Bootstrapped Web

By Bootstrapped Web

Brian Casel (@casjam) and Jordan Gal (@jordangal) share their raw and real behind-the-scenes of their entrepreneur journeys. From bootstrapping software startups to raising money to selling and exiti... more

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5858 ratings

FAQs about Bootstrapped Web:

How many episodes does Bootstrapped Web have?

The podcast currently has 379 episodes available.

Bootstrapped Web episodes:

June 25, 2020Heyyy + People-ing, Building & Marketing
We’re back and we have so much to talk about. First off, we’d like to dedicate this episode to Ian Landsman and his twitter account. “Hey” seems to have taken Twitter by storm. We’ll talk about how we feel about that, and, of course, we’ll update you on what’s going on in our businesses as well.
[tweetthis]"For an everyday email app, I need it to be as clean and simple as possible. But the experience and the functionality and the UI makes a lot of sense, I think." - Brian, on Hey from Basecamp [/tweetthis]
Here are today’s conversation points:
Hey (from Basecamp): the pros & cons, and the controversy with the Apple Store
Hiring at Carthook
Recruiters
People Ops person
Culture and training
Onboarding updates at ProcessKit
To build or to market, that is the question
Forms features
Marketing tasks on my to-do list
[tweetthis]“Now we have 8 completely new people we’ve never met, we probably won’t be able to see for, like, a year. How do we give them a good experience? How do we make sure they don’t feel isolated?” - Jordan, on hiring new team members during COVID [/tweetthis]
Resources/Links:
HEY - Email at its best, new from Basecamp
Help Scout - Simple Customer Service Software and Education
Dynamite Jobs
Substack
SunriseKPI
Productize
Audience Ops
ProcessKit
Carthook
As always, thanks for tuning in. Head here to leave a review on iTunes.
...more
1h
June 18, 2020SaaS Onboarding & Recruiting at Scale
We’re back behind the mic today after a one-week hiatus. We had originally recorded an episode last week (which addressed current events) but decided not to publish it. Our hearts do go out to everyone in this time of chaos and uncertainty.
This week, we’re back, talking about business, bad habits, and kindergarten graduation parades. We’re talking about ProcessKit’s onboarding updates and one of their newest customers. We’re also talking about Jordan’s big problem and his recruiting and hiring issues.
[tweetthis]"He turned the tables on me and we bartered. So he’s a paying customer of ProcessKit and I gave him a pretty big ProcessKit plan in exchange for him writing three of these pages for ProcessKit." - Brian [/tweetthis]
Here are today’s conversation points:
Jordan’s big problem: putting off strategic tasks, but then having no energy
Brian’s early morning exercise schedule
Brian’s ProcessKit’s onboarding updates
The various levels of customers
Tools, widgets, checklists, and onboarding courses
What each customer needs in order to be successful
Jordan’s recruiting and hiring process
Their first (in a long time) fully remote hire
Brian’s newest customer experience
What to do with B2B SaaS these days?
E-commerce platform issues
[tweetthis]"The mistakes in hiring are more costly than any monetary mistake. Like, buying the wrong thing, using the wrong software, hiring the wrong consultant. I see those as monetary mistakes. When you making a hiring mistake, it hurts so much more.” - Jordan [/tweetthis]
Resources/Links:
SunriseKPI
Productize
Audience Ops
ProcessKit
Carthook
As always, thanks for tuning in. Head here to leave a review on iTunes.
...more
43min
June 04, 2020Navigating Stress & Distractions
The world is in chaos but we’re still here. Today we’re talking about some of the trends and the future of podcasting after some big news with The Joe Rogan Experience. We’re also going over some updates with Carthook, ProcessKit, and Audience Ops.
[tweetthis]"It does seem like there’s still that massive gap between the seed rounds and the Series A. Right? When you’ve grown to a certain level and you still need more firepower to grow." - Brian [/tweetthis]
Here are today’s conversation points:
The big debate over Joe Rogan’s Spotify deal
Jordan’s (who is not soliciting for investments, SCC) fears over investors
ProcessKit’s onboarding course, not quite ready
Funding: social media ads, marketing partnerships (affiliates and referrals)
Jordan’s biggest deal ever...and he didn’t even talk to the prospect
Difficult clients in Audience Ops
[tweetthis]"You’ve been working on something for over five years. This is all you care about. You love it. You love the job, the company, the people. There’s so much involved in that. How are you supposed to find investors that are going to respect that?” - Jordan [/tweetthis]
Resources/Links:
Substack
SunriseKPI
Productize
Audience Ops
ProcessKit
Carthook
As always, thanks for tuning in. Head here to leave a review on iTunes.
...more
45min
May 28, 2020What if we take some off the table?
