Startup Therapy

In today’s Startup Therapy Podcast, Wil and Ryan talk about what happens when funding is scarce. Will you seek another investor? Will you go on a fire sale? What other options do you have left? In the world of Startups and the struggles of keeping your business running, the fight is for you not to win. It’s more of a fight for you not to lose! 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 What do we do when no one wants to give us money 02:04 Is there a heads up when you’re not getting additional funding? 10:33 First, admit that you’re f*cked 16:00 Next, you go on a fire sale 22:13 Investors won’t get their money back but they wont lose more  25:51 What are your remaining options? 28:32 We’re playing not to win, but not to lose

In today’s Startup Therapy Podcast, Wil and Ryan talk about celebrating the little successes. Most people focus on hiring more people, settling in a bigger office, or getting additional funding as a form of success. But for most founders, at the early stages of their business, smaller things such as not having to worry about the payroll or how much you can spend using the company card, are a little form of success. It’s about taking away liabilities one at a time. 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 00:14 Misconceptions about success 06:02 When you no longer worry about payrolls 10:01 Happiness and success comes from taking things away  16:28 At the early stage, it’s always close to the line 20:59 Chipping away the little liabilities over time 22:42 Focus on the moments of little success 27:11 We are rewar

In today’s Startup Therapy Podcast, Wil and Ryan talk about when is the best time to give up equity. At the early stages of a Startup, founders often seek to partner with a co-founder in the hopes of growing the company. But what founders don’t realize is that it may be too early to look for a partner or too risky to look for one. Selling the equity of your company, when it’s at its lowest value, will only nip down its potential growth.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 00:14 When is the wrong time to raise a capital? 04:02 The equity is future value of your company 09:29 Is giving up equity the only way? 17:27 The single most expensive investment: meeting your co-founder 20:24 The story of two founders 23:56 What if there’s a law that won’t allow a co-founder in the first year 25:02 Another founder story

In today’s Startup Therapy Podcast, Wil and Ryan talk about rising from a failure. Founders take it to heart when their business fails and often think that people will remember them for their failed business. Fact is, people easily move on and forget about the failed business. They won’t care. So, wallow on it as much as you want and then move on. A founder’s path is always open to more job opportunities. 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 00:37 How paralyzing failure can be 04:39 Let’s talk about what losing it all feels like 09:14 When the business goes bankrupt, is your career completely over? 16:15 You’re still around, what do you do next? 20:22 When you think everyone will care all the time 24:01 Founder path lead to more job opportunities

In today’s Startup Therapy Podcast, Wil and Ryan talk about taking a break to restart. The biggest fear founders have is what happens to the business when they take a much needed break. The fear that things might go wrong, the right decisions aren’t being made, or there’s simply too much to do that taking a break may sound hilarious. But guess what, with the right people in place, more than half of a founder’s work can be done by someone else. 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 00:29 We don’t believe we are allowed a sabbatical time off 05:25 You’re burned out but you can’t detach yourself from the business 09:37 Founder sabbatical is going away and doing something else entirely 14:09 You should be able to reset and come back with a fresh head 18:55 A sabbatical break has to happen 22:37 Setting the time

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

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 ab

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 in

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

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 sala

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 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

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

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 contribut

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

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 succes

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

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

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 ov

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