve ever contacted customer support for help with an issue with a product or service you purchased from them, you know that high quality customer service is harder to come by than one might think.

That’s why Jim Coleman founded xFusion, which provides customer support for SaaS companies and startups. In addition to providing phone and live chat support, xFusion also provides back end support, like tech migrations and billing support.

Tune in to hear how Jim handled leaving a full time job during the pandemic while raising five kids to build xFusion, some of his best marketing strategies for acquiring his first customers, and why he thinks “relationships over revenue” is the most important philosophy for a founder to live by.

Having just celebrated its 10 year anniversary, Magnitech isn’t technically a startup anymore but still very much operates like one. Much of that startup mentality can be attributed to Magnitech’s CEO and Founder, Tim Pabich, who believes in identifying unique strengths in each of his team members and empowering each person to do the work that truly fulfills them.

Magnitech is an IT managed services provider (“MSP”) - or, in simpler terms, an outsourced IT department for small and mid-sized companies. They provide the whole suite of services - a full blown service desk, project management, cyber security, disaster recovery, and pretty much anything an IT department would provide for a business.

Tune in to hear how Tim got his start in entrepreneurship, how he managed to build and scale a company over a decade, his best advice for newer founders, and his predictions for future changes in technology that will affect the way businesses operate.

Inspired by her auntie, a first generation immigrant who worked hard to send money back home to the Philippines, only to have to pay a whole month’s worth of salary every year in transaction fees, Rebecca Kersch knew there had to be a better way. That’s why she founded TANG App, a payment platform that lets anyone from the US (or other countries) send money and phone credit (a new addition in response to Covid-19) to the Philippines, and eventually to the whole world. Think: a global Venmo.

Rebecca shares about how she built TANG App, from facing tons of rejection to finally finding her tribe to building her team and now growing the business while staying super involved on the ground. She has an attitude that no task is too small for her, despite being the Founder and CEO of the company, and she genuinely cares about connecting with and listening to each and every customer.

She also shares about her personal background of being a Dutch-Filipina who grew up mostly in the Netherlands and how that has impacted her journey toward entrepreneurship.

Tune in to hear all this and more in a fast-paced and fun episode!

You’ve heard from a number of exciting startups on this show, but today we’re diving into the other side of startup world: venture capital.

Brad Baum joins us to talk about the inner workings of VC life, what his day to day as an investor at Lightbank looks like, what investors look for in startups, and much more.

Lightbank is an early stage venture capital firm based in Chicago that has big names like Fiverr and Udemy in its portfolio.

Tune in to hear more of Brad’s story from taking a gap year before college to work on his own startup in Los Angeles to starting his own venture capital firm while attending University of Michigan to getting a job at a notable venture capital firm right out of college -- and find out what he would do differently if he could go back in time.

Reducing inefficiencies is every entrepreneur’s goal, but Jay Hsueh, Founder and CEO at Roby, has managed to solve an inefficiency that has plagued corporate offices for decades.

Roby helps companies streamline their help desk support tasks, like scheduling meetings, managing meeting rooms, controlling office temperature, and more so that all members on the team can work more efficiently and effectively.

This has been an interesting time for Jay as he has had to pivot with the environment, as more and more companies are shifting toward a fully remote or hybrid work setting. Luckily, Jay is “addicted to challenges” (his words, not mine) and already has some exciting new plans for Roby in place.

Tune in to hear more about the future of Roby, as well as Jay’s startup story, from working as an engineer in Taiwan to experiencing corporate life in the U.S. to finally discovering his passion for entrepreneurship. Jay’s positive attitude is infectious, so if you’re looking for something to smile about today, make sure you check out this episode.

You can contact Jay by email at jay@tellroby.com (let him know you found him through the Startup Happy Hour podcast), and don’t forget to check out Roby at the link below!

Happy (almost) Thanksgiving! In this special episode, Diana reflects on what she’s grateful for: diversity in startups and having had the opportunity to have guests on from a wide array of backgrounds.

In this episode, she revisits five of her best conversations with guests about diversity in startups - from gender to race to ethnicity to social upbringing.

If you like what you hear in these clips, don’t forget to go back and listen to the whole episode. Here they are in the order in which they appear:

It’s not everyday you meet someone who holds a PhD and is a startup founder, but it’s not everyday you meet someone like Kat Houghton. After working with children and parents of children with autism for close to a decade while earning her PhD, Kat saw an opportunity to apply technology to psychology and founded ilumivu.

ilumivu offers mobile, web and wearable systems that engage participants in continuous behavioral monitoring and offer a channel for just-in-time adaptive interventions.

Tune in to learn more about how ilumivu helps mental health patients and the biggest lessons Kat learned in the last 11+ years as co-founder and CEO of a startup.

Every startup story contains some mistakes and iterations, but some more than others. Tyler Winn is proof that slow and steady can win the race, even in the startup world.

While the company Tyler first started isn’t the exact same company Cirrus Payroll is today, his regimented and thoughtful approach to entrepreneurship certainly contributed to the stability he sees in his business today.

After attempting to replicate the accounting firm model, he recognized a gap in the marketplace and figured out a way to turn that gap into an opportunity.