In today’s episode we’re talking about socializing with family friends and work during the pandemic, as well as the latest news and questions on our minds about the current status of tech and the world. PokerStars, weekly stand-ups, Facebook, and what reopening might look like. The big question on everyone’s mind is: “How long is this going to last?” In business news, we’re talking about Brian’s new ProcessKit course, and Jordan’s views on hiring.
[tweetthis]"You’re taking money off the table but you’re also taking off the table, the desire to sell when the first semi-big offer comes along and instead go super-big." - Brian [/tweetthis]
Here are today’s conversation points:
Facebook news
Jordan’s most popular tweet ever
Taking on more money and the possibility of hitting zero
What is Clubhouse and why is it so big right now?
Serendipitous audio conversations versus Twitter versus podcasting
Private podcasts
Interesting new platforms: Substack
Updates on Brian’s new course about ProcessKit
Jordan’s views on hiring
Brian’s work on the sales demos
[tweetthis]"People watch how you treat people and then they put themselves in those shoes.” - Jordan [/tweetthis]
Resources/Links:
Clubhouse.io
Substack
SunriseKPI
Productize
Audience Ops
ProcessKit
Carthook
...more
42min
May 21, 2020Managing Customers & Managing Teams
Welcome back! Brian and Jordan are back behind the mic. We’re talking about ProcessKit’s best month, and Brian’s excitement about moving forward and making progress. We’re also talking about Jordan’s experience with Carthook’s people coach and accidental faux pas with his leadership team.
[tweetthis]"I am acting fast on a lot of the smaller requests. I only do it when I’ve heard it two or three times from different customers. Usually and hopefully I’m shipping something fast and notifying multiple customers that, ‘Hey, we just shipped that thing." - Brian [/tweetthis]
Here are today’s conversation points:
ProcessKit’s best month with conversions
Jordan’s focus on hiring and salaries
Brian’s focus for ProcessKit: onboarding
Brian’s old blog posts
Setting up SEO
Jordan’s humbling experience with the people coach
Accidentally taking away authority
Brian’s support requests on ProcessKit
[tweetthis]"What am I really doing though? I’m taking authority away from their manager. I’m not allowing that manager to be that person, resource, and that trust and that bond and… I’m messing with that and it’s not helpful." - Jordan [/tweetthis]
Resources/Links:
Ahrefs.com
SunriseKPI
Productize
Audience Ops
ProcessKit
Carthook
As always, thanks for tuning in. Head here to leave a review on iTunes.
...more
45min
May 14, 2020 Remotely Working on Working Remotely
We’re back for another episode of Bootstrapped Web. This episode is all about our thoughts on quarantine hair, having our kids at home, and working from home challenges. We’re talking about how to make working-from-home better, happier, and more productive. This week’s ad is for Council.Club, which is an invite-only site that helps remote workers … Continue reading Remotely Working on Working Remotely
...more
41min
May 05, 2020 Trailer: The Productize Podcast returns in 2020
Brian shares a quick announcement for his other podcast, The Productize Podcast. That’s an interview show where Brian invites business owners who are scaling with systems, processes, and teams — Primarily those in productized services, but he also speaks to SaaS founders who are pairing services with their software. It’s a different format than Bootstrapped … Continue reading Trailer: The Productize Podcast returns in 2020
...more
3min
April 30, 2020 Raising Our Game
We’re back behind the mic and keeping the streak going during the quarantine. Today we’re updating each other on our energy levels on Day # Who-Knows-What of “quarantine life”, catching up on the latest news in our businesses, how we put pressure on ourselves, road maps, standards & communication, Shopify crises, and “sponsored ads.” Not … Continue reading Raising Our Game
...more
49min
April 23, 2020 People and Process
Most of us are hovering around week 5 of the quarantine. How are you holding up? Today we’re talking about the lack of barbers and salons, the state of the economy, trends in our businesses and what we’ve seen in the market, the latest news on Carta, and updates on our businesses. We also address … Continue reading People and Process
...more
44min
April 16, 2020 Scrambled
This is four weeks in a row now. Quarantine life is conducive to podcasting. Coronavirus has put people into precarious positions right now. What should be on our priority lists? How do you handle traumatic or dramatic events during a global crisis like Coronavirus? Especially while we’re all working remotely. Today we’re talking about what’s … Continue reading Scrambled
...more
48min

FAQs about Bootstrapped Web:

How many episodes does Bootstrapped Web have?

The podcast currently has 379 episodes available.

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Bootstrapped Web

FAQs about Bootstrapped Web:

How many episodes does Bootstrapped Web have?

Bootstrapped Web episodes:

FAQs about Bootstrapped Web:

How many episodes does Bootstrapped Web have?

More shows like Bootstrapped Web

Startups For the Rest of Us

MicroConf On Air