Startup Therapy

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/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:20 We’re lucky if we’re really good at one thing03:11 If you can’t solve the primary problem, you can’t fix anything else06:10 What’s the one thing that you’ll have room to add features?11:06 The cost of doing anything but the one thing15:28 Nothing matters when you can’t get the core product right19:26 If your mission is pizza, stick to it24:01 We’re always going for a market we have to condition30:59 Being the first to a market doesn’t make you the best36:45 It’s difficult to beat the best when you’re new in the market

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/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:25 Everyone started leaving the mega cities03:32 When you leave a major city and start your business somewhere else06:16 An expensive city is a liability12:14 You raise funds just so you can work within a geographic constraints17:20 Hiring someone elsewhere for a much cheaper salary23:37 Most people don’t necessarily want to live in an expensive city28:19 Founders can move around and have the rest of the team settled anywhere else31:46 Does your team need to be where you are at?34:36 You can still show up in places when required39:32 At this point, you don’t have to live in a major 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/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:24 Blinded optimism keeps founders running04:49 Whatever you do will be reflected throughout the organization08:19 Founders do not have the luxury to cry over spilled milk10:01 Distraction keeps us away from being successful12:37 You can’t find a customer or investor in one seating15:51 Focus on small tiny wins that build success19:16 Building a Startup through optimism21:32 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/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:36 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 times09:24 Why is it called Netflix?11:46 The market matures and the idea matures, we have to give it time13:07 This concept that the development of an idea is a linear process16:04 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/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:46 Why is everybody counting our money?06:09 The fact that they can’t have as much as you have pisses them off09:17 The compensation gap will continue to increase10:58 No one will appreciate your years of service14:14 What people see and what the reality is are too different19:22 You should not be ashamed of what you’ve earned20:59 How you present your success can change the perception25:15 Laylow in all of your personal stuff, don’t expose it28:19 Is it an indication that things are doing better?

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/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:49 People that are earning but aren't’ present03:46 The absentee landlord07:39 Founders didn’t realize they have an option10:04 Doing the same work with less of an outcome12:33 Equity is compensation16:46 How can you get compensated for staying?20:44 You continue to work to create value for the equity23:57 You can’t be compensated for life if you leave28:07 Can’t be compensated daily if you aren’t contributing daily31:58 You’ve got two options34:56 Typical when the company is raising money, it’s already running out of money37:00 Your contribution depreciates as time passes40:30 The compensation you get when you stay

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/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro01:25 Where do cultural issues stem from?04:48 Back channeling is worse in remote settings08:15 This culture of talking ill about the client11:13 When KPIs push the retention team to bash the clients15:20 It all starts with one person, identify the ringleader18:57 It’s easy to create a culture of overwork23:35 A lack of maturity across the board26:30 The spotlight is on you and anything you do has implications28:50 But you still need to take care of your own well-being30:52 What company culture meant years ago33:13 You can admit you made a mistake and create a culture out of it37:09 Founders can have so much impact, but it can be good or evil

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/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:33 Cofounders often don’t last02:07 Cofounders should talk about what to do when things doesn’t work out05:36 We make a binding contract with someone when the Startup longevity is uncertain06:57 Founders don’t consider what to do if and when cofounders leave09:16 Making a commitment at a time we know least about the outcome14:24 Assumptions you’re making about your cofounder21:10 Be prepared to deal with fundamentally different decision making25:48 Plan for divorce but hope for a successful marriage26:54 Start with a vesting agreement31:33 Sign a commitment that when not met has consequences

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/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:32 Dispel the myth about Startups should grow fast01:57 Why do we feel we have to grow fast?05:56 The car analogy: why early acceleration amplifies mistakes08:34 The assumption we often miss is the factor of time 12:37 The best you do are the ones that you didn’t do14:34 When you start to do too many things at the same time17:30 Don’t mistake making bets into making good decisions23:06 We get trapped in that repeatability phase26:24 All the time we waste is a lot of money29:59 The cost of accelerating the wrong people

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/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:36 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 thing09:08 Give yourself time to morph into an idea13:12 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 that23:03 Stories of founders who succeeded on their second act27:58 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

