In today’s Startup Therapy Podcast, Wil and Ryan talk about honest optimism. What if you have this strong conviction that what you’re building will lead to success? What if you have this strong sense of positivity and optimism? Will it be enough to gain people’s trust and continue to pour more money into your company? But what if it’s just blind optimism and you’re not really getting anywhere? Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:22 Forward-looking optimism versus lying 03:28 Are we lying to ourselves when outcomes aren’t as predicted?   06:42 What we’re pitching is potential outcome 09:56 Reasonable expectation and not blind optimism 12:08 Understanding the importance of optimism 18:44 Here’s where it becomes straight up lying 22:28 The consequence of going beyond optimism 26:43 Founders getting caught up in not presenting 28:38 There’s truth in optimism and there’s misaligned intention 

Startup Therapy

Am I Lying or Just Being Optimistic?

In today’s Startup Therapy Podcast, Wil and Ryan talk about the 100-hour work week. The adrenaline to overexert and overwork yourself so you can get more things done is a hustle that no founder should be investing into. Here’s why. You can only get things done at your peak hours. No one gets productive a hundred hours a week. It’s an awful burnout.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:45 The Hustle Porn hype: The 100-hours work week 05:21 How many hours a day are your peak hours? 09:25 If you give yourself more hours, you spend more hours 13:15 Why are your work days loaded? 18:54 When you think you’re crushing it 22:30 Oh, you’re crushing it but at what cost? 28:02 The 30-second success story of a founder on social media 31:19 Get out of the habit of ‘how you’re crushing it’ 32:28 Those who don’t brag about crushing it are actually the ones getting the work done 35:55 We need to put an end to the hustle porn 

Stop Glorifying "Hustle Porn"

In today’s Startup Therapy Podcast, Wil and Ryan talk about a founder’s social circle. Wherever you may be, you’ll always meet another founder. Surprisingly, your Startup is helping you build these connections, a space where you can meet and create relationships with people who share the same experience as you and probably have similar views as well. A founder’s space is just the right place to check how far your voice can influence and be heard.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:46 Startups are the social engines for most founders 03:07 Your social circle evaporates when you sell your company 07:37 Our relationships often have consequences 11:39 Understand which relationships are worth maintaining 15:12 Startups create a magnet for interesting people to join your circle 21:12 How far your voice can influence and carry 26:12 What we do creates a social gravity 29:41 Diversity in the founder’s space 

Startups Actually Amplify our Social Lives

In today’s Startup Therapy Podcast, Wil and Ryan talk about being the best at what you do. Oftentimes, founders are stuck in the idea that they need to add more features to make their product appealing and saleable. That it’s the added features that will reel in more customers without realizing that the focus should be on the core value of their product - to make sure that we’re doing the core product right and nothing else matters.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:20 We’re lucky if we’re really good at one thing 03:11 If you can’t solve the primary problem, you can’t fix anything else 06:10 What’s the one thing that you’ll have room to add features? 11:06 The cost of doing anything but the one thing 15:28 Nothing matters when you can’t get the core product right 19:26 If your mission is pizza, stick to it 24:01 We’re always going for a market we have to condition 30:59 Being the first to a market doesn’t make you the best 36:45 It’s difficult to beat the best when you’re new in the market 

We Only Get to be Great at One Thing

In today’s Startup Therapy Podcast, Wil and Ryan talk about moving to a major city. Years ago, when a business needed to expand, they often moved to a big city, brought key employees in, and raised funding to cope with a much higher cost of living. But times have changed. A lot of founders can now settle anywhere without the need to drag their employees and their families around. Remote setup is the new normal, and it’s giving Startups the advantage of growing without emptying the bank.  Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:25 Everyone started leaving the mega cities 03:32 When you leave a major city and start your business somewhere else 06:16 An expensive city is a liability 12:14 You raise funds just so you can work within a geographic constraints 17:20 Hiring someone elsewhere for a much cheaper salary 23:37 Most people don’t necessarily want to live in an expensive city 28:19 Founders can move around and have the rest of the team settled anywhere else 31:46 Does your team need to be where you are at? 34:36 You can still show up in places when required 39:32 At this point, you don’t have to live in a major city  