Tune in to hear Tyler’s story of what led him to start his own company, his humble journey toward success, and his biggest piece of advice for aspiring entrepreneurs.

With all the fake news and skewed media we’re being fed these days, it’s only fitting that on Election Day 2020 we get to hear from Arjun Moorthy, CEO and Co-Founder at The Factual, which provides unbiased news on trending topics, like the election.

The Factual uses a custom algorithm to evaluate news articles and rate each article’s level of trustworthiness based on a number of factors like diversity of sources, factual tone of writing, author’s expertise, and more.

Tune in to hear Arjun’s story of how he’s always been passionate about news - starting from when he was a paper delivery boy as a kid to how he got the idea for The Factual and actually built it. Stay tuned until the end to hear his biggest piece of advice for aspiring entrepreneurs - it’s unlike anything you’ve heard in previous episodes.

They say not to mix business with family, but what do “they” know anyway? Mother-daughter duo Heidi and Tori Ganahl are not only rocking their business as co-founders of SheFactor but also inspiring and changing the lives of so many young women in their 20s and 30s.

While Heidi (the mom) has always had an entrepreneurial bug, Tori (the daughter) joined this venture purely out of a need she saw in the space with young people - especially women - graduating college with little direction as to a career path and subsequently dragging through careers and jobs that don’t fulfill them.

It’s not easy for most entrepreneurs to admit they don’t have that innate entrepreneurial bug, but Oleksandr Perelotov has no problem talking about it.

Oleksandr started Excited Agency about two years ago not because he was passionate about business but because he was passionate about creating high quality designs for other businesses.

You won’t have to listen long to hear Oleksandr’s passion for design, but you’ll want to tune in for the entire episode to hear about the journey Oleksandr took to get here and his best advice/inspiration for aspiring designers.

Until recently, if you wanted custom made clothing, you’d have to go to a tailor or a high end shop and pay tons of money. When you think about it, that’s a huge hassle and high price tag to just get clothes that fit… is that really so much to ask for??

Mark Zheng says no - everyone deserves to have clothes that fit without going through so much trouble and emptying their wallets. And yes, that’s including people who don’t have the exact measurements you find in sizing charts online.

That’s why he founded Sene, a custom clothing company that uses a top secret SmartFit algorithm to determine your ideal fit without ever having to bust out the measuring tape.

Sene is on a mission to empower people of all shapes and sizes to feel their best - and they’re doing a darn good job of it so far.

Unlike most PhD candidates who dream of teaching at a prestigious university, Aditya Nagrath dreamt of creating a solution to a problem that so many kids in our country face: math.

Over the last 4+ years, Aditya has been helping kids learn math a different way - an easier and more effective way - with Elephant Learning.

After working as a software developer for a number of years, Aditya knew he had to go out on his own in order to make the kind of impact he knew he was capable of making. And so he did.

Using only 10 minutes per day of a student’s time, Elephant Learning guarantees that a student will learn one year of math in only three months.

How can they so confidently make such a guarantee? Tune in to find out.

Despite having founded Undock only two years ago, Nash Ahmed had been brewing the idea in his head for nearly a decade. Undock helps companies instantly schedule, host, and document meetings, and it’s on track to make an even larger impact in the world of remote work.

After going through Startup School at Y Combinator and putting Undock through an accelerator program, Nash got a clear vision for Undock and was able to build it to the product it is today.

In addition to sharing about Undock and his path to entrepreneurship, Nash also opens up about his experiences as a BIPOC in a white male dominated industry.

Stay tuned until the end to hear Nash’s biggest piece of advice for young entrepreneurs, no matter which path they want to take with their business.

Cynthia Del’Aria learned to code at age 8, built her first company at age 15, sold her first company to a major competitor at age 19, built four more successful tech startups, and now runs Raika Technologies, an incubator for new tech startups.

As if that weren’t impressive enough, she did all of that through her own determination and willpower, vowing to leave behind the trailer park life she once knew as a child and build a better life for herself.

In addition to helping new entrepreneurs validate and build out their business ideas, Cynthia also coaches women and other gender minorities to stand tall in their authentic selves and succeed in the male-dominated tech space.

Stay tuned until the end to learn about who Cynthia is outside of work - and the shocking hobbies and accomplishments she’s earned in her personal life.

In this episode, Diana gets to chat with her first CX guest, Robin Marcenac. Robin is the Head of Customer Experience and Success at Pypestream, a conversational AI platform that makes chatbots sound more human.

Diana and Robin nerd out over natural language processing (NLP), how far it’s come since its inception, and how companies like Pypestream use it today.

Robin then shares about what a career in CX looks like and the less than linear path he took to get here. He also takes us through his transition from working at IBM, a large corporation, to working at Pypestream only a couple of years after it was founded.

Stay tuned until the end to learn some surprising facts about Robin, including his birthplace outside of the country, and to hear Robin’s top 3 tips for getting to where he is today.

Originally hailing from Australia, Sasha Pilch found startup paradise in the U.S. when she visited New York City three years ago, and she hasn’t left since. She currently heads new business at Ramp and runs NYC Fintech Women with her co-founder, Michelle Tran.