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/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:13 You should be more concerned about what you don’t own05:40 The probability of liquidity is so low09:06 The probability of your Startup getting liquidated and then liquidating the next12:52 Important numbers: probability, equity that you own, and the value of equity 17:30 When the money you sold for is sitting on a preference20:02 Probability should change the likelihood that you would sell 22:55 Always go with probabilities over percentage26:57 We give up what we have and latch onto something with low probability32:56 You only have so many years of peak earning potential

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/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:53 To those who said, “That founder sold the company for too little.” 05:38 The lack of self-awareness of people making unnecessary comment09:42 The unsolicited comment will constantly haunt the founder13:46 Shooting back at the trolls just brings more trolls17:49 $2M is $2M, how is that bad?21:31 You can’t belittle $2M if you don’t have it23:59 People are just chasing more without a clear objective28:15 If the amount is relative to the founder’s needs, it’s a winning sale30:00 Not all founders are able to sell their business35:32 Founders shouldn’t lose sight of their accomplishment

In today’s Startup Therapy Podcast, Wil and Ryan talk about putting every down for a much needed break. No, you can’t say, “I can’t take a break yet.” Or say, “Your hands are tied at the moment.” It’s critical that you take a break in between milestones, unless you want to get stuck on productivity and run dry on creativity. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:24 When will you take a break?05:08 Find milestones to fit in long-term breaks10:37 Founders excel at planning but terrible at taking a break13:41 When your only milestone to take a break is getting sick18:59 If you recharge, you can do more work22:48 The golden periods of creativity and analytical productivity24:10 Get off, reset, and get back on with maximum energy28:40 Some people aren’t taking PTOs32:20 The concept of multiplicity33:52 You’re going to come back as a better version of yourself

In today’s Startup Therapy Podcast, Wil and Ryan talk about focusing on what you are trying to achieve before taking action on any big ideas you might have. Some of these ideas don't necessarily lead you to where you want to go. Some, if pursued, just end up in failures and frustrations. Instead, focus on where you want to go and then figure out how you want to get there. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:24 Getting stuck in looking or working on an idea03:41 Your business idea should align with what you love to do06:46 Aspirations change as we age11:00 Making a business out of something you’re good at17:59 Specific goals makes it easy to map things around it23:05 Every founder knows what to avoid27:21 Just stop doing things that make you unhappy31:29 When you’re using the wrong yardstick to measure growth35:24 How to get paid for what you enjoy doing

In today’s Startup Therapy Podcast, Wil and Ryan talk about how increasing your staff does not necessarily mean growth, but a deliberate liability. Many people just focus on increasing the number of their employees and do not think about the cost of hiring more people. Yes, you need more people to get work done faster. Yes, you need additional minds to pitch in new ideas. But what if your revenue is lower than the liabilities? Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:39 Some people use staff count as a measure of success03:40 A growing staff is only seen as a progress07:01 Management strain continues as you add more people10:48 There’s a diminishing return in every additional hire14:28 Each new person that comes in is a burden in some form16:08 Why do we associate hiring people with growth?20:11 Putting people on payroll is easy, paying the payroll isn’t24:33 Look at every choice as a possible liability26:30 What can we do to keep revenue and stay efficient with staffing? 28:32 Getting additional funding to add people and accelerate things32:13 If the Startup doesn’t work, you’ll regret adding more people

In today’s Startup Therapy Podcast, Wil and Ryan talk about the dues founders pay for neglecting their health. Pushing yourself too much, putting your body through so much pressure, and then ignoring the warning signs as they come, you’re unconsciously trading your life for the success of your company. Don’t curse yourself in the process! Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcast https://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:43 When you’re running your life too fast, you’re sacrificing your health07:50 Processing all of life by not processing it14:26 Because your body can adapt to anything, you shrug off any symptom18:07 Early in our careers, we’re not aware of these problems21:38 Founders rarely have a support structure25:09 We're responsible for the conditions that created the liabilities27:18 It’s difficult to admit you’re wrong when you made the bad decision29:44 A lot of founders have had a massive panic attack at 3732:28 When you’re deteriorating, why aren’t you doing something about it?35:31 Your family can help spot the warning signs, but they won’t be 39:14 At your age, how much stamina do you still have?40:53 How to avoid destroying yourself as your Startup grows43:21 We assume that we’re the only ones going through it

