The series of founder’s dilemmas as shown in Startup Ssn 2(Tv Series)

I started watching Startup after a recommendation from a friend. Having watched Silicon Valley earlier this year, I blindly assumed the two series would be largely similar in terms of concept. And while they are in the sense that they both highlight different challenges and decisions startups go through, Startup is a far fetch from Silicon Valley.

It is based on a desperate banker, a Haitian-American gang lord, and a Cuban-American hacker all forced to work together by circumstances. In my opinion,the new season released last month is much better than the first season. The crime and drama is heightened to a new level and I could never predict at some scenes what was going to happen next.

But this is by far not a movie/series review. Because I’m reading the Founder’s Dillemas by Noam Wasserman, I saw a lot of the challenges faced by startups and especially founders as highlighted in his book. As he famously divides them, I’ll use his 3Rs to breakdown this new season and separate the bullets & cocaine from the actual lessons you can learn if you’re running your own startup.

Startup is an original TV series from Crackle

R is for Relationship Dilemmas

There are many instances of relationship dilemmas that crop up in this new season for instance;

i. Vera and Alex-Board Lead vs CEO

We see a dilemma between Vera (Gencoin’s VC lead) and Alex (Gencoin’s CEO). As Alex continues to discover the ins of how his board really works and their ‘evil’ plans for use of his tech to run their crime empire, he faces a dilemma of choosing to stay with Vera and be the face of the company or exit. He chooses the buyout and asks to leave as soon as Darknet reaches good traction. But Vera refuses to let him go saying they need to get to 10 Million active users before they can let him go. This decision comes up again at the end where Alex gives Izzy(rival & competitor cum new partner)incriminating information about the criminal empire and digital evidence that the FBI then use to bring everything down.

While this is a different kind of relationship, it’s also similar to the dilemma Steve Wozniak faced with Steve Jobs at the running of Apple Inc brought about by differing values between the two. Leaving Wozniak doing things without Steve’s knowledge and the two former best friends almost crushing their social relationship.(pg 109)

ii. Social vs Business relationship dillemmas

Ronald Dacey-Out of the three founders in the story, Ronald’s story is definitely the most unique and challenging. He has different dilemmas including fights with his wife and family as he tries desperately to create a new life for them. But his family is dug deep into the crime wars to just up and leave and become a legitimate entrepreneur. His wife doesn’t believe so much in his new venture Araknet(a new dark net) that was ideated by his only son Touie, who is sadly shot and killed in the season.

At the end Ronald proposes a buyout for himself as Araknet and Gencoin merge so he can leave the streets and start a fresh life for his family. But when presented with the papers, he chooses not to go ahead with the plan citing that he owes it to Touie who came up with the Araknet idea to see it to completion.

Another complicated relationship Ronald faces is one shown when Ronald finds out his crew know about his proposed buyout. His drug crew see the streets as a family where if one wins, they all win and thus they start talking of the new cars and ways they’re going to spend Ronald’s buyout money. And just for a few seconds, you get to see Ronald’s face as he thinks of his allegiance to his crew vs his obligation to his family.

Ronald Dacey and his son Touie( Father & Son)

Romantic relationship- Izzy & Stella

Izzy has a hard time keeping real relationships. And when she’s confronted with a hiring dilemma as the team needs more people to execute their idea, she thinks of Stella, her old lover and developer. Only problem is Stella is married now and living the good old boring life. Izzy keeps pushing Stella to leave her life and come join the new startup. Eventually she agrees and the two seem to be happy. This is until their car is abushed and shot at and Izzy thinks about how she had not considered the business factors when asking Stella to join them. Their social relationship suffers as Izzy wants Stella out of the company so she can be safe but Stella refuses to go. Wasserman discusses in depth the situation “playing with fire’ as he calls it and how founders should not mix business with pleasure. Unless they take certain actions to protect both.(pg 113) He summarises by Paul McManus, “ In my opinion, those who found companies with friends will (a)lose the company, (b) lose their friends or (c lose both.” and pg 108, “ I think you’re much better off founding with and hiring strangers…..”

Another romantic/social dilemma is the one Wes Chandler’s daughter faces when his dad realises who she’s dating at the company party. He tells her to stop dating Nick the company CEO as it will not end well. But she rejects asking his rather if he’s just scared he will lose her. Interesting to see how this would play out in real life. One such example given in the book is Evan Williams, Cofounder of Blogger, and the challenges he faced because he worked with his girlfriend. Williams narrates how the relationship turned sour as many dilemmas cropped up such as decision making, eventually leading the company to failure and their social circles crippled.(pg 105)

R is for Role Dilemmas

i. Investor vs CTO

Izzy(CTO kinda) vs the new investor Wes Chandler they are forced to get(or even lucky to considering their first business failure). Izzy is very attached to all of her work and has issues letting go of authority. First when they have to choose roles for the new startup Araknet. Izzy assumes she will automatically be the new CEO although the team disagrees. More of how this dilemma can be solved in the book as Wasserman discusses how executive titles should be allocated in startups.(pg 121).

Secondly there’s a relationship and also role dilemma when the team has to decide whether they should have truce with their biggest competitor(one who tried to even kill them!) and merge to become the biggest currency & commerce giant in US. Understandably Izzy has reservations because I mean the guys killed her sister to prove a point! But the team insists business wise it makes sense in order for them to achieve their scaling goals. At one scene, Izzy is seen to be hurt when her first team(the 2 founders) agree with Wes(the new guy) and she proposes that they go talk separately about it but the new investor Wes states that they are now no longer 3 but 4 and they agree to a vote to settle it.

ii. Vera & Bodgen

This brother & sister duo face their biggest dilemma yet as Bodgen thinks his sister has grown too soft when she chooses ‘gentle’ ways to deal with the competition(Araknet) much to Bodgen’s disappointment. Vera even calls to the country their company(nice for crime empire)’s head to settle things down. But despite clear orders for Bodgen to let the fight go, Bodgen collects his top men and they raid Araknet’s home and have a shootdown where Ronald is almost killed and Bodgen is killed.

iii. Ronald & Wes (COO & Investor)

From the start Ronald has never clearly had a defined job title and job description. How would you describe the drug lord who shoots and threatens everyone for you? Despite the fact that Ronald has done alot for the team including putting his team in danger, the new investor disrespects him and we see Ronald feeling like an outsider in his own company that he brought together. This dilemma comes from the mix between social relationships and business relationships that Wasseman talks about in pg 119 & later on in the book. Most startups actually don’t clearly define roles and decision making structures for the new team that lead to such issues.

The new team

R is for Reward Dilemmas

Reward dilemmas are not as intense in the series as of this new season.

i. Ronald’s buyout- When Ronald asks for a buyout from Araknet, the team has to decide what amount or package to allocate to him based on his contribution to the company. While we’re not told the exact terms, Nick(CEO) calls it a healthy offer.

ii. Alex’s buyout- The young coder decides to leave the corrupt company and asks for a buyout as Darknet’s traction picks up. His ask is denied by Vera the Chairman of the Board until he meets her demands as they were stipulated in his buyout/exit terms and conditions document. He is thus stuck with the company and can’t leave until Darknet achieves the stipulated numbers.

All in all, I truly enjoyed this new season and as a growing entrepreneur too, I can only wish and pray for more startup movies and seasons from the ooh great Hollywood!



HR Generalist| Founder @JobonicsHR | Where HR, Tech & Design meet | 🇰🇪 IVisit for more info.

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Stella Ngugi

HR Generalist| Founder @JobonicsHR | Where HR, Tech & Design meet | 🇰🇪 IVisit for more info.