What started as a way to build Sasha’s own network of fintech contacts in NYC has turned into a community of 5,000+ women (and men!) who are passionate about supporting women in fintech. Sasha and Diana talk about the importance of male allyship in achieving equality in a heavily male-dominated space.

While many people think sales is about the hustle and grind and that “a good salesperson can sell anything to anyone,” Sasha has a different take.

Tune in to hear her advice for salespeople and for women in tech, and to hear the gutsy story of how she turned her back to 10 years of working at big banks to work at a startup company in a foreign country.

In this episode, Diana chats with another fellow Chicagoan, Marc Summe. Marc is the CEO at Minute7, a time and expense tracking software that helps streamline billing for lawyers, engineers, and other professional services providers.

Marc talks about what led him to leave corporate life for the startup world, and ultimately what led him to start his own company. He also introduces Diana to the sport of paddle tennis, which she has never heard of despite its existence in the world for over a century.

In this episode, Diana chats with a fellow Chicagoan, James McGuinness. James moved to Chicago from the UK nine years ago and is now the co-founder of PondLeap, along with his wife.

PondLeap connects overseas companies with freelance salespeople in the U.S. to help overseas companies expand their global reach into the U.S. After holding onto his idea for PondLeap since 2012, James finally decided to take the plunge recently and build out the platform.

James also talks about what (or who) brought him over to the US nine years ago, what he misses about the UK, what it’s like co-owning a business with his wife, and his work superpower.

In this episode, Diana reconnects with one of her former VAs, Jaclyn Curtis, who is now the COO at multiple startup companies.

Jaclyn fills Diana in on how she’s managed to rise through the ranks from VA to Account Manager to COO over the last few years, while introducing another child into the world.

Today, Jaclyn is the COO at two startup companies, Bant.io and Zopto, while raising three young boys at home. She even divulges at the end which child is her favorite (at the moment), so make sure you stay tuned until then to find out.

In this episode, Diana chats with Founder and CEO of Moxie Mouth, Meggie Abendschein.

Moxie Mouth is a social justice consulting agency dedicated to flipping the script on social impact and designing strategies outside of the traditional philanthropic box. While Meggie’s work is focused on the four areas of (1) women, (2) children, (3) mental health, and (4) antiracism, much of her work recently - in light of the resurgence of the BLM movement in our country - has been focused on antiracism efforts.

Meggie shares her story of growing up in the typical Southern home with conservative and religious (Baptist) ideals to learning to form her own belief system in college to mustering up the courage to publicly stand up for what she believes (at the expense of alienating many of her close connections) when she founded Moxie Mouth. She also talks about what it’s like being a female in a male-dominated industry and offers her advice to other women looking to start their own companies - especially those in the nonprofit world and/or centered on social justice issues.

Listen until the end to find out what Meggie’s offering to all women listening and where Moxie Mouth is headed in the future!

In this episode, Diana gets to chat with the first Product Manager she’s had on the podcast!

David Silverman got a job as a Technical Product Manager right out of college and spills the tea on what the elusive PM job title actually means.

Even though his background is in coding and computer science, David is also acutely aware of the less technical sides to building a product, such as customer experience. He shares how he has been able to develop such a well-rounded perspective on building out a product and his best tips for aspiring PMs to do the same.

In this episode, Diana sits down with another client of hers, Teja Yenamandra, to chat about his company, Gun.io. Gun.io is an online platform that helps businesses find and hire elite freelance software developers at a moment’s notice and is used by companies like Tesla, CISCO, and NBC.

Teja shares about his unique startup journey, which started in China. After working for free there, thinking he was going to go to law school, and experiencing life as a dark-skinned man in a society that’s not used to seeing people who look like him, Teja found his passion for startups and moved back to the U.S. to start Gun.io, which is still running strong seven years later.

You’ll want to stick around until the end of this episode to hear Teja’s holistic approach to entrepreneurship, which is focused on mind, body, and spirit - something not many startup founders talk about.

After finding himself closer to the World Trade Center on 9/11 than he would’ve liked and having an existential crisis about what he was doing with his life, Ledge quit his cushy management consulting job and went out on his own.

Over the last 20 or so years, Ledge has been involved in running 13 businesses, so I think it’s safe to say he knows a thing or two about running a business.

In one of the most advice-rich episodes yet, Ledge dishes on all the lessons he’s learned over the years that have led him to run Add1Zero the way he runs it today - with only the ideal clients he wants to work with.

Listen til the end to hear Ledge’s biggest piece of advice for people starting out in the startup world today - it’s probably not what you’d expect.

Startup growth expert, Lisa Han, joins us to talk about how she’s been working hard toward reinventing regulated industries like fintech and legal with companies like Atrium, Ramp, and Instabase. 

Despite growing up with a parent in tech, she never got inspired to get into tech until meeting a group of Thiel Fellows in college. 

Tune in to hear about how she’s tackled strategy, partnership, and growth for startups on the East and West Coasts and what her experience has been being a racial and gender minority in a predominantly male-dominated field.