In today’s Startup Therapy Podcast, Wil and Ryan talk about what happens when things work for everyone else but not for you. The effort founders put into our Startup is a sacrifice in all forms and shapes, to the extent of spending less time with family, neglecting our health, or even getting a pay cut just to keep the business rolling. Yes, you are the founder but you’ve become a slave to your own business. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:11 Things are going great for everyone except for you04:20 Concepts that led to you being a founder07:17 We're essentially mortgaging our goals without realizing it12:36 When we take an investor, the investor becomes our boss15:32 You need to set goals that are unchangeable21:24 There is a threshold where commitment becomes destructive26:12 It’s disruptive when you pick up on things your employees didn’t do

In today’s Startup Therapy Podcast, Wil and Ryan talk about changing a person’s personality (or the attempt to do so). It’s one of the factors founders cannot control and it’s silly to keep telling the same person what they should be doing more than once. It’s a waste of energy, a waste of time, and definitely a lost cause. Put your time and effort into someone else!Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:22 Trying to enforce behavioral change in your people04:32 Them being a jerk is just reflection of our bad leadership 08:40 Skills: the things you can do, Personality: the things you can’t do11:59 We keep thinking that we are the solution to the problem16:54 Set an environment with a healthy culture people can mimic20:56 Do not allow performance to outweigh the emotional wellbeing of the business23:03 What would the problem look like if the person isn’t making it worse?27:49 You shouldn’t be telling people to work harder33:39 Ask yourself: Am I parenting or managing?36:35 Personality issues are some of the problems founders can’t control

In today’s Startup Therapy Podcast, Wil and Ryan talk about burnout when you’re nearly at the end of your Startup journey. Every sacrifice and risk you’ve taken will become useless if you feel tired and decide to take a break at the most crucial time and that’s when you’re at the last step of closing the deal. The trick is to surround yourself with people who will help you get through this phase. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:55 What happens when we’re near the end of the deal?05:53 Startup equity is the most expensive currency one can spend09:31 When you just want to be done with it11:56 What else can you do to motivate yourself?17:54 Being vulnerable at this stage doesn’t allow for a second chance20:21 What happens if you fall apart at the last moment?24:53 Every hardship loses value if you drop everything now28:10 There’s no version of a Startup that doesn’t have a burnout32:01 Don’t go through this process alone

In today’s Startup Therapy Podcast, Wil and Ryan talk about avoiding unpleasant breakups. There always comes a time when you need to part ways with people, friends, staff, even investors. Every bad breakup can seriously damage your reputation in any means possible simply because some harbor vindictive emotions and speak negatively against you. What can you do then to avoid that? Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:22 How many good stories do you remember of breakups throughout your career?03:55 Your poor actions is what people remember the most06:21 Letting go of people means having more than one conversation12:42 Your reputation takes years to build and takes seconds to destroy17:23 The damage a single blown relationship can do22:41 How handle breakups that usually end well25:10 The need to justify yourself and your actions28:25 It matters if they don’t feel mistreated when the breakup happens34:04 A little touch can change the tone and reignite a soured relationship38:58 We have to be structured and strategic with our words

In today’s Startup Therapy Podcast, Wil and Ryan talk about what happens after you sell your Startup. Beyond the big paycheck that will certainly make your life better, is the lingering attachment you have for your company and what becomes of it after you give up ownership and control over it. And what about the employees you’re leaving behind? Will they be well taken care of?Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:40 This fantasy of reaching this level when you want to sell your Startup05:35 When you sell, how is everyone else in the organization affected?08:59 From the one making the decisions to asking permission from someone else14:01 Realizing that you have to step off the trail is a tough pill to swallow17:51 It won’t be the same environment and a lot of people won’t stick around23:26 This is about what to consider when you sell26:02 Investors will only see you as a fall-in-line employee32:08 If things were great, why do we want them to end?39:17 It’s not just you, but the employees within the company

In today’s Startup Therapy Podcast, Wil and Ryan talk about power struggle. A lot of us are used to hearing people telling us what we should and shouldn’t do, what we can and cannot achieve just because these people have tried it or have been in a similar situation. What they don’t realize though is the difference in capacity and skills. What works for them may not work for you, and what works for you didn’t work out for them.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:27 The value in having a level of power and control in an agency02:45 When having somebody else determine your destiny wasn't going to work for you11:01 Setting your own path and not allowing anyone to tell you what to do16:36 Stop listening to what everybody else is telling you to do23:31 If you can do it once, you can do it again27:10 What if the investors investing in you aren't what you should be focused on?28:36 Attaining power that wasn’t handed to you gives a sense of inner peace33:43 Set your own terms so other people can set their own37:34 Figure out how to create power for yourself and extend it to the world

In today’s Startup Therapy Podcast, Wil and Ryan talk about regret. Founders are bound to make decisions all the time. These decisions can make or break the Startup, and this is why regret is inevitable. Not all decisions bring a positive outcome, and when the outcome is the opposite of what you had anticipated, it’s part of the risk you’re taking. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:33 Can you remember the first time you felt regret during a trade off?05:15 The regret didn’t kick until later07:43 Many of the risks that we’re putting up won’t return11:39 We assume that we can make up for these risks14:09 Don’t use the same pattern whenever you experience something new17:28 When we form habits, we stop thinking about the different outcomes21:32 Myth: No matter what the sacrifice is, you’ll be able to pay it back in the future25:52 Going on a vacation but not really enjoying the vacation27:25 We have to periodically reassess the sacrifices that we make30:53 Founders are experts at manufacturing anxiety

In today’s Startup Therapy Podcast, Wil and Ryan talk about how we get blinded by the early signs of growth. When things go well, we tend to think it’s the golden moment and that your Startup is on it’s way to getting big, only to find out a week or a month later that you’re back at step one. Early stage successes become dangerous when we get blinded by them and start making the wrong decisions.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:20 Early signals that tend to blind us from what we actually should be doing04:54 It becomes dangerous when we start making decisions based on sudden growth08:41 When things go well, it increases our vulnerability to make the wrong decisions14:23 Yes, it’s going well, but you aren’t making any profit19:24 It’s a mentality problem when we get too excited at the early stages23:43 External signals sometimes send the wrong message27:08 Don’t get blinded how well your product is received after launch

In today’s Startup Therapy Podcast, Wil and Ryan talk about when is the best time to sell your Startup. It’s a tedious process so you shouldn’t just focus on what’s happening during the negotiations but also the pros and cons after the sale is made. And of course, how much you’re being paid for selling is as important as HOW you’re getting paid. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:11 “What happens if I sell too early?”06:36 Buyers are often negotiating to pay for a company’s future value10:17 Whatever cash you’re taking now might be the last cash you’ll ever get in the negotiations15:10 It’s not about how much but HOW you’re getting paid17:58 Myth: The maximum amount the company is worth is equal to how much the founder need27:21 You have to be realistic that you might not be able to sell

In today’s Startup Therapy Podcast, Wil and Ryan talk about going back to an office setting. The idea that more work gets done inside the office is no longer as effective as it used to be. An office setting may not be that substantial anymore for Startups. A lot of businesses are being run remotely and by far, they are progressing well.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:28 What happens when we return to our offices?04:15 In current times, is an office really necessary?08:47 Myth: We need an office to build culture15:59 An office is the least likely way to build friendships23:37 Myth: We need an office to get work done27:20 Office equals work is no longer true30:36 Slack and other project management tools can make collaborations happen35:25 Collaboration versus coordination

In today’s Startup Therapy Podcast, Wil and Ryan talk about the notion that your current success will be the same for every Startup you build. While you’re in the momentum and when new ideas come in, you’re most likely tempted to venture into another Startup. Right? But, take a pause there and consider the odds of your success. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:25 The notion that your current success will be lifetime04:59 We think about our startup success the way people tend to think about career success08:05 Sometimes, founders are just done and want to sell fast14:36 We optimize for cost and revenue over time but unwilling to invest time when it’s over18:28 We love to assume the outcome in that next hand and just carry forward22:56 Stick around and work on every angle to achieve exponential liftoff26:41 Pay attention to what you have in your hand at the moment30:07 Successful Startups achieve success due to a ton of factors lining up at the same time

In today’s Startup Therapy Podcast, Wil and Ryan talk about founders allowing open discussion of socio-political issues inside the workplace. Over the years, societal and political issues are topics that can either encourage healthy discussions and debates within the team or instigate friction and divide within the company. The question is, HOW do we talk about these issues? Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:25 Socio-political issues in a workplace03:02 It’s important how and where we talk about these issues05:55 Areas where we can start to have more productive conversations10:51 Focus has a cost and it’s not that simple14:44 Some socio-political issues are directly impacting people’s focus 11:3918:03 Not all founders really care about other people’s issues outside of work20:28 There are a lot of people in power that just don't understand these issues25:43 Why this idea of just oppressing everything is just a broken hammer32:00 Issues aside, what are the employees trying to accomplish?36:34 Not everyone wants to be pulled into these discussions