Flee Your Overpriced City

In today’s Startup Therapy Podcast, Wil and Ryan talk about optimism. An optimistic leader creates an optimistic environment. Despite the onslaught of negativities and failures, and success seemingly slipping away, when a Founder remains optimistic, he can always redirect his focus on what to do next.  Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:24 Blinded optimism keeps founders running 04:49 Whatever you do will be reflected throughout the organization 08:19 Founders do not have the luxury to cry over spilled milk 10:01 Distraction keeps us away from being successful 12:37 You can’t find a customer or investor in one seating 15:51 Focus on small tiny wins that build success 19:16 Building a Startup through optimism 21:32 Optimism should be left in the hands of fate 

In Our Darkest Hour, Where Do We Find Hope?

In today’s Startup Therapy Podcast, Wil and Ryan talk about dumb ideas. It’s no surprise that most of the successful Startups today started off as a completely bad idea. As it turns out, when given the time to evolve, the market to mature, and the target audience to be open about it, the dumbest idea can become the most profitable company.  Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:36 How many successful Startups started as a great idea? 04:26 Founders are stuck in “my idea needs to be better” 06:07 Ideas are a process and it can change a thousand times 09:24 Why is it called Netflix? 11:46 The market matures and the idea matures, we have to give it time 13:07 This concept that the development of an idea is a linear process 16:04 There aren’t a lot of people willing to invest in Startups 

Great Ideas Start as Dumb Ideas

In today’s Startup Therapy Podcast, Wil and Ryan talk about how some founders can’t flaunt their money. Founders worked for it, sacrificed their health and time, and at some point, even settled for less compensation for the company to grow. They earned it, and yet some people find it appalling just because they don’t have it.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:46 Why is everybody counting our money? 06:09 The fact that they can’t have as much as you have pisses them off 09:17 The compensation gap will continue to increase 10:58 No one will appreciate your years of service 14:14 What people see and what the reality is are too different 19:22 You should not be ashamed of what you’ve earned 20:59 How you present your success can change the perception 25:15 Laylow in all of your personal stuff, don’t expose it 28:19 Is it an indication that things are doing better? 

Why Is Everyone Counting My Money?

In today’s Startup Therapy Podcast, Wil and Ryan talk about what happens when you leave your Startup. You can’t simply assume that you’ll still be compensated for the equity without continuously providing value to the company’s growth. It’s a simplified Math problem. If you don’t work, you don’t get paid. If you’re not adding value, you won’t be compensated.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:49 People that are earning but aren't’ present 03:46 The absentee landlord 07:39 Founders didn’t realize they have an option 10:04 Doing the same work with less of an outcome 12:33 Equity is compensation 16:46 How can you get compensated for staying? 20:44 You continue to work to create value for the equity 23:57 You can’t be compensated for life if you leave 28:07 Can’t be compensated daily if you aren’t contributing daily 31:58 You’ve got two options 34:56 Typical when the company is raising money, it’s already running out of money 37:00 Your contribution depreciates as time passes 40:30 The compensation you get when you stay 

Beware of the Absentee Landlord in the Cap Table

In today’s Startup Therapy Podcast, Wil and Ryan talk about the kind of culture you as a founder can create within your own organization. Everything you do has implications and if you let instigators of negativity be, you’re allowing a nasty culture to spread. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 01:25 Where do cultural issues stem from? 04:48 Back channeling is worse in remote settings 08:15 This culture of talking ill about the client 11:13 When KPIs push the retention team to bash the clients 15:20 It all starts with one person, identify the ringleader 18:57 It’s easy to create a culture of overwork 23:35 A lack of maturity across the board 26:30 The spotlight is on you and anything you do has implications 28:50 But you still need to take care of your own well-being 30:52 What company culture meant years ago 33:13 You can admit you made a mistake and create a culture out of it 37:09 Founders can have so much impact, but it can be good or evil 