In today’s Startup Therapy Podcast, Wil and Ryan ask, is it too early to get an advisor? Many Startup companies invest in an advisor to tap into connections that can possibly help raise additional capital. Yet, this investment does not promise successful returns because some introductions don’t end with the results founders are hoping for. The anticipated business meetings are never set.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:28 How often were you asked to be a business advisor?03:55 What's the guarantee that they want to know you?07:08 If getting an advisor is just for raising the capital09:31 One-sided conversations: what’s the biggest thing you can have getting an advisor12:10 What if you make the introductions and nothing comes of it?16:18 Ponder first if it’s the right time to invest in an investor18:46 When people know more than you do, they just seem like geniuses22:37 You can’t qualify an advice on a topic you’ve never understood28:58 A good advisor will tell you what questions you should be asking35:25 Advisors aren’t that bought in and won’t fully care

In today’s Startup Therapy Podcast, Wil and Ryan talk about at what cost Startups are built on. What people often see is it’s all about raising money and getting external financial support, that additional funds are more than enough to keep the business going. But what people don’t see is the physical, mental, and emotional health that are being spent alongside a bloating debt. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:24 The true currency spent when building a Startup05:10 What are the personal costs for the founders?09:05 Raising more money doesn’t make things any easier19:31 Our Startups pull our health on different directions23:58 Founders slowly lose connection with close relationships29:00 Are you doing better than before you started your business?33:13 If you’re well-being is failing, your Startup success won’t amount much

In today’s Startup Therapy Podcast, Wil and Ryan talk about imaginary debt. A lot of founders are tied to this idea that employees will commit the same level of sacrifice as they would for the company. And that people will appreciate what they do and stick around no matter what happens. But it’s all an illusion. No one can actually match a founder’s willingness to sacrifice everything for the Startup. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:48 When you feel indebted to the people in your team06:26 Your team’s sacrifice is exponentially different from yours09:43 Everyone else is going to be looking out for themselves13:23 Founders find it difficult to get out of unhealthy situations17:26 There is a point at which feeling indebted has a limit20:28 No one actually takes care of the founders25:27 The endless “I can’t” that binds the founders 29:11 Creating your own phantom conversations30:09 You have zero right to expect that your sacrifices will be appreciated34:39 Massive loyalty dissolves when a better offer comes38:31 How to break free from the imaginary shackles

In today’s Startup Therapy Podcast, Wil and Ryan talk about the most dreaded outcome - a failing Startup. When a business fails, founders often wallow over how people react and what they can say about the situation. The adverse reactions don’t matter. What should matter is who stays to help pull you out of the rubble. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:19 Understanding how founders feel when a Startup fails05:44 When you can’t deal with how people will process the failure10:22 The Steve Jobs interview and dealing with criticisms12:05 Do the people you’re concerned about actually have a voice in the situation?17:14 Only founders who failed can sympathize with you21:47 Surround yourself with people who knows what you’re going through25:45 As a founder, how do you reach out?29:58 When one founder is down, other founders should empathize and help

In today’s Startup Therapy Podcast, Wil and Ryan talk about the pressures of leading a Startup team. It’s a Founder’s job to make difficult and unpopular decisions, even unconventional ones, which may merit the team's unfavorable reactions. Over time, these unpopular decisions make a Founder less likable. So then, at what point will being likable still matter?Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:30 As we lead, how important is it that we're liked?05:29 Making fundamentally unpopular decisions to grow11:56 When we’re starting, we build good relationships with people16:00 You’re a cool boss but you aren’t invited in team lunches19:23 The expectation for you to say ‘Yes’ all the time21:47 What about when decisions don’t map back to you?23:23 Even if you aren’t liked, you have to be respected28:39 Everyone loves you, but you’re doing a bad job32:43 Make difficult decisions but still empathize37:22 As the organization grows, there will be more people not connected to you39:39 Things you can do to seed some goodwill

In today’s Startup Therapy Podcast, Wil and Ryan talk about admitting you made a mistake. Oftentimes, it becomes difficult for leaders, including founders to admit that they’ve made the wrong decision or chose the wrong option. It’s the kind of vulnerability that no one wants to show. But if leaders can’t admit that they are wrong, no one else in the organization will. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:09 Founders fundamentally mess up and that’s okay04:54 The longer you admit that something’s wrong, the worse it gets10:32 COVID pushed organizations to strategically respond to the situation16:26 Make people understand why you made a mistake20:49 If founders can’t admit that “I messed up”, no one else will23:25 When something goes wrong, it matters how you talk about it28:23 Vulnerability comes with issues, but comes with benefits as well

In today’s Startup Therapy Podcast, Wil and Ryan talk about the qualifications of becoming a founder. It turns out; anyone can become a founder. Having the idea and vision for your Startup is easy, but building a business out of nothing, dealing with potential issues and challenges, and getting started aren’t as easy. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders Send an email to [email protected] What to Listen For00:00 Intro00:49 Congratulations on our 100th episode!02:31 Recalling the early episodes04:19 The topics are more focused on the Founders08:43 Who is qualified to be a founder?13:31 You have to be a guru when you start a business16:50 Don’t be all things to your Startup18:27 95% of all Startups is guesswork 22:57 Your expectations should include the iterative process26:52 There’s just so much we haven’t seen28:43 Unless you’ve been part of a fundraising process, you won’t understand how it works33:25 Get third-party perspective34:30 There's no parody in consequence

In today’s Startup Therapy Podcast, Wil and Ryan talk about selling a founder’s vision. The real struggle lies in convincing people that your vision, your idea can solve an existing problem. Startups often fail when the customers who are supposed to benefit from the product do not understand how it can serve their needs. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders What to Listen For00:00 Intro00:51 Back at a time when people ask: “What the hell is an internet?”06:15 It won’t matter what you’re selling if the approach isn’t relevant08:50 Ask yourself: “What problem are you solving?”14:57 Founders often fail to set the problem that could potentially solve itself19:14 Looking back into a business proposal that addressed an unrelatable problem22:53 It’s essential to consider who you’re talking to when presenting your vision26:49 The people you bring in will have a major definition of the company’s future28:46 Be ready to explain how your vision will benefit others31:25 If you can’t clearly define the problem, you can’t move forward36:26 Do not assume that people can easily connect the dots

In today’s Startup Therapy Podcast, Wil and Ryan talk about planning for a downside strategy. Having a downside strategy allows for open conversations to conclude effective upside plans and address issues level-headedly. It’s a clear and sound path for founders to clean up a failing Startup.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginJoin our Network of Top Founders What to Listen For00:00 Intro00:29 Dealing with downsides forces difficult conversations05:33 Downside strategies are a big part of any Startup11:05 What is your tolerance for tough decisions?18:14 Duration and severity of a downside21:30 Know how to deal with a failing business26:27 Establishing a threshold can make a difference29:40 “When we worry about things, we tend to scale up to the biggest worry.” - Wil 32:10 Having a downside strategy allows for a powerful upside strategy36:09 Build detailed downside strategies and be open to conversations

In today’s Startup Therapy Podcast, Wil and Ryan talk about the correlation between money and happiness. Being successful and having a lot of money doesn’t equate to genuine happiness. More often than not, it’s a fleeting distraction from other issues that require attention. Money can only give you exhilarating yet passing moments. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginWhat to Listen For00:00 Intro00:10 Once you have money, are you truly happy?04:15 With or without money, there’s always an issue to resolve07:10 Wealth can only take care of the pain, but not buy real happiness10:22 Money distracts you but can’t fix you13:52 When the excitement fades, what else is left?17:55 Spend time on your yourself, don’t get stuck on an outcome21:48 At the end of the day, you’re still the same person24:09 Analogy on the happiness of pursuit 27:10 Every milestone reached is often a fleeting moment

In today’s Startup Therapy Podcast, Wil and Ryan talk about finding the right cofounder. It remains a challenge for Startup founders to find a business partner that doesn’t just have the best ideas, both should also see eye to eye when it comes to company growth and career goals.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginWhat to Listen For00:00 Intro00:35 Are you working with the right cofounder?05:21 Not everyone is cut to be a founder10:06 The consequences of committing to the wrong person12:13 Signs that the partnership isn’t working16:12 When there is friendship but lacking work partnership 23:17 It’s not about perfection, there are shortcomings too26:41 You can’t test your cofounder until sh*t happens32:24 Questions to ask when looking for a cofounder36:06 How to prepare for a new partnership38:36 Getting into an amicable breakup through conversations42:08 Present terms that are beneficial for both party46:52 It doesn’t benefit you yo blowup on someone