Startup Culture if a Reflection of its Founders

In today’s Startup Therapy Podcast, Wil and Ryan talk about cofounder breakup. Likened to marriage, having a cofounder requires commitment that comes with consequences when and if the Startup fails and coming up with an action plan when the business turns out to be a total flop. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:33 Cofounders often don’t last 02:07 Cofounders should talk about what to do when things doesn’t work out 05:36 We make a binding contract with someone when the Startup longevity is uncertain 06:57 Founders don’t consider what to do if and when cofounders leave 09:16 Making a commitment at a time we know least about the outcome 14:24 Assumptions you’re making about your cofounder 21:10 Be prepared to deal with fundamentally different decision making 25:48 Plan for divorce but hope for a successful marriage 26:54 Start with a vesting agreement 31:33 Sign a commitment that when not met has consequences 

Why Cofounders Often Don't Last

In today’s Startup Therapy Podcast, Wil and Ryan talk about taking the slow growth approach. Instead of going full force too fast early on, take the time to understand whether the bets you’re paying back or not and when it’s time to change direction. Don’t follow the narrative that you need to accelerate right away. Follow the circumstances and consequences, and move at the pace that you’re supposed to take.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:32 Dispel the myth about Startups should grow fast 01:57 Why do we feel we have to grow fast? 05:56 The car analogy: why early acceleration amplifies mistakes 08:34 The assumption we often miss is the factor of time  12:37 The best you do are the ones that you didn’t do 14:34 When you start to do too many things at the same time 17:30 Don’t mistake making bets into making good decisions 23:06 We get trapped in that repeatability phase 26:24 All the time we waste is a lot of money 29:59 The cost of accelerating the wrong people  

The Case for Growing Slowly

In today’s Startup Therapy Podcast, Wil and Ryan talk about founders rushing into building their next Startup. After a successful exit, most founders are overly eager to start their next big idea and land another win. They want to act upon it while they are in the momentum and prove that they aren’t a one-hit wonder.   Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:36 Is it healthy to jump to the next Startup after you sold the first? 05:06 At some point you’ve already won, don’t rush to the next thing 09:08 Give yourself time to morph into an idea 13:12 The best ideas doesn’t often spring from boredom  17:21 All the best ideas started off small and dumb, but founders don’t think like that 23:03 Stories of founders who succeeded on their second act 27:58 Give yourself time to understand the drive and identify the false motivators  31:11 Take a little time to know the new you post exit  

Don't Rush Into Your Second Act

In today’s Startup Therapy Podcast, Wil and Ryan talk about liquidation probability. Many Startup founders make the wrong decision to lose interest in what they currently have and start pursuing something else in the hopes of a much bigger outcome, completely skipping the part where they first have to gauge the probability of success.  Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:13 You should be more concerned about what you don’t own 05:40 The probability of liquidity is so low 09:06 The probability of your Startup getting liquidated and then liquidating the next 12:52 Important numbers: probability, equity that you own, and the value of equity   17:30 When the money you sold for is sitting on a preference 20:02 Probability should change the likelihood that you would sell  22:55 Always go with probabilities over percentage 26:57 We give up what we have and latch onto something with low probability 32:56 You only have so many years of peak earning potential 

It's not What We Own - It's Whether It's Liquid

In today’s Startup Therapy Podcast, Wil and Ryan talk about opinions that do not matter when a company sells. A lot of founders are stigmatized for selling their Startups for too little. Too little in a sense that these non-founders only think of the numbers and not the value and work put into building the business. And the glaring truth is that they have never had that much money in their entire life! So their opinions aren’t valid.  Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources: Startup Therapy Podcast  https://www.startups.com/begin Join our Network of Top Founders  Send an email to therapy@startups.com  What to Listen For 00:00 Intro 00:53 To those who said, “That founder sold the company for too little.”  05:38 The lack of self-awareness of people making unnecessary comment 09:42 The unsolicited comment will constantly haunt the founder 13:46 Shooting back at the trolls just brings more trolls 17:49 $2M is $2M, how is that bad? 21:31 You can’t belittle $2M if you don’t have it 23:59 People are just chasing more without a clear objective 28:15 If the amount is relative to the founder’s needs, it’s a winning sale 30:00 Not all founders are able to sell their business 35:32 Founders shouldn’t lose sight of their accomplishment 

That Founder Sold for Too Little!

The "No BS" version of how startups are really built, taught by actual startup Founders who have lived through all of it. Hosts Wil Schroter and Ryan Rutan talk candidly about the intense struggles Founders face both personally and professionally as they try to turn their idea into something that will change the world.

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Startup Therapy

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