In this Startup Therapy Podcast, Wil and Ryan ask how much is too much when it comes to Founder transparency? Why many inner workings of your company should be on a need-to-know basis, how being a leader can mean holding your emotional cards close to your chest, and when being completely open can be too much.Sign up for the Startups Newsletterhttps://www.startups.com/newsletter

In today’s Startup Therapy Podcast, Wil and Ryan talk about the disadvantages of having wealth. People are drawn to Founders who are successful, who have money to spare. Most of the time, people, including family, expect you to settle their financial issues just because you have the money. It reaches a point where you’re expected to spend your money and not expect anything in return. The toxicity is just too much when it happens too often.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginWhat to Listen For00:00 Intro00:26 Relationships and wealth05:38 When people is all about wanting something from you07:51 Some family members expect more from you13:38 Founders are being judged by their wealth16:41 Once you give something, you’re expected to give more19:10 People tend to want to have your money too23:24 Either way, you’ll be judged by how much cash you have26:32 Assumptions are made when you have the means and resources29:45 People with money can’t just give away what they have33:29 The calls are now about financial matters, no more sincere connections36:31 Everyone just wants to take from you but not willing to give back

In today’s Startup Therapy Podcast, Wil and Ryan talk about commitment. There is a limit to the expectation you can set on others, and that your passion and commitment may not be as intense for the rest of your team. There are certain aspects of your Startup that you’ve got to shoulder on your own. After all, a founder’s superpower is the intensity of his commitment. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:Startup Therapy Podcasthttps://www.startups.com/beginWhat to Listen For00:00 Intro00:26 What is founder commitment?03:53 The insane level of expectation founders have07:22 Startup downside: letting go of people12:00 Even with commitment, some people aren’t willing to deal with the downside15:15 Not everyone shares the same expectation within the organization19:02 Don’t set high expectations for other people24:58 You can’t manipulate people into sharing your dream25:57 Commitment is a founder’s superpower 27:16 There are certain things only founders should worry about

In today’s Startup Therapy Podcast, Wil and Ryan talk about the ugly truth about comparing your success to other businesses. When founders meet, the first person to speak often sets the tone of the conversation; many don’t even want to dig deep into the hardships one must endure to attain success. And is money the only metric for growth?Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:https://www.startups.com/beginWhat to Listen For00:00 Intro00:25 Drawing comparisons against other founders03:03 The focus is often on the negative instead of what’s working06:58 Comparing your performance to others just doesn't’ make sense11:11 We often see the outcome but not the amount of work done13:50 How do you perceive where you need to go?17:04 At what point can you say, “I’m good”?20:36 When a company grows, the focus shifts internally23:05 Growth just for the sake of growth isn’t always true26:12 Doing well with the things you really care about28:50 Quit glossing over to avoid tough conversations 31:22 When things go down, which parts will matter?

In today’s Startup Therapy Podcast, Wil and Ryan talk about getting rich without selling your business. They discuss how getting too focused on getting rich causes missed opportunities, is selling your Startup necessary, the cash stacking effect, and spending money you haven’t earned yet. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:https://www.startups.com/beginWhat to Listen For00:00 Intro00:09 Myth: Build big things to get rich03:55 You miss other avenues for growth when you’re too focused on getting rich05:31 The cash stacking effect11:44 Getting regular pay versus never getting paid while running a startup13:22 Planning to spend money you haven’t earned16:52 “Aim for the likelihood of the outcome, not the size.” - Ryan Rutan19:11 The broken idea of how to become rich23:07 When did you start to feel rich?28:26 Do you need to sell to get rich?29:19 If there isn’t a need to, don’t sell

In today’s Startup Therapy Podcast, Wil and Ryan talk about getting through a Startup failure. While your mind can make it seem bigger than it is, most people won’t remember when a business shuts down, and that processing your emotions include assessing your failure to get back up! Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:https://www.startups.com/beginWhat to Listen For00:00 Intro00:10 What does failure really look like?04:57 This is how people think about failure09:21 When you’re focused on not failing instead of succeeding11:19 Unpacking two filters of Startup failure15:45 Your Startup failure isn’t as big as you think it is20:58 What happens when you freak out22:31 Over time, people forget about a company shutdown26:34 Process the emotions, but get back up!29:32 Unpack and assess your failure to manage it

In today’s Startup Therapy Podcast, Wil and Ryan talk about the hard part of being a founder - nobody understands what you do. Founders need people they can talk to about their job, someone mentally and emotionally willing to support their journey, and why the lack of support can hold them back. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:https://www.startups.com/beginWhat to Listen For00:00 Intro00:12 Does anybody actually understand what founders do?03:13 “Communication is the burden of the sender.”04:52 Imagine being a founder is a job interview08:25 Americans tend to ask people what they do10:08 Only founders understand their fellow founders13:23 It’s different when you cause everyone to lose their jobs17:13 When you don’t get the support that you need20:55 This is where founders are held up25:12 Keep people who truly understand what you do

In today’s Startup Therapy Podcast, Wil and Ryan talk about the cost of ambition. They discuss the levels in which aspiration is achieved, how starting a business involves: a series of unique conditions, the three basic levers of ambitions, and the uncertainty of the returns a founder has to consider. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:https://www.startups.com/beginWhat to Listen For00:00 Intro00:21 There are things that you may not achieve at all03:25 Not having something sometimes doesn’t matter05:52 It’s not just ambitions, it involves a series of conditions to reach a certain threshold11:44 “There are levels to which ambition alone can achieve.”15:39 The cost of ambition becomes more than just our time21:42 You know the cost, but what about the returns of your ambition?26:45 Once you achieve something, how much are you willing to work for the next32:17 The three basic levers of ambition

In today’s Startup Therapy Podcast, Wil and Ryan talk about the truth about Startup shutdowns. Shutdown cycles always happen to Startup businesses, several bad decisions don’t mean a complete failure, and second chances can happen when you’ve asked the critical Why’s.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:https://www.startups.com/beginWhat to Listen For00:00 Intro00:59 Startup shutdown is always part of the process07:05 Shutdowns had been happening even before COVID12:15 When you assume you’re a failure because of several bad decisions14:27 How bad was the mindset?16:47 What was the turning point?19:56 Rising back after a 48-hour downtime24:59 Do-overs are what defines some of the great companies28:46 Tips on how to restart a Startup34:06 The looming danger when you can’t ask all the critical “Why?”35:54 It starts with seeing a version 2 of the business to restart

In today’s episode of Startup Therapy Podcast, Wil and Ryan talk about when it’s too late to launch a Startup. How gained experience equips founders to get through Startup challenges, the liabilities and the stakes involved when founders start late, why our 20’s is the golden decade to test and fail.Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:https://www.startups.com/beginWhat to Listen For00:00 Intro00:22 When is it too late to launch a Startup?04:42 Deciding an end-point to your career07:20 Our 20’s is a one-time get-out-of-jail free card11:55 Gained experiences in building a Startup is the baseline of future endeavors18:20 Missing important family moments22:49 Mishaps will happen but the experience will get you through25:09 Understanding the consequences of knowing the pattern from start to finish28:45 You’re less employable at your peak age31:47 Not all founders started at their 20’s34:44 Starting in your 40’s is the most challenging times37:00 50’s is the most expensive stage for founders41:58 One of the challenges is, if not now, when?43:09 Why young founders pivot so much45:45 Passion and mastery produces different outcomes

In today’s episode of Startup Therapy Podcast, Wil and Ryan talk about the emotional toll on Founders when they sell their business, how to spend time when the Startup is gone, losing authority and level of importance, if there’s a way to prepare to become an ‘exited’ Founder. Sign up for the Startups Newsletterhttps://www.startups.com/newsletterResources:https://www.startups.com/beginWhat to Listen For00:00 Intro00:25 Some of the potential downsides when selling a Startup03:38 How much our Startup is tied to our sense of purpose09:18 Concentration of excitement and purpose13:21 That feeling of being needed17:30 The horrible feeling of never being able to do it again20:20 When you become an “ex” or “former” CEO26:23 Without a business, how will you spend 16 hours a day?30:40 Equating work hours to family time34:12 Preparing to become an ‘exited’